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Orleans Holiday Rentals

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    Travellers to Orleans are booking July dates now. Secure your holiday rental today, and have the perfect trip.
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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
    Newly Listed and Newly Updated, this is the rental you’ve been looking for!! Situated in a secluded wooded neighborhood, not far from shops and restaurants. Perfect home base, just 1.7 miles from popular Skaket Beach on Cape Cod Bay, 1 mile from Rock Harbor sunsets, and the bike path is just .3...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 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, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    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 property to the water. You won't find another rental like this...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Price $3195 SKAKET BEACH is just 3/10th's of a mile away via path at Willie Atwood Rd and Cape Cod Rail Bike trail access is very close to this splendid Orleans home! This 4 bedroom home with Central A/C is set on almost an acre of land down a sand lane, steps from Cape Cod Bay and the Cape Cod...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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”...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Grill
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    • Hot Tub
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    • Private Outdoor Pool (Unheated)
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    About this property
    Private Orleans resort-style compound with heated pool & spa, fire pit and cabana (linens included) NEW Listing for 2017! (more photos to come as renovations are completed) Peak Summer Weekly Rates: $12,500 - $14,000 (Rents from Sunday to Sunday during peak weeks) Your multi-generational or...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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...
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    Orleans, Cape Cod
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Price Range $1895-$2245 Situated between Skaket Beach on the bay and Nauset Beach on the ocean, this beautifully renovated home is tucked in a quiet neighborhood. It is a short walk to playgrounds, public tennis courts, the town of Orleans for great shopping and dining to satisfy every palate, and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Three bedroom with A/C * Wireless Internet * NO Pets Accepted 2017 Season! Located on a quiet street in a private setting this 3 bedroom, 3 bath tri-level home is just 1/2 mile to Rock Harbor & a short drive to Skaket Beach and the local shops and restaurants in Orleans! There is an AC unit in...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cape Cod ~Cozy  Relaxing Vacation Apt.1 / 6
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 27 August 2015
    Had a wonderful week with our family at this beautiful apartment. It is exactly like the photos! Clean, quiet and relaxing! Would definitely return! The owners live on the...
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    About this property
    Lovely Summer Rental in East Orleans. Approximently 0.5 miles from Nauset Beach. This apartment will sleep 4. One seperate bedroom with queen bed. Bathroom and shower. Murphy bed available.in sitting area. Comfortable sitting area with Direct TV, WiFi, washer and dryer, microwave among the...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Bright and spacious ranch located on a wonderful, 1.2 acre level lot off a quiet lane the desirable Barley Neck area of East Orleans. With A/C units in the living area, loft and bedrooms, and brand new finishes and furnishings throughout! Two bedrooms are on the main floor, each with a Queen bed...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 BR Waterfront Condo on Cape Cod Bay at Skaket Beach, Orleans MA1 / 28
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    About this property
    My Cape Cod waterfront vacation rental is located on the very popular Skaket Beach in the town of Orleans and has been enjoyed by thousands of vacationers for over 5 decades. I have been blessed to be the owner for over 30 years. You’ll enjoy 250 feet of private Skaket Beach with only 7 other...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    15 Mill Pond Road, East Orleans, MA ID# 18164 ~ Mill Pond Area 2017 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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    • Washer
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    26 Winslow Drive, Orleans (ID# 18543) ~ South Orleans 2017 season ! Located in South Orleans and close to Chatham for shopping and dining! This home is less than ½ mile to the beaches on Pleasant Bay and overlooks scenic Uncle Seth’s Pond. This contemporary home with an abundance of glass offers...
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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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    • Satellite TV
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    Spacious Orleans Home on Crystal Lake Includes Linens and Beach with Kayaks, Canoe & SUP Boards! Peak Summer Weekly Rates: $5,400 (Rents Saturday - Saturday during peak season) This expansive waterfront home is located on Crystal Lake in the heart of Orleans. Kayaks, a canoe and stand-up paddle...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    244 Tonset Road, East Orleans (ID#125800) Reduced rate for the week of 8/12-8/19! 2017 Season! Adorable vacation rental located in East Orleans. This property has a screened porch overlooking the private back yard located in a nice neighborhood equidistant to Nauset Beach on the Atlantic Ocean and...
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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 6 Quick View
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    This charming Cape sits on a large lot on a quiet street in Orleans. This is a great location with easy access to Skaket Beach, the Rail Trail for biking and also easy access to shops and restaurants. The deck overlooking a large yard is a great place to relax and unwind at the end of a busy day at...
