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Pet Friendly Holiday Rentals in Orleans, MA

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    Travellers to Orleans are booking May dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 19
    3.5 of 5 stars (4) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    3.5 of 5 stars (3) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Located right on the shore of beautiful Town Cove in Orleans. This family home has 3 bedrooms 2 baths and a view of the water which is special. This classic Cape Cod home is one floor living with all 3 bedrooms on the main floor. The master has a Queen with private bath with a walk-in shower, BR2... View all property information
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    Orleans, Cape Cod 02653
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • ?
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    • Elder access
    • x
    About this property
    With its great views of Cape Cod Bay across Namskaket Marsh from upper and lower decks, this charming 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 from the living/dining... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 18
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
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    • Patio
    • Grill
    • Outdoor Dining Area
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
    About this property
    Charming home located on a nice wooded lot in South Orleans with lovely furnishings, central Air Conditioning, and all amenities. Just a short distance (1/4 mile) to the boat ramp on Quanset Pond with access to the saltwater of Pleasant Bay. Accepts dog with $50 pet surcharge. Additional amenities... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 13
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Outdoor Dining Area
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This wonderful 4-bedroom, dog-friendly, vacation home is located only 200 yards from Skaket Beach. This great spot offers a fully equipped kitchen, living room, sun room, two bedrooms and full bath on the first level and two bedrooms and full bath on the second level. Enjoy the nicely maintained... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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 mile from beautiful Skaket Beach in Orleans. [~]Enter into cheerful living room, here... View all property information
    Location Information
    Orleans, Cape Cod
    1 / 25
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Porch
    • DVD Player
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Truly a one-of-a-kind contemporary home on Little Pleasant Bay! Set on over an acre of wooded land, this light and bright beach home has multiple decks, a screened porch and views of the water from nearly every room. Sliders in the living room and kitchen/dining area open to a large wrap-around... View all property information
    Location Information
    Orleans, Cape Cod 02662
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    1 / 25
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Pretty three bedroom home overlooking a marsh in Orleans and only a short drive to Skaket Bay Beach. Sleeps 8 comfortably with two queens,pull-out couch in alcove and two twin beds. Enjoy cozy living room with sliders to a large deck, gas grill and lots of outside furniture. Nice master bedroom... View all property information
    Location Information
    Orleans, Cape Cod
    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    This rustic cottage is on a peninsula surrounded by salt water with views of Mill Pond. It is clearly an outstanding property offering exceptional privacy. PET-FRIENDLY, too! Very spacious yard. Enjoy boating, fishing or just relaxing. Additional amenities include: outdoor shower (private/hot... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 13
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Washer
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    • Grill
    • Parking
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Satellite TV
    • Washer
    • Grill
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    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... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 29
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Washer
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    • Grill
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Walk to the water and savor country living at this lovely home with four bedrooms and three full baths. Nestled on two acres within a private enclave along a dead-end country lane. A picturesque recreation barn completes the feel of rural tranquility. Legendary Nauset Beach, the Cape’s best, is... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • DVD Player
    • Porch
    • Washer
    • Satellite TV
    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Chill out and relax at this wonderful waterfront retreat located in Mayflower Point. This charming cottage offers wonderful views of Lonnie's Pond and Kent's Point and has its own path to Lonnie's River leading out to Pleasant Bay. Bedrooms have air-conditioning for your comfort. Perfect for... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 24
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
    • Grill
    • Porch
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beach, Kayaks, SUPs on Pristine Orleans Lake! Please Note: This home rents Sunday to Sunday in peak summer months Peak Summer Weekly Rates: $4,500 - $4,800 Expansive Waterfront Home on Crystal Lake in the heart of Orleans. Crystal Lake is a pristine fresh water lake located close to Orleans Center.... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 22
    4 of 5 stars (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • Internet Access
    • Grill
    • Parking
    • DVD Player
    • Porch
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful 4 bedroom home located in Ocean Harbor Estates that offers tennis, footpath to saltwater beach and boating access to Nauset Harbor and the Atlantic from Little Cove. A traditional Cape set up on a hill with a private back yard bordering a protected bird sanctuary. This home features 4... View all property information
    Location Information
    Orleans, Cape Cod 02653
    4 of 5 stars Reviewed 21 August 2013
    This home is spacious, clean and comfortable with great amenities. Tennis court and cove make this home an ideal location for an active family!
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Just 3 miles from downtown Orleans, you'll find yourself on a quiet road where you can have your privacy, and be less than 2 miles from one of the greatest beaches in the world, Nauset Beach. Spectacular sand dunes as far as you can see set the dramatic backdrop for the Atlantic Ocean's majestic... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 23
    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    • Internet Access
    • Patio
    • Air Conditioning
    • Sauna
    • Satellite TV
    • Private Outdoor...
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
    Location Information
    Orleans, Cape Cod 02653
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    1 / 28
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Porch
    • Outdoor Dining Area
    • Private Outdoor...
    • Satellite TV
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    New Listing for 2016! Newly updated historic home. Heated Pool, Central AC, Sleeps 12, Linens Included! Peak Summer Weekly Rates: $7,500 - $8,000 This beautiful 1920 Orleans home exudes Cape Cod charm, retains much of its original historic character and provides the highest level of modern... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Patio
    • Satellite TV
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A beautifully restored and expanded Cape Cod Home just a short distance to Nauset Beach. House is very spacious with a living room and huge great room with a fireplace. Grab a bite to eat at the breakfast bar, or you may choose to dine in the adjacent Dining Room. A breezeway brings you into the... View all property information
    Location Information
    Orleans, Cape Cod 02653