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South Orleans Rentals

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1,025 Houses

Topside MainHouse

South Orleans house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,227

Topside BoatHouse on Pleasant Bay

South Orleans boathouse

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$492

9 Woodridge Road 99912

South Orleans house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$186

52 Forest Way 18423

South Orleans house

5 bedrooms / 2 bathrooms / sleeps 8

“We enjoyed our rental very much.” This was the second year at this house. We enjoyed the house very much. It was clean and very well equiped. It met our needs, as a family, very well. There was plenty of room for all us. We have been coming to Cape Cod for a very long time and feel this is one of the best rentals we have had.

Price per night from

$200

Great rentals within 20 miles that match your search

Charming Cape Cod Cabin

Eastham house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$234

61 Chase Ave

Dennis Port apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$257

Sea Haven at Lecount Hollow Beach. Ocean View, 185 steps to the beach

Wellfleet cottage

2 bedrooms / 1 bathroom / sleeps 6

“A Great Retreat for a Beach Loving Family” Beautiful sunset and beautiful sunrise! Coffee on the beach in the morning! Good times boogie boarding on the atlantic breaks! Fun dinners on the back deck with ocean view. Comfortable for four adults! Armand was always just a phone call away when we needed him, like when we locked the keys in the cottage, he got us back in within minutes!

Responds fast! avg. 1 hour 51 minutes

Price per night from

$224

Surf Side cottage #3 at Surf Side Cottages. Walk to ocean beach

Wellfleet cottage

3 bedrooms / 1 bathroom / sleeps 6

“Love Surfside” Great service armand! Looking forward to return. Hopefully chimney works better.

Responds fast! avg. 1 hour 51 minutes

Price per night from

$237

Carpe Diem 4-bedrooms, ocean views

Wellfleet house

4 bedrooms / 2 bathrooms / sleeps 8

“Fabulous family stay!” We are a family of seven. This location and vacation house was perfect in all ways. We set up vollyball on the beach, went for fantastic walks, used the nearby bike paths, visited other beaches, went into town, and swam in the kettle ponds close by. Great times for our family. We will be doing this again next Summer. Loved it!!

Responds fast! avg. 1 hour 51 minutes

Price per night from

$1,096

Bessies Cottage - Lower priced alternative

Wellfleet cottage

2 bedrooms / 1 bathroom / sleeps 4

“Good Value-Nice small house” Great alternative to a hotel at reasonable price. Has wifi, tv and even a/c in the bedrooms. Nice back deck, with bike trail right behind. Has everything you need (very thoughtful). (Could use a bit more lighting.) Just off rt 6 on side-street, so can be a bit noisy if you want absolute quiet but very convenient location. And armand is a prince! Nice master BR with another small room with bunk beds.

Responds fast! avg. 1 hour 51 minutes

Price per night from

$131

Cliffside Cottage at Surf Side. Just down the street from a great ocean beach.

Wellfleet cottage

3 bedrooms / 1 bathroom / sleeps 6

“Life is Good!” Cliffside allows you to slow down and enjoy the little things that make life special. This was our second stay at Cliffside and we hope there will be many others. We love this cottage. Wonderful kitchen with delightful yellow dishes, comfy beds, cozy decor, lots of light via all the windows and skylights, fireplace for chilly evenings and an extra shower outdoors for sandy toes. Didn't use the available internet and glad there is no tv. Lots of family games and books to enjoy! Great little walk to the beach. The multitude of songbirds in the pines surrounding the cottage will make sure you don't miss the sun rising over the ocean. Location is close to everything on the Cape. Spending time away from Cliffside can be difficult though. A second coffee in the screened in porch makes you want to linger all day. Armand and Lisa make you feel right at home when you arrive and are always happy to recommend local restaurants, provide assistance and ensure your stay is perfect in every way. East coast hospitality at it's very best! If you want to step away from the hurried pace of everyday life, then Cliffside is the place to relax!

Responds fast! avg. 1 hour 51 minutes

Price per night from

$195

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.

Price per night from

$229

One of a Kind " The Nauset Teepee" Oasis near the bay, now w/NEW A/C!!!

North Eastham house

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$287

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.

