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Holiday Rentals in Orleans

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    Nauset Beach and Privacy1 / 12
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    ESTATE OVERLOOKING PILGRIM LAKE IN ORLEANS! LINENS INCLUDED! DOG FRIENDLY!1 / 41
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    This immaculate home is located in a quiet neighborhood with just a .2 mile walk down a sandy path to Skaket Beach. It is also close to the bike trail and nearby shopping and restaurants. The home features an open floor plan with skylites, a spacious screened porch with seating, and a large back...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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    About this property
    Located beside Cedar Pond which is great for fishing, this home offers all of the privacy and convenience you could ask for while enjoying your Cape Cod vacation. Walk to Main Street and the Bike Trail in less than a half mile or bike to beautiful Skaket Beach - just a mile away! This home has a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This custom designed home was renovated just a couple years ago and is newly furnished and tastefully decorated. It has all the comforts and conveniences of home: bedroom A/C units on each floor; GenAir cook top with grill and griddle; double oven; gas & charcoal grills; 4 TVs, including new 36”...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Built in 2013, this beautiful home abuts conservation land and sits at the end of a cul de sac offering great peace and quiet for your vacation. The interior is clean and nicely decorated and offers amenities like Wifi, cable tv and Central A/C, (central a/c also in lower level). The first floor...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    This 3 bedroom, 1 bath Orleans home is within walking distance of picturesque Rock Harbor and Cape Cod Bay. The first bedroom features a king sized bed, the second a double sized bed and the third has one twin sized bed. The spacious living room also offers a pull out sleeper sofa for extra...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This delightful, newly renovated and furnished cottage is situated on 1.5 acres of land and offers peace and quiet - right on Pilgrim Lake in Orleans! Central A/C has been added for the summer season!!! This two bedroom, one bath cottage is perfect for a couple or small family of four. Take in the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Newly Listed and Newly Updated, this is the rental you’ve been looking for!! Situated in a secluded wooded neighborhood, not far from shops and restaurants. Perfect home base, just 1.7 miles from popular Skaket Beach on Cape Cod Bay, 1 mile from Rock Harbor sunsets, and the bike path is just .3...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Smoking allowed
    About this property
    This 3 bedroom Cape Cod charm is bright and airy. This beautiful summer home is appointed with your comfort in mind and decorated with your love of Cape Cod at heart. Simple luxuries include hardwood floors, flat screen TV, DVD, Ping Pong Table and window A/C units in all of the bedrooms to keep...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    This comfortable 3 bedroom ranch is within close proximity to Little Pleasant Bay. A private walking path brings you to a sandy beach just minutes from your doorstep. The property features three bedrooms and one bath and sleeps up to 6. The first bedroom features a queen sized bed, while the other...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Set on a rise in a quiet South Orleans neighborhood, this single-level home offers plenty of privacy and living space: a living room opening to the backyard deck, a dining room, kitchen breakfast bar, and a family room leading to a sunroom that also opens to the backyard deck. Ductless A/C,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    New bedroom suite, recently expanded living room, flat screen TV's and 2nd full bath! This quaint 3 bedroom, 2 full bathroom Cape Cod Vacation Cottage is located on a spacious corner lot located just 3/10 of a mile from beautiful Skaket Beach in Orleans. Enter into cheerful living room, here you...