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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 10 Quick View
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    27 Pond Road, Orleans (ID# 22347) 2017 Season! Nestled on a private 1.5-acre wooded lot, this charming and newly constructed home combine’s comfort with gracious living! The large kitchen features high-end appliances, marble counters, breakfast booth with bay windows and opens to the dining area...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lovely three bedroom contemporary Cape with an open floor plan located in a private cul de sac neighborhood. Features wireless internet, deck and private outdoor shower and is near the bike trail. Two bedrooms are on the first floor. One with a trundle bed and the other with two twins. Upstairs...
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    Orleans, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Step back in time in this classic turn of the century cottage with views of Cape Cod Bay. Located on a wonderful property with an expansive yard, a screened-in porch and a path down to the sandy shore of Cape Cod Bay. Additional amenities include: beach chairs, crock pot, room fans, lobster pot,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Just a short distance to the center of Orleans, this well kept Saltbox style house is convenient to everything. It is only .3 miles to the bike path and 1.6 miles to Skaket Beach. The large grassy yard is private and spacious. The cute back deck comes equipped with an electric grill and outdoor...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 7 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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    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...
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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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    This Orleans property features stunning views of Robert's Cove from almost every room in the house. This custom built home has a casual floor plan that takes advantage of the serene waterfront setting, as well as comfortable furniture for relaxing. Enjoy the pathway around Robert's Cove or bring...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    This immaculate home is located in a quiet neighborhood with just a .2 mile walk down a sandy path to Skaket Beach. It is also close to the bike trail and nearby shopping and restaurants. The home features an open floor plan with skylites, a spacious screened porch with seating, and a large back...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Price Range $1745 NEW LISTING! BOOK BEFORE JULY 4TH AND SAVE $74 OFF THE WEEKLY RATE!! THAT'S ONLY $1665 TOTAL FOR A COTTAGE BY THE SEA!! This idyllic 3 bedroom/1 bath home sits at the end of a quiet cul-de-sac. A down to the studs renovation was designed to maximize space and sunlight. Its...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Recently renovated home tucked up on a knoll located in a very pleasant East Orleans neighborhood. The addition of a new second floor consists of two spacious bedrooms that look out to a scenic pond across the way and a nice bath. The rest of the home offers comfortable furnishings with all...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    25 B Doane Road, East Orleans (ID# 106441) Nauset Heights 2017 Season! Adorable 2 bedroom cottage in Nauset Heights. Peeks of Mill Pond and around the corner from the landing. Cute, clean and charming 2 bedroom, 1 bath cottage with central air conditioning, part of the Pilgrim Lane cottages....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Spotless home in a lovely quiet setting near the bike path. There are two living spaces and a first floor laundry and half bath. The first floor bedroom has a queen size bed. On the second floor there are two bedrooms with a queen bed and two twin beds and a full bath. Large two level deck. There...
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    Orleans, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Smoking allowed
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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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    This recently renovated 2 bedroom,1 bath cottage is nicely appointed in a prime East Orleans location, convenient to beaches and shopping. It is situated across the street from Town Cove and Asa's Landing and offers views of the water. The cottage has lovely grounds and gardens to enjoy, as well as...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    • Private Outdoor Pool (Heated)
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Lovely expansive home with pool and privacy near Crystal Lake and Kents Point.58 Keziahs Lane . 2017 Season! Located in the Town of Orleans, Fields Cove" Beautiful Peaceful Setting of this 6000 sq.ft.expansive home enjoying enchanting water views out over the 38 x 16 in-ground heated pool out to...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
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    20 Hayward Lane, East Orleans (ID# 108991) Close to Nauset Beach MeetingHouse Pond, Pleasant Bay and Village of East Orleans 2017 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, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Set on a rise in a quiet South Orleans neighborhood, this single-level home offers plenty of privacy and living space: a living room opening to the backyard deck, a dining room, kitchen breakfast bar, and a family room leading to a sunroom that also opens to the backyard deck. Ductless A/C,...
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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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    Smoking allowed
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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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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
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    • Satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Price $2075 Lovely Cape Cod Vacation Bungalow located in Orleans. The perfect Cape retreat near Skaket Beach and less than .5 mile to Orleans Town Center and Rock Harbor! The bright, nautical-themed living room features a flat screen TV, DVD player, and a sleeper sofa. The kitchen if fully equipped...
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    Orleans, Cape Cod 2653
    Cabin Holiday Rental - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
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    36 Collins Lane, East Orleans (ID# 114103) Gorgeous 5 bedroom home with Central A/C and all the amenities. First floor features a luxury eat in kitchen with granite countertops and stainless appliances, great dining room, and living area with gas fireplace. First floor bedrooms include a spacious...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    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...
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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 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great privacy in East Orleans! Enjoy this lovely 3-bedroom, 2-bath contemporary saltbox offering a bright and open floor plan and updated furnishings. Front-to-back living room with fireplace and a great screened porch open onto a spacious wraparound deck. This great vacation spot is gracefully...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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