Price per night from

$344

“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 56 minutes

Price per night from

$315

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

$733

Beautiful Home - Great Price, Wi Fi, Flat Screen

Yarmouth house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$144

Beachcomber at Surf Side 200 steps to a wonderful ocean beach

Wellfleet cottage

2 bedrooms / 1 bathroom / sleeps 4

“Home away from home- and the best beach ever!” Steps away from the sand and surf, this cottage was right next to one of the best beaches in the us. The manager was incredibly helpful, welcoming and friendly, we felt very much at home. The bathroom was rather small (not that big of an issue), the beds could have been more comfortable, but the kitchen was great, all of the amenities we could have wanted to make our stay super convenient. This cottage is in a great location, if you can pull yourself away from the beach there are a number of stunning biking and walking trails, and of course a great French bakery up the street!

Responds fast! avg. 1 hour 51 minutes

Price per night from

$208

Ocean Breeze Cottage at Surf Side 200 steps from the ocean beach

Wellfleet cottage

2 bedrooms / 1 bathroom / sleeps 4

“A little bit heaven away from the everyday world!” We had a wonderful time at Ocean Breeze! Armand and Lisa are great hosts. Armand met us at the cottage and provided helpful information about all the interesting local attractions. The cottage was clean, quaint, and peaceful. The sound of the wind, surf and birds was incredibly soothing. The location was perfect too. The cottage is steps from LeCount Hollow Beach and close to the Cape Cod Bike Trail. Several historic town centers are nearby which off a wide variety of excellent shopping, art galleries and dining experiences. We enjoyed everything from the fresh seafood (blue fish is delicious) to the early morning walks on the beach (LeCount Hollow is great for Grey seals, tidal pools and polished glacial rocks and pebbles). Roasting marshmallows and observing the stars, moon and the Milky Way on clear nights is quite a treat as well. A perfect vacation- Ocean Breeze is a fantastic vacation spot on the Cape!

Responds fast! avg. 1 hour 51 minutes

Price per night from

$201

Ocean View Cottage at Surf Side - Roof-top Deck. Walk to ocean beach

Wellfleet cottage

3 bedrooms / 1 bathroom / sleeps 6

“Fantastic stay with great management!” The service was fantastic. Management was very attentive and knew all of the best places to go and events to experience. The home was very cozy, clean and located very near the beach. We were right inside the boundaries of the Cape Cod National Sea Shore, which meant that we were close to amenities and yet isolated enough to be comfortable and not crowded. The management service and location was what we liked best, with access to the beach and access to excellent information. Unfortunately, the weather during our stay was mainly cloudy and cold. But, you can't control the weather! We look forward to next years return trip and hope for sun!

Responds fast! avg. 1 hour 51 minutes

Price per night from

$208

Oceanside Cottage at Surf Side - Roof-top Deck - Walk to ocean beach

Wellfleet cottage

3 bedrooms / 1 bathroom / sleeps 6

“A Very Relaxing Time by the Ocean” We stayed in the Ocean Side cottage for one week in the off season and found it very relaxing. We walked along the ocean for many hours, cooked some awesome meals using seafood from the local fish market and read books. The cottage is very nice. It has a late 1940/early 1950 feel with knotty pine paneling throughout. The owners are quite artistic and have adorned the place with paintings and drawings and funky things. The kitchen is modern and ready for cooking, yum, yum. The screened in porch is a very nice place to sit and it is very quiet. The national seashore is across the street and through the dunes. Being so close to the beach you can go there night or day. Watching the moon rise over the atlantic was wonderful. Also, it is dark enough to see a billion stars. We are looking forward to returning to the same cottage next year. Can't wait!

Responds fast! avg. 1 hour 51 minutes

Price per night from

$237

Sea Breeze Cottage at Surf Side Walk to ocean beach in National Seashore

Wellfleet cottage

3 bedrooms / 1 bathroom / sleeps 6

“An indoor cottage with an outdoor feel” Armand was right on getting with us and making sure we were settled! Since we've vacationed in this colonie, we knew what to expect...having said that though, the outdoor shower was definitely our favorite part. At the right time of the morning, the sun shone directly into the shower and warmed us more than the water! The only thing that was tricky for us was setting up the dinner table every night...heavy and no wheels to make the job lighter. We understand the need for the hide-away table, though.

