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South Orleans Rentals

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1,111 Houses

Topside MainHouse

South Orleans house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,209

Topside BoatHouse on Pleasant Bay

South Orleans boathouse

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$484

9 Woodridge Road 99912

South Orleans house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$186

17729: Newly Renovated, Across from Round Cove on Pleasant Bay, Next Door to Weq

South Orleans house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$99

18824: Beautiful Home in Fantastic Location Close to Pleasant Bay & Chatham/Orle

South Orleans house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$83

17733: Immaculate Home + Fantastic Location - Walk to Jackknife Beach, Wequasset

South Orleans house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$148

Great rentals within 20 miles that match your search

Central air conditioning, New House - Bayside Close to Campground Beach

Eastham house

4 bedrooms / 3 bathrooms / sleeps 8

“A great family vacation!” This was a great house! The sleeping accomodations were perfect for my family. The house had everything we needed and the location was ideal for staying in Eastham. The bike path had several entrances near the home and being pm the bay side of the cape allowed my wife and I to relax on the beach even with small children. Having a screened in porch too was a huge benefit of the house. Nice to have dinner outside without being dinner for the local Mosquitos.

Responds fast! avg. 1 hour 36 minutes

Price per night from

$226

Central air conditioning, New Eastham House - Steps to Beach

Eastham house

4 bedrooms / 3 bathrooms / sleeps 8

“Great comfortable beach house” My wife and 2 children & I have been staying at this house for 7+ years, and it is a close walk of approximately 600 yards to a great Bay beach. This allows you to easily return for lunch. The house is comfortable for 2 families, as we always have another family of 4 visit us there. The beach is ideal for young children, and the house has all of the amenities of home. We look forward to another Summer Vacation in 2011.

Responds fast! avg. 1 hour 36 minutes

Price per night from

$339

“Great time!!” This wonderful home was great for our Cape vacation! The home is beautiful and the owner's pride and love for their home shows throughout the property. The owners were excellent to work with, very professional and very responsive to inquiries. The house is beautifully decorated and extremely well stocked with everything we needed to make our vacation perfect. We appreciated all the amenities - inside and out, the huge rear deck was one of our favorite places to relax and enjoy the quiet area and the beautiful landscaping, we could even hear the waves at night. The location was very convenient to restaurants, shops and beaches and is centrally located to exploring anywhere on the Cape. We are looking forward to calling this our "home away from home" again!!!

Responds fast! avg. 1 hour 42 minutes

Price per night from

$311

Olde Sea Captains House great for family reunions. 7/10th of a mile to the beach

Dennis Port house

6 bedrooms / 4 bathrooms / sleeps 16

Price per night from

$723

Beautiful Home - Great Price, Wi Fi, Flat Screen

Yarmouth house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$170

Cape Cod 2 BD cottage (June $1200wk) private beach in W. Hyannisport

West Hyannisport house

2 bedrooms / 2 bathrooms / sleeps 4

“Our family enjoyed a memorable reunion week in this beach neighb” We spent the week walking to aves, swimming at Squaw Island, golfing, tennis, and dining out at some great restaurants. This beach house has central air, a new gas grill and outdoor shower. All musts for our vacation rental requests. Nice quiet area with great Cape Cod experiences. The house is clean and comfortable. Great master bed. Near boats to the vineyard and Nantucket. We plan on another family reunion vacation at this beach house again this summer.

Price per night from

$260

Dennis Port walk to beach!

Dennis Port house

3 bedrooms / 1 bathroom / sleeps 7

“Relaxing..near the beach and centrally located” We truly enjoyed this cozy cottage...The beach was s short walk away and restaurants and shopping plazas where nearby. Getting to all parts of the cape was easy. We would definitely rent again.

Responds fast! avg. 1 hour 13 minutes

Price per night from

$282

Classic Cape Cod cottage on a quiet lane

Eastham cottage

2 bedrooms / 2 bathrooms / sleeps 4

“Perfect location” We had a wonderful time on vacation in this house. It was spacious and sunny and the yard was huge. Location was perfect walking distance to bay beach and fresh water pond. Also close driving to all of the fun in Eastham. The owners were super helpful with all my questions....and I often repeated questions and asked a lot. Thanks for a great vacation. Sharon

Responds fast! avg. 2 hours 56 minutes

Price per night from

$146

Spectacular Waterfront Townhome - Oyster Pond #25

Chatham house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 46 minutes

Price per night from

$859

Summer Fun in Eastham

Eastham cottage

/ 1 bathroom / sleeps 2

Price per night from

$113

Vacation Home Away from Home!

Truro house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$290

Walk to Beach, Beautiful Brewster Home! Crosby

Brewster house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 18 minutes

Price per night from

$604

Beautiful sunsets in Chatham!

Chatham house

4 bedrooms / 3 bathrooms / sleeps 8

“Wonderful vacation home in great location, a cooks delight!!” Our family could not have been happier spending our vacation in the wonderful Chatham home. The kitchen is fully equipped and great room for family to congregate. The sunset on the pond was spectacular and owners were so pleasant to deal with. They were extremely accommodating. Great location for enjoying all cape beaches, hopping on the bike trails and enjoying Downtown Chatham. I would highly recommend!!