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    Orleans, Cape Cod 2653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the comfort of this conveniently located and well-appointed newer home. Nauset Beach (oceanside) with full amenities (restrooms, outdoor showers, Liam's for seafood, burgers, ice cream and more) is just a short drive (3.5 mi) from the house. Skaket Beach on the Cape Cod Bay with its long...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This recently renovated 2 bedroom,1 bath cottage is nicely appointed in a prime East Orleans location, convenient to beaches and shopping. It is situated across the street from Town Cove and Asa's Landing and offers views of the water. The cottage has lovely grounds and gardens to enjoy, as well as...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This 2 bedroom condo is equipped with kayaks and canoes right on the association dock. (First come first use with a few other condo units.) Renovations include air conditioning, new hardwood floors, new windows, outside shower, and additional half bath. The main level offers a fully stocked kitchen...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    This roomy and attractively appointed 4 bedroom, 3 bath home offers comfort and privacy in a quiet South Orleans setting. A private dock with boat slip for a dinghy is available at the end of the cul-de-sac. It is a great location for kayaking. Other extras include: a high chair, pack n play, ping...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Nauset Heights! Absolutely lovely, newly built guest house located just under a half mile from the sandy shore of Nauset Beach on The Atlantic. Designed with the cozy character of a barn with the finer amenities of today. Beautifully detailed throughout with authentic wide pine floors, sliding...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    8 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    About this property
    With its great views of Cape Cod Bay across Namskaket Marsh from upper and lower decks, this charming and newly renovated home offers peace and privacy. Located on a cul-de-sac with a shady front yard, the house has skylights, sunlit rooms, an open loft with a sleep sofa and sliders to the decks...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 8 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Charming remodeled 1930s cottage! This home is located in the desirable and scenic Mill Pond area in Orleans with a well kept yard and wrap-around deck. House is very comfortable with single story living. Three bedrooms (brand new mattresses) and 1 and a half baths are located off the main living...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    Prestigious location within Quanset Harbor Club Association. Built on 1.3 acres and only 3 houses away from the community’s private beach on beautiful Pleasant Bay. This is the perfect property to enjoy all that Cape Cod has to offer. Home is newly furnished with a new gourmet kitchen with high end...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    Walk to Skaket Beach, Orleans Center & Bike Path, Renovated, A/C in all rooms & WIFI Mere steps to the Cape Cod Rail Trail and under a mile to Skaket Beach and the shops and restaurants on Main Street in Orleans. This charming, renovated, antique home is the perfect place to spend your Cape Cod...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Deeded access to Crystal Lake, central A/C, water views This brand new luxury 3 bedroom home with central AC sleeps 8. It is a state of the art home built in 2014 with views of Crystal Lake in Orleans. Direct deeded access to Crystal lake comes with the home through short path down from the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    This immaculate, well appointed Cape enjoys access to all of the amenities of Orleans. Its close proximity to Skaket Beach, Rock Harbor, Orleans Center and the Bike Trail make it an ideal vacation property for the active family. With three bedrooms, 2 baths and an extra sleeping area with a daybed,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    This 4 bedroom, 3 bath home sits on Namequoit River in Orleans with a private dock off the backyard offering direct access to Pleasant Bay. The first level of the home offers one bedroom with a king sized bed and one bedroom with a queen size bed. The second level features two additional bedrooms,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    About this property
    This lovely 3 bedroom, 2 bath East Orleans vacation rental is located 1.9 miles to Nauset Beach in East Orleans and just 3/10ths of a mile to Nauset Farms Market, Sundae School Ice Cream and Zia s Pizzeria. At this private and quiet location you can enjoy the beautiful outdoor living area and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Recently renovated, spacious two-bedroom home with CENTRAL AIR-CONDITIONING sleeping six tucked up on a wooded knoll at Bakers Pond. This spot offers much privacy and is less than .1 mile to beautiful freshwater swimming and kayaking on the pond. This location feels removed from it all, yet is...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming Cape Cod Home1 / 13
    (2)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Reviewed 19 August 2016
    The setting and view of the bay were perfect. Inside was uncomfortable old rickety furniture crammed in all rooms.
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    About this property
    This quintessential Cape Cod home was built in 1775 and has been in the same family for almost 200 years. Charming beyond words this home sits at the end of Tonset Road and looks out over Nauset Inlet to the Atlantic Ocean beyond. Stone walls and meadows surround this time tested property. The...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Fall in Love with this expansive 4-BR. Bow Roof House located on a country road in desirable Orleans, within walking distance to Pah Wah landing, where you can launch your boat, kayaks or canoes, or sail to the Outer Beach. The Pah Wah Point hiking trails and a sandy beach at Little Pleasant Bay...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Light and bright spacious beach house sitting on the edge of a marsh at the end of a sandy lane-- just 2/10ths of a mile from Skaket Beach! This wonderful spot offers panoramic marsh views with peeks out to the waters of Cape Cod Bay. The recently renovated main floor consists of a lovely kitchen...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This cute 2 bedroom, 2 bath waterfront condo sits on beautiful Skaket Beach in Orleans. It is a second floor, end unit with unobstructed views of Cape Cod Bay. The property features two bedrooms, one with a queen sized bed and one with two twin sized beds, as well as a double pull out sleeper sofa...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    This 2 bedroom Orleans cottage is light and bright and offers close proximity to Skaket Beach! Located in a residential neighborhood, it features two bedrooms and two full baths, sleeping up to 5 comfortably. There is a fully equipped kitchen with eat in dining area, cozy living area with flat...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Nice 2 bedroom, 1.5 bath home so close you can WALK to your own private association beach on PLEASANT BAY. When you walk in the front door you go up a few stairs to get to the main level. The first level has a nice living room/dining room, a galley kitchen, and a relaxing 3 SEASON ROOM where you...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walking distance to Meetinghouse Pond, Passive Solar This 3 bed, 2.5 bath retreat with central A/C is hidden away down a semi private drive in East Orleans. It has large sliding glass doors down one side of the home off the living room offering lots of light. Mid-century modern decor fills this...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    This light & bright newly listed home is situated on a quiet, dirt road and offers an easy 4/10th of a mile walk to Skaket Beach. It has 2 bedrooms on the first level, one with a queen sized bed and the second with 2 twins. There is also a cozy, open layout with a living area and updated, eat-in...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Renovated Gem on Town Cove in Orleans with hot tub, walk to town Peak Summer Weeks: $4,400 - $5,400 Please note:  This property rents Sunday to Sunday in summer for full-week or multiple week terms only, but is available during the shoulder-season for 3-night minimum. This Orleans home is located...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Waterfront on Nauset Harbor! Classic Cape located on an incredible property overlooking the water and beyond. Enjoy the lovely living area with fieldstone fireplace, relaxing on the spacious deck or taking the path to the shore's edge. Current updates include new carpeting throughout house,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    This charming and pristine contemporary ranch, nestled in a private wooded paradise-Mayflower Point, is minutes by foot to private salt and fresh water accesses for boating, swimming, or fishing. Launch a kayak at ''The River'', leading to Pleasant Bay and the outer beaches, or, if you prefer,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Beautifully furnished historic home in the Nauset Heights area of East Orleans. Walk to private Association beach or to Nauset Beach (public/lifeguards) on the Atlantic in minutes. Sliders from open dining room and living room to large screened porch overlooking expansive backyard. There is also a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Location, Location! Beachfront on Skaket Beach! Two bedroom ground level condo in 4-unit waterfront building. Enjoy the sandy shore of Cape Cod Bay right outside your door. There are 2 twin beds in one bedroom and two sets of bunkbeds (4 twins) in the other. This single-floor condo has a brand new...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    244 Tonset Road, East Orleans (ID#125800) 2018 Season! Adorable vacation rental located in East Orleans. This property has a screened porch overlooking the private back yard located in a nice neighborhood equidistant to Nauset Beach on the Atlantic Ocean and Skaket Beach watch the sun set over...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Newly decorated, charming East Orleans escape just a mile and a quarter to fabulous Nauset Beach on The Atlantic. This sweet two bedroom home is located on a cul de sac convenient to East Orleans Village. Enjoy grilling on the patio with family and friends and the outdoor shower to wash all that...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    On the Waterfront of Nauset Heights1 / 43
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    BY THE SEA, featured in Coastal Living magazine, is a waterfront beach house on Nauset Beach. If you like sand dunes and salty air, this is a rare opportunity to vacation in Nauset Heights, a quintessential Cape Cod beach community. Step out the door to one of the country’s most beautiful beaches....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Waterfront 4 Bedroom on Crystal Lake in Orleans. This well appointed 4 bedroom has recently been fully updated. It has central AC throughout the home and it is quite spacious! Upper and lower floors all have lake front views. The main level has an eat in kitchen with mini bar with seating for 4....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    21 Manito Road, East Orleans (ID# 114251) ~ Overlooking Meetinghouse River 2018 Season! Lovely waterfront home on Meetinghouse River. First floor includes open living / dining area, eat- in kitchen with stainless steel appliances, 3 bedrooms and 2 full baths. 1st Bedroom King Bed with slider to a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    World famous Nauset Beach is short walk from your door and the Village of East Orleans is the same distance in the other direction. You will find this home very spacious with a living room with game table, family room that boasts cathedral ceilings, dining room, large kitchen and 1/2 bath on the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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