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Orleans Holiday Rentals

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    Travellers to Orleans are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 28
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    #501 Viking Cottage: New renovation, sunny secluded home with view & access to saltwater. 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... View all property information
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    Orleans, Cape Cod 02653
    1 / 46
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Luxurious Orleans Home with Private Salt Pool, Sleeps 10 (linens included) Peak Summer Weekly Rates: $9,000 - $9,500 (Rents Saturday to Saturday during peak season) Located on a large private lot in South Orleans, this luxurious property provides the highest level of amenities and diverse indoor... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    Elevated ocean views, walk to Nauset Beach. Linens included. Peak Summer Weekly Rates: $4,500 - $5,200 (Rents Saturday to Saturday during peak season) This spacious East Orleans home is located just off Nauset Beach in the desirable Grand View neighborhood. This neighborhood is characterized by... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our home is located in a quiet upscale neighbourhood close to all amenities. Walk to grocery store, downtown shopping, library, tennis courts and town field. Less than a 5 minute drive to ocean and bay. Quick access to highway and all the surrounding Cape towns. Relax and unwind at With the... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    New and upscale with guest house, walk to Skaket Beach $3,500 - $3,800 prime summer weekly rate (Rents Saturday - Saturday during peak season) This home is about a 10 minute walk to Skaket Beach or a very short drive. It's less than a mile (0.8 miles) to the bike trail also. You do have distant... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Walk to the water from this private 4 bedroom, three bath home. Just one house away from a waterview and 200 yards to deeded access to a cove off The River. 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... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    4 of 5 bubbles (1) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Breathtaking views of Nauset Harbor and tucked away at the end of a private drive. With cathedral ceilings and lots of windows, this cottage offers spectacular waterviews from almost every room. The sun rises over the dunes and harbor right into both sitting rooms and dining area...sunset is even... View all property information
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    Orleans, Cape Cod 02653
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    1 / 18
    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”... 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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    About this property
    Sweeping Bay Views, Privacy, Two Full Kitchens (Pets Considered) Peak Summer Weekly Rates: $4,300 - $4,500 (Rents Saturday - Saturday during peak season) 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... View all property information
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    Orleans, Cape Cod 02653
    1 / 40
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Newly remodeled historic home. Heated Pool, Central AC, Sleeps 12, Linens & Towels Included! Peak Summer Weekly Rates: $9,500 (Rents Saturday - Saturday during peak season) This beautiful 1920 Orleans home, newly remodeled and redecorated, exudes Cape Cod charm, retains its original historic... View all property information
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    Orleans, Cape Cod 02653
    1 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Spacious Bay Side Orleans Waterfront Home Next to Skaket Beach PEAK SUMMER WEEKLY RATE: 8,500 (linens included) Situated between Skaket Beach and Rock Harbor, this magnificent home leaves nothing to be desired. Commanding views and direct access to private beach land compliment the seclusion and... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Charming modern waterfront cottage-- now with A/C!-- located in the exclusive Mayflower Point section of Orleans where the Namequoit River meets Little Pleasant Bay. The secluded area boasts scenic water views, quiet nights and sounds of birds. The living space has a new whole-house fan, ceiling... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Overlooking the salt waters of Mill Pond and located in grand Ocean Harbor Estates! The Atlantic Ocean is just beyond this amazing waterway. Only 2 miles from Nauset Beach and 1.5 miles to East Orleans Village. This property has it all. Views, association dock and tennis court privileges. Open... View all property information
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    Orleans, Cape Cod 02653
    1 / 26
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • Waterfront
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    • x
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    About this property
    ** Please note: $500 Minimum for off-season stays!** Classic Nauset Heights! Walk to Nauset Beach & Views of Atlantic Ocean! Unique extras like rain shower, summer reading library, mid-cen artwork, mature gardens and 900 sq ft deck. New Outdoor Shower, A/C in Beds, Beach chairs /wagon provided!... View all property information
    Location Information
    Orleans, Cape Cod 02653
    5 of 5 bubbles Reviewed 25 May 2016
    Great rental property with fantastic views of Nauset Beach. Very close to main beach and a quick trip into town for anything you may need. The house itself has plenty of space and...