Price per night from

$565

High-end Brewster ,Mass. Bay view town home

Brewster apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$403

Wellfleet Cottage on the bay

Wellfleet apartment

3 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 49 minutes

Price per night from

$298

CapeCod nrOcean quiet woods ac Sleeps12, dsl

Truro house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 1 hour 52 minutes

Price per night from

$967

The Cape Cod Cottage with Beach Pass

Eastham cottage

3 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 35 minutes

Price per night from

$290

MID CAPE Harwich Cape Cod Rail Trail access 300 f Minutes to Ocean/Bay beaches

Harwich house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 55 minutes

Price per night from

$234

“Great cottage just steps from the beach” We stayed at the cottage for a week with our two children and my parents. The house has recently been updated with a new porch and interior renovations. This is a charming little cottage with a great outdoor space and nice landscaping. You feel like you can just sit there all day and soak in the rays. The robust porch is accompanied by a cozy sunroom that provides just enough privacy for you workaholics who can't shut off your laptop (I am not speaking from experience...). The gas grill is stocked with propane, there is a great outdoor shower, the kids ran upstairs to find a room with some stuffed animals, there were games, movies, books and the view from the upstairs bedroom on the left might be one of the best on the cape. Needless to say, we will definitely be going back. If you are lucky, Charles will catch you before you leave. Very nice guy, and a great property owner.

Responds fast! avg. 1 hour 55 minutes

Price per night from

$597

Serene Pond Setting

Truro cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$290

Quiet and comfortable 3 bedroom cape

Eastham house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$322

Minute Walk to Beach and Downtown Harwichport

Harwich Port house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$339

Cape Cod Home w/Ocean View, Walk to beach; 3 baths

South Harwich house

4 bedrooms / 3 bathrooms / sleeps 10

“Wonderful!!!” The house was great. The owner was very easy to deal with and everything was done over the Internet with no problems. Located in beautiful South Harwich with the ocean nearby and the towns of Chatham and Harwichport only minutes away. If you are looking for a great place to have a worry free vacation, I strongly recommend this house

Price per night from

$1,129

Classic, Quiet, Private Dennisport Cottage

Dennis Port cottage

2 bedrooms / 1 bathroom / sleeps 4

“Perfect Cape Cod Vacation Cottage” We just returned from our week-long stay at this beautiful, immaculately clean cottage. We fell in love with it online, and it certainly did not disappoint! I can honestly say that there was not one thing lacking from this home. Everything we needed was included; just bring some food and a bathing suit and have a great time! The cottage was the perfect size for our family of four, and the family and friends that joined us on the beach for a day all loved the coziness and décor as much as we did. The ocean is a short walk away, but we bought a parking pass for the week, and were happy that we did. Although we did not explore as many different beaches as we thought we might, it was so convenient to have the pass and be able to pack all our things in the car, drive down to Inman Beach, and have the option to make quick (5 minute) trips back to the house for extra drinks/snacks, bathroom breaks, etc. Parking was never an issue at Inman, so there was no concern about losing a spot. Also, don’t miss out on picking up some steamers from George’s Fish Market. We ate them on the back deck after long days on the beach – perfect and delicious! We can’t wait to return next summer, thank you Lynn and Mark for sharing your home with us!

Price per night from

$226

Former Chatham Bed and Breakfast

Chatham b&b

6 bedrooms / 5 bathrooms / sleeps 12

“Classic cape cod experience” Beautiful property well located on the cape non commercial sector. Tastefully appointed overall fantastic.

Price per night from

$629

Unique & Private 3 Bedroom Brewster Home

Brewster house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$323

Cape Cod Luxury Oceanfront 5bdrm Vacation Home

Chatham house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$968

Luxury Home - Steps to Sandy Beach

South Yarmouth house

4 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$1,613

Cape Cod Cottage, 4 bedrooms, 2 baths, Eastham, MA

Eastham cottage

4 bedrooms / 2 bathrooms / sleeps 10

“Great Cottage” I spent a weekend in this cottage and had an overall excellent experience. It is in a great location and is within a close trip to the beach. The cottage was clean, comfortable, and has enough rooms and beds for many people. I will definitely come back next time I am in the Cape.

Price per night from

$328

Hedgebound of Cape Cod

Truro house

8 bedrooms / 6 bathrooms / sleeps 20

Price per night from

$3,385

Walk to Beach; 4 bedroom, 4 ba, Cape Cod Farmhouse

West Harwich house

5 bedrooms / 4 bathrooms / sleeps 8

“Delightful” From beginning to end, this was the absolute perfect place to stay on our Cape Cod adventure. The house was about as charming as you could get. We had 12 of us amazingly fit, with the rooms being so spacious. There were nooks and crannies with the cutest little details, book shelves for readers, games, a wonderful outdoor shower... Cindy and Harry have really put some thought and loving care into maintaining this beautiful house. We had family staying at several other locations and every night they all ended up here, usually around the fire pit. It's just a warm and friendly place to be. I must mention the 2 sheep that were on the property... adorable!! A nice walk to the beach and stores but really, at the end of the day, we just loved hanging out at the house.

Price per night from

$677

Spectacular Waterfront Home - Oyster Pond 31&32

Chatham house

4 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 46 minutes

Price per night from

$1,071

Viewing 38 of 1,111
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