Responds fast! avg. 1 hour 51 minutes

Price per night from

$208

Bonnie Dune at Surf Side Walk to ocean beach

Wellfleet cottage

3 bedrooms / 1 bathroom / sleeps 6

“Charming , delightful place.” Armand was always available, kind and helpful. The house is situated in a lovely place and the beach is only a few minutes away. We had all what was necessary for a comfortable stay and we liked everything about this cottage . Our dog enjoyed the place and felt right away at home. Within minutes distance there is an excellent French Bakery. All the details about what this cottage is offering are clearly presented on their website. This is a charming place and will go back as soon as we can.

Responds fast! avg. 1 hour 51 minutes

Price per night from

$212

Surf Rider Cottage at Surf Side - Roof-top Deck - Walk to ocean beach

Wellfleet cottage

3 bedrooms / 1 bathroom / sleeps 6

“Happy Families” We found out about these cottages via Travel and Leisure Magazine. Everything was as described- so yes, a little basic on the amenities, but we knew that. We had a wonderful time, and photographs and memories will keep us thinking of our trip. Armand and Lisa were great to deal with, and we enjoyed the quiet beauty of Lecount Hollow beach, and the more boisterous beach bar scene at the Beachcomber.

Responds fast! avg. 1 hour 51 minutes

Price per night from

$208

Price per night from

$287

Black Fish Creek, Reasonably priced charm, comfortable cottage

Wellfleet cottage

2 bedrooms / 1 bathroom / sleeps 5

“Wonderful Stay!” I had the opportunity to stay at the Black Fish Creek cottage recently with my dog and boyfriend. We loved the cozy cottage and it provided us with all that we needed and exceeded our expectations. It is set off the road so my dog was able to be off-leash, which she loved. The cottage itself is very quaint with beautiful hard wood floors, lots of windows and light and open floor plan. The location is close to Marconi beach and a fabulous French Boulangerie. We received friendly and helpful service from Surfside Cottages and we hope to return and I will recommend to friends and family.

Responds fast! avg. 1 hour 51 minutes

Price per night from

$161

Silver Sands Cottage at Surf Side

Wellfleet cottage

2 bedrooms / 1 bathroom / sleeps 4

“Nice cottage, excellent location” Nice 2 bedroom cottage, very attractive inside. Be prepared for sand on the lot around the cottage - you're quite near the beach. Not extremely private since 4 other cottages are nearby, but a very adequate sized yard. Nice gas fireplace, outdoor fire pit and hammock.

Responds fast! avg. 1 hour 51 minutes

Price per night from

$208

Piney Ridge Cottage at Surf Side - Walk to ocean beach

Wellfleet cottage

3 bedrooms / 1 bathroom / sleeps 6

“The best vacation I ever had.” Wellfleet is just heaven. It is friendly and down to earth. There is more to do than one is able. Every outside activity is available. Just about every entertainment is there as well, much of it at no cost. We biked, hiked, jumped waves, minigolfed, saw indoor and outdoor theatre and more. The cottage was perfect. It is simple and clean. Steps away from the beach. A short walk from three wonderful bakeries. Lots of great dining and farmer's market options. It is just off the main road so very quiet. We walked back to the beach each night to view the stars. A perfect cottage and a fabulous vacation.

Responds fast! avg. 1 hour 51 minutes

Price per night from

$206

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.

Responds fast! avg. 47 minutes

Price per night from

$264

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. 41 minutes

Price per night from

$229

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

Price per night from

$144

Spectacular Waterfront Townhome - Oyster Pond #25

Chatham house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 34 minutes

Price per night from

$871

Summer Fun in Eastham

Eastham cottage

/ 1 bathroom / sleeps 2

Price per night from

$115

Vacation Home Away from Home!

Truro house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$295

Walk to Beach, Beautiful Brewster Home! Crosby

Brewster house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 26 minutes

Price per night from

$613

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!!

Responds fast! avg. 3 hours 28 minutes

Price per night from

$573

High-end Brewster ,Mass. