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Pet Friendly Holiday Rentals in Orleans

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    Travellers to Orleans are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    27 Matching Rentals in OrleansView all 205 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    About this property
    Classic Nauset Heights home sitting directly on the bluff with magnificent views of Nauset Beach, the Atlantic Ocean and Nauset Marsh. Short walk to bay and ocean beaches. Vintage, rustic cottage character in unbelievable location. Great value for view. Wooden farmhouse style floors throughout...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Price Range $2415-$3915* *$100 less without pet Rates include all charges; no hidden fees! The moment you arrive at this 3 bedroom, 3 bath classic cape with central a/c, you will immediately downshift into vacation gear. Sited on a knoll in East Orleans, the secluded front yard is ideal for a game...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Private Outdoor Pool (Unheated)
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    About this property
    Beautiful historic home, private mini estate. Heated Pool, Central AC, Sleeps 13, Linens & Towels Included, Pets considered! Peak Summer Weekly Rates: $9,500 - $11,000 Rents Saturday - Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home The interior of this...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Charming Cape, just off historic Town Cove. With two bedrooms down, one up, plus a child's nook, this comfortable home can accommodate 7 guests. Features bathrooms up and down; a sunny family room/dining area; fully-equipped kitchen; and a cozy living room with fireplace. Only a short walk to Asa's...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Spacious 4 Acre private waterfront estate located in the prestigious and secluded Snow Point Association with private steps down to the water. Snow Point is a small peninsula of land in Orleans bordered by Rachel Cove, Town Cove and Woods Cove. You'll experience 180-degree views of the water from...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Salt waterfront home located in the Ocean Harbor Association in East Orleans. This newly-furnished home is set on over an acre of beautiful multi-level grounds with frontage and views of Little Cove. Enjoy kayaking right from your backyard, access to the association tennis courts or deepwater...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Price $1575-$2175* *without pet $100 less Rates include all charges. This delightfully redone 2.5 bedroom/1.5 bath home located in a sought-after East Orleans location is bright and open with an unbeatable location! The front door leads directly into a large living room cooled by both a ceiling fan...
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    Orleans, Cape Cod 2653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2 bedroom 1 bath apartment with separate private entrance, driveway and deck. Living room, kitchen, and laundry. Queen bed in one room and a double bed in the other room. Optional air mattress can be set up in living room to sleep 2 more if needed. Window AC units in bedrooms. Ceiling fans in...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    AT SKAKET BEACH! This charming renovated 1927 Cape has ample room for 6, a master bedroom with a vaulted ceiling and a private half-bath, plus a lovely wraparound porch with hammock. The sunny interior features newly-painted floors, comfy furnishings throughout and excellent amenities, including...
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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 8 Quick View
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    50 Keziahs Lane Orleans 4 Bedrooms 3 Full Baths Nauset Beach not far away. 2017 Season! Charming, peaceful and gracious 4BR/3BA home on a dead-end private road! On two semi-secluded acres abutted by conservation land, and 200 yds from bay inlet and nature reserve with a mile of waterfront, deeded...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    20 Deerwood Lane, East Orleans, MA (ID# 120896) 2017 Season! Wonderful Home in East Orleans with central A/C. Walk to restaurants or Sundae School after a relaxing day at Nauset Beach. This dog friendly (with homeowner approval) home features lots of room with 4 bedrooms, hardwood floors...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    28 Kings Way, Orleans MA (ID# 95117) 2017 Season! Adorable 3 Bedroom, 2 Bath Cape style home close to Skaket Beach. Convenient to Nauset Beach, Orleans Town Center, and the bike trail. Main level includes large living area, eat in kitchen, bedroom with two twins and full bath. Second level has main...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    61 Captain Linnell Road, Orleans, MA (ID# 100002) Near Skaket Beach 2017 Season! Spacious, beautifully updated, dog friendly home near Skaket Beach on Cape Cod Bay. Large granite and stainless kitchen opens to dining area, living area and office. Sliders to deck, brick patio, back yard and fire...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This nicely furnished, pet-friendly home is located on a quiet wooded lot close to the Rail Trail, center of town and Skaket Beach. The first level of the home features an updated kitchen with dining table, living area, full bathroom with tub/shower, and one bedroom with two twin sized beds. The...
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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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    **2 WEEK MINIMUM RENTALS ONLY**This is a gorgeous contempory home with a path to your own private beach on Pleasant Bay. The house features 3 bedrooms that all have ensuite bathrooms and their own decks with waterviews. The lower level has 2 bedrooms each with 2 twins and the 2nd floor has a queen...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Located in the desirable Captain Linnell area of Orleans, this home offers one floor living, a large yard, and is pet friendly! This lovely 3 bedroom, 1 bath home is just .3 miles to beautiful Skaket Beach and features cable TV, wireless internet and air conditioning! The Master Bedroom, just off...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxury 6 BR Home W/ 60 Foot Private Pool1 / 23
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
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    • Sauna
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This warm and inviting 6 bedroom, 4 bath home sprawls over 4 stories of comfortable rooms with spacious, open living areas and a private, fully fenced back yard. Perfectly located in South Orleans, the house is just minutes from the Lower Cape villages of Chatham, Brewster and Orleans. A beautiful...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    This adorable cottage is situated on the bluff overlooking Nauset Beach, on the water on Nauset Heights. Short walk to both inland waters and Nauset Outer Beach. This property has panoramic ocean, beach and water views. Property type: House Room type: Entire home/apt Accommodates: 8 Bathrooms:...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This beautiful Cape Cod home sits on Barley Neck, which is small peninsula just a few minutes drive to Nauset Beach. It is surrounded by Meeting House Pond and Little Pleasant Bay. This area is harbored from the Atlantic Ocean by Pochet Island. From this location, you are walking distance to the...
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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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    Price Range $1875-$2475* *without pet $100 less Rates include all charges; no hidden fees! New Bedroom suite, recently expanded living room, Flat screen TV's and 2nd 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...
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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 6 Quick View
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    This 3 Bedroom 2.5 bath retreat with Central AC 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 clean lined living space. Passive solar compliments...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    NEW LISTING!!! This is a well appointed 3000 square foot home in South Orleans, minutes from Rt. 28. Easy access towards Nauset and Skaket beach or Pleasant Bay. The downstairs includes a master suite with King bed and ensuite, full open kitchen and dining room, kids play room, laundry / mud room....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Meticulous Modern East Orleans Home, Water Views, Pets Considered Peak Season Weekly Rate: $7,700-$8,000 New Listing for 2017! Rents from Sunday to Sunday during peak weeks The height of modern luxury in East Orleans, this home has tremendous views of Nauset Inlet and the Atlantic Ocean beyond. The...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This Pet friendly home is located just 0.8 miles from Nauset Beach. Enter into a charming, warm home that offers two spacious living areas. One is a bright great room with cathedral ceilings, sectional seating, big screen t.v and game table. Head into the living room where you will find a cozy...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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