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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 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 23
    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    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
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    Orleans, Cape Cod 02653
    1 / 17
    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 22
    4 of 5 bubbles (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
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    Orleans, Cape Cod 02653
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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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
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    1 / 40
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Newly remodeled historic home. Heated Pool, Central AC, Sleeps 12, Linens & Towels Included! Peak Summer Weekly Rates: $9,500 This beautiful 1920 Orleans home, newly remodeled and redecorated, exudes Cape Cod charm, retains its original historic character and provides the highest level of modern... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Sweeping Bay Views, Privacy, Two Full Kitchens (Pets Considered) Peak Summer Weekly Rates: $4,300 - $4,500 This unique vacation home is nestled between Rock Harbor to the east and Skaket beach to the west. The home has its own private boardwalk across the tidal areas. You'll have your feet in the... View all property information
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    Orleans, Cape Cod 02653
    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautiful Cape Cod home sits on Barley Neck, which is small peninsula just a few minutes drive to Nauset Beach. Beach sticker for parking is included in your rental! It is surrounded by Meeting House Pond and Little Pleasant Bay. This area is harbored from the Atlantic Ocean by Pochet Island.... View all property information
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    Orleans, Cape Cod 02653
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    28 Kings Way, Orleans MA (ID# 95117) 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 room with... View all property information
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    Orleans, Cape Cod 02653
    1 / 13
    4 of 5 bubbles (2) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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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... View all property information
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    Orleans, Cape Cod 02653
    3 of 5 bubbles 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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    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    Walk to the water from this private 4 bedroom, three bath home. Just 2 houses away from a private path to Little Pleasant Bay! Nestled within two acres on a gorgeous country dead end road. The sandy beach of Crystal Lake is only .4 mile walk away, Pilgrim Lake less than a mile, and a short... View all property information
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    Orleans, Cape Cod 02653
    1 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Beach, Kayaks, SUPs on Pristine Orleans Lake! (Pets Considered) Please Note: This home rents Sunday to Sunday in peak summer months Peak Summer Weekly Rates: $4,600 - $4,900 Expansive Waterfront Home on Crystal Lake in the heart of Orleans. Crystal Lake is a pristine fresh water lake located close... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    3.5 of 5 bubbles (4) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Located 1/10 of a mile from the private saltwater beach on Pleasant Bay via an Association path, this multi-level contemporary offers a peaceful retreat on Shoal Pond in South Orleans. The main level is open and bright, with a wonderfully open great room, fireplace, dining area, kitchen, entry way,... View all property information
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    Orleans, Cape Cod 02653
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    True Cape Cod Charm in every way! This 3 bedroom Saltbox is just up the road from Nauset Beach. All the upgraded conveniences you could want including granite counters, hardwood floors, washer/dryer, WIFI and air conditioning. Relax in the outdoor shower or cook on the brand new 5 burner gas... View all property information
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    Orleans, Cape Cod 02653
    1 / 32
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Balcony
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    • Terrace
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    • x
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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:... View all property information
    Location Information
    Orleans, Cape Cod 02653
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    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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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... View all property information
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    Orleans, Cape Cod
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Enjoy the pleasures of a waterfront property -- Wake up to views of a peaceful Pleasant Bay inlet from this sun-filled, modern 3-bedroom cottage in the woods. Launch your kayak or canoe to explore beautiful Pleasant Bay; fish from the dock. Use of the dock for a large boat is also possible for an... View all property information
    Location Information
    Orleans, Cape Cod 02653