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Orleans Luxury Vacation Rentals

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    Travellers to Orleans are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    39 Matching Rentals in OrleansView all 264 rentals
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    10 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    6 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    Private 1.4 acre East Orleans compound with direct saltwater access The ultimate vacation escape - enjoy fresh saltwater breezes and spectacular views from this beautiful 1.4 acre estate on exclusive Snow Point in East Orleans. The compound features a stunning main house with enclosed patio and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 18
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Come to your very own private resort on Cape Cod. Located directly on Nauset Harbor on the Eastham\Orleans town line, The Jeremiah House is the place to be for your quintessential Cape Cod getaway. This luxury home is the perfect convergence of classic old Cape Cod architecture and charm with...
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    Orleans, Cape Cod 02642
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Stunning cape contemporary style waterfront home with walls of glass and panoramic salt water views from most every room. Association Dock for access to Town Cove and beyond. This home was completely renovated with designer high-end kitchen, gleaming hardwood floors, custom fireplace, and every...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Cape Cod elegance describes this beautiful, expansive home which sits peacefully at the end of the cul-de-sac adjacent to a cranberry bog. Ideal for the larger gathering with its great room with soaring cathedral ceiling, gorgeous eat-in kitchen, spacious TV loft, screened porch, deck and patio....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Nauset Heights! Classic Cape Cod beach house overlooking the Atlantic. Expansive great room with fieldstone fireplace, wrap around porch, and views from practically every room! FRIDAY to FRIDAY rental.
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    20 Hayward Lane, East Orleans (ID# 108991) Close to Nauset Beach MeetingHouse Pond, Pleasant Bay and Village of East Orleans 2018 Season! Enjoy this lovely, large, sun-filled home in charming East Orleans on a spacious, 1.5 acre private property with saltwater views of Frostfish Cove (leading to...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Access to small private beach and kayak launch in East Orleans This beautiful and well appointed 5 bedroom has recently been fully remodeled. There are sweeping views of Nauset Harbor stretching all the way to Nauset Light. Beautifully redone with an architect's eye, it boasts full central AC,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    Brand New Home, Heated Pool, Sleeps 12, Linens & Towels Included! Peak Summer Weekly Rate: $12,000 (Rents Saturday - Saturday during peak season)   This brand new East Orleans home, provides the highest level of modern amenities in a great location close to Nauset Beach and Orleans Center. The...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    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 and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Updated, Spacious & Private, Sleeps 12 with Carriage House and Pool Peak Summer Weekly Rates:  $9,450 - $10,500 Rents Saturday to Saturday in peak season Linens Included   NEW Listing for 2018! A short stroll from a saltwater landing on Nauset Inlet you'll discover this vacation treasure in...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Home sleeps 14 close to Nauset Beach 2018 Season, NAUSET BEACH only 2/10 of a mile away! Nestled at the end of a gravel cul-de sac, this well-loved home is ready to become the canvas for new Cape Cod memories. 6 Rabbit Run was designed for entertaining & accommodating family & friends. The Great...
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    Orleans, Cape Cod 02643
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    First floor master suite and fully equipped separate guest suite make this newer custom Cape an ideal property for two families. The spacious design and top quality appointments in this builders own home assure you a comfortable, relaxing, and memorable vacation you'll truly enjoy. Granite...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    This exceptional compound is one-of-a-kind with a Main House, Carriage House and private pool. The Main house has a restaurant quality kitchen which will bring out the Iron Chef in you. Ample seating in the dining area with separate bar. Entertaining is easy in the Living Room with HDTV and DVD, it...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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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: $8,000-$8,500 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 first thing you'll...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    New to the Rental Market for Summer 2018. Large 4 bedroom, 5 bath home sleeps 14. Perfect for 2 families! First floor has a large open living room with TV, master with king bed and own bath, plus bedroom #2 with twin bunk beds. There is a second full bath off the kitchen area. Second floor has...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Waterfront Retreat with Scenic Water Views of Woods Cove, and Nauset Beach in Orleans to the Coast Guard Station in Eastham. This lovely contemporary 5 bedroom, 4 bath, 3 level home is set on a private and environmentally beautiful spot in Orleans. Launch your kayak at the water's edge. The first...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    Reviewed February 7, 2018
    The house is in a truly idyllic and very private setting. From the deck you overlook the gorgeous lake. When the mood strikes it’s a 30 second walk down to private access for...