    5 of 5 bubbles Reviewed 17 May 2016
    Organizing a place to stay for a large group can often be difficult however this was not the case here. Kent and Nicole were always available and responsive through email to...
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    1 / 19
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    *If you can't find the dates available that you are looking for, we also have a second studio you may be interested in. Send us an inquiry and we will try to help you find the dates you want.* Beach Rose is a studio in “Holly Tree Cottages” available by world-renowned Nauset Beach. It offers high... View all property information
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    Orleans, Cape Cod 02653
    5 of 5 bubbles Reviewed 21 September 2016
    We wanted an affordable quiet place near a beach. The studio was neat, clean, right near wonderful Nauset Beach and it had everything except the kitchen sink. It was just what we...
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    1 / 23
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Secluded Cape Cottage, 3-5 Minute Walk to Beach $2,100 PRIME SUMMER WEEKLY RATE (Rents Saturday - Saturday during peak season) It's possibly one of the best values in Orleans. Located on the Bayside of Orleans, this well-maintained cottage is one of 4 homes on a 25 acre family estate located... View all property information
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    Orleans, Cape Cod 02653
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    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    This lovely Contemporary Cape sits on almost an acre of land only 2/10ths of a mile from the sandy shore of Bakers Pond and 3/10 mile from Nickerson State Park (in Brewster). Light and bright throughout, this custom home features an open floor plan, gleaming hardwood floors and full amenities--... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    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
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
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    Orleans, Cape Cod 02653
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    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. 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... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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 / 16
    4 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Private Orleans resort with water views, heated pool & spa; sleeps 14 (linens included) NEW Listing for 2017! (more photos to come when renovations are complete, these photos are from the previous owner) Peak Summer Weekly Rates: $15,900- $16,900 JUST REDUCED -- weeks of July 2nd and 9th reduced... View all property information
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    Orleans, Cape Cod 02653
    1 / 40
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Superb Pleasant Bay Views, from Large, Luxurious, Secluded Orleans Vacation Home. Peak Summer Weekly Rates: $4,850 - $6,250 JUST REDUCED -- Remaining open peak weeks price drop (click rates tab for new rates) (Rents Saturday to Saturday during peak season) Nestled in the woods of South Orleans on... 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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    About this property
    At the end of a private lane lies your secluded vacation retreat on tranquil Pilgrim Lake. Just 60 feet from the decks and living room window is your private lakefront with boat dock for swimming, boating or fishing. The main deck, overlooking the water with comfortable outdoor furniture and gas... View all property information
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    Orleans, Cape Cod 02653
    1 / 14
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This private gem sits at the end of a sandy lane wrapped in trees and bathed in sunlight. The front deck welcomes you to sit and relax and enjoy the peace and quiet and plan your next days adventure. Located less the 2 miles from Nauset Beach and slightly farther from Cape Cod Bay, this Cape... View all property information
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    Orleans, Cape Cod 02653
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    WATERFRONT on Bakers Pond! Take the path from the patio to your private pondfront to enjoy swimming, fishing and kayaking on this lovely freshwater pond. Designed as an airy contemporary cabin on 3 levels-- all with sunset water views-- this home has beautiful pine panelling and hardwood fir floors... View all property information
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    Orleans, Cape Cod 02653
    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful Open Layout with updated furnishings on Nauset Heights! Walk to Nauset Beach. Unique extras like large outdoor shower, original artwork, and private setting. See reviews and latest availability and pricing on our site: nausetrental For 2015: A/C in all Bedrooms, All new bedding,... View all property information
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    Orleans, Cape Cod 02643
    1 / 12
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Beautiful 4 bedroom home on private cul de sac in East Orleans. Pristine landscaped yard with swing set and hammock. Big kitchen that opens to the family room. Open den with tv and couches. Full bath, washer & dryer on the first floor. Upstairs has 3 large bedrooms with high ceilings and lots of... View all property information
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    Orleans, Cape Cod 02653
    1 / 30