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    A FEW PAST REVIEWS: 'The beach area behind the house was heaven sent, it's private, beautiful and easy. We also drove to the ocean which was about 5 minutes away. But we stayed at the house most of the time and had everything we wanted.' 2017 guest 'The house is in a truly idyllic and very private...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    On the Waterfront of Nauset Heights1 / 43
    (1)Excellent
    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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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    2013 WATERFRONT HOME! Gorgeous 3-level contemporary home with 180 degree view of a beautiful 28-acre lake and conservation lands. With water views from every room, this dramatic home has 3 exterior decks and a private path to the pond only 75 feet away. Set on a cul-de-sac on a private lane, it is...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Fabulous home Near Town Cove. 4 bedroom 3.5 bath home in Orleans. Professionally landscaped grounds. Outdoor shower off private patio. Gourmet kitchen with gas cook top and large island with counter seating...even a flat screen tv to watch while you are cooking or eating your breakfast! Well...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    3 BR | 3.5 BA | Sleeps 8 Built by the present owner's grandfather in the 1930's, this home is as close to the water as you can get. All rooms have views of beautiful Pleasant Bay. The ground floor boasts a new, fully-equipped, kitchen, a guest half bath, a large living room, a den/breakfast nook, a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    East Orleans; magnificent updated historic home, heated pool, A/C, perfect family vacation; Sleeps 13 Peak Summer Weekly Rates: $9,500 - $12,000 Rents Saturday - Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home   The interior of this beautiful 1920...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    5-BR Beach House Directly On Nauset Beach, Best Views on the East Coast Peak Summer Weekly Rate: $7,500-$7,900 Rents Saturday to Saturday Linens included NEW Listing for 2018! Perched on the dunes overlooking the open Atlantic you'll find this stunning beach house with easy access to Nauset...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    63 Briar Spring Road in East Orleans (ID #18264) ~ Waterfront Three Bedroom Home ~ Pochet Inlet Area 2018 Season Wonderful views! This updated home overlooks beautiful Pochet Inlet. Newly built in 2014, this property offers a spacious and open LR/DR/KIT located on the second level with a bonus room...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    This 4 bedroom, 3 and a half bath rental sits in a quiet area of Orleans. It is a quarter mile to Pah Wah Landing Conservation area on Little Pleasant Bay and a short walk through the conservation area to the beach. Little Pleasant Bay has great kayaking and boating from nearby Portanimicut Launch...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    This spacious home has it all - spectacular water views from almost every room. Just a short walk to Nauset Beach and multiple decks to enjoy ocean views! The house is well equipped and furnished and offers great living space for a family vacation. With 5 bedrooms and 3.5 baths, this spacious home...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 9
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Open updated home only 1/10th of a mile to The River that leads out to Pleasant BAY 2018 Season! Great Cape Escape Vacation Home sitting on 1.53 acre lot offers privacy in East Orleans! This bright, open contemporary home located in the exclusive Jack Knife Point Association offers peeks of the...
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    Orleans, Cape Cod 06543
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Path to Skaket Beach1 / 41
    (3)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Contemporary home with private setting just 3/10 mile walk through a private neighborhood association path to Skaket Beach. Back yard overlooks an active cranberry bog! Near the Cape Cod Bike Trail and less than a mile to Rock Harbor fishing fleet. There are 3 decks and a fully screened porch with...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    Superb Pleasant Bay Views, from Large, Luxurious, Secluded Orleans Vacation Home. Peak Summer Weekly Rates: $4,850 - $6,250 Rents Saturday to Saturday during peak season Linens Included Please click on the 'Virtual Tour' to see a 3D tour of the home Nestled in the woods of South Orleans on...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    This is a lovely, beautifully furnished 4 bedroom, 3 bath East Orleans property just 500 yards away from Mill Pond Landing and only 2.5 miles from Nauset Beach. It features a well equipped, efficient kitchen for entertaining, a formal dining area, a den with large panel TV, and a comfortable...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    15 Mill Pond Road, East Orleans, MA ID# 18164 ~ Mill Pond Area 2018 Season! Beautifully decorated home in the desirable Mill Pond area and with central air!. This comfortable home has an updated ktichen with new appliances, countertops, and flooring. Gorgeous Great Room with Cathedral Ceiling and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Washer
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Parking
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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