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    Located on the bank of Rock Harbor Creek, this 5 BR, 4 Bath classic Cape has all you and your family are looking for this summer. The large second floor master suite overlooks the marsh with an attached private bedroom with 2 twins where the little ones can dream away, close to the folks. There is... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    Adorable cottage located in a beautiful, quiet area about 3/10ths of a mile from Nauset Harbor. The cozy living/dining/kitchen area features a brand new kitchen, queen sofa bed and A/C unit. The bedroom has a king bed (easily converted into 2 twins) and an A/C unit. A separate laundry area has a... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Freshwater Lakefront! Wonderful, newly renovated cottage set on 1.5 acres on Pilgrim Lake! Bright and open with cathedral ceilings, large fireplace and walls of glass overlooking the lake. This great spot offers much privacy with access to the fresh water out your back door, along with association... View all property information
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    Orleans, Cape Cod 02653
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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... View all property information
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    Orleans, Cape Cod 02653
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Incredible spot! Expansive Cape cottage on a bluff in Nauset Heights overlooking Nauset Inlet and the Atlantic with a newer upper level deck and a private stairway down to the beach. Casual Olde Cape Cod with pine panelling throughout. The main floor bedrooms consist of a large bedroom with double... View all property information
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    Orleans, Cape Cod 02653
    1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Price Range $2000-$3500 NEW LISTING! PROPERTY UNDERGOING COSMETIC UPGRADES! NEW PICTURES COMING SOON! 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... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
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    • x
    About this property
    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... View all property information
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    Orleans, Cape Cod 02653
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    4 of 5 bubbles (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
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    Orleans, Cape Cod 02653
    1 / 21
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Designed to look like an illustration from a children’s fairytale, this gracious and comfortable vacation home promises a magical vacation any time of the year. Enter through lush gardens into a surprisingly spacious, fully air conditioned home designed with relaxation, convenience, and fun in... View all property information
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    Orleans, Cape Cod 02653
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This is a unique ranch in beautiful East Orleans. It has a private small dock in Meetinghouse Pond, a saltwater estuary of Little Pleasant Bay. Fully renovated in winter of 2016 this property sits on an oversized private lot and the owner is a high end landscaper who will finish exterior hardscape,... View all property information
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    Orleans, Cape Cod 02653
    1 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy an expansive layout at this antique 3 bedroom, 3 full bath home featuring a living room, two dens, dining room, large open kitchen and much more! On the first level is a Master Suite with a queen sized bed and full bathroom, with a shower and large soaking tub. Just off the Master Suite is... View all property information
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    Orleans, Cape Cod
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Brand new renovation! Light and bright expansive ranch that has been beautifully and thoughtfully upgraded throughout. This architech-designed 'green' home is pristine and feels brand new! A few of its many highlights are its wonderful great room offering additional living space, inviting deck... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Masterfully Renovated across from Pleasant Bay (Linens Included) Peak Summer Weekly Rates: $3,500 - $3,800 (Rents Saturday - Saturday during peak season) This pristine property is located on Orleans Road in Orleans. Every room, every aspect of this newly renovated home is truly something special.... View all property information
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    Orleans, Cape Cod 02653
    1 / 14
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Rare opportunity to vacation in Nauset Heights right on the waterfront! Perfect Beach House for the beach loving family or couple. Walk out the door to one of Cape Cods most beautiful beaches. Swim, fish, sunbath or take gorgeous walks for miles along the National Seashore. This 3 bedroom home has... View all property information
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    Orleans, Cape Cod 02653
    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Air Conditioning
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    • Waterfront
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Absolutely wonderful young 4 bedroom, 3 full bath cape house with open floor plan on private and quiet cul de sac street off Beach Road. This year just got totally renovated kitchen and bath with modern amenities. Only 0.8 mile from the magnificent Nauset Beach!- One of the best beaches in Cape... 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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    • Air Conditioning
    • Parking
    • Waterfront
    • DVD Player
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    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Orleans, Cape Cod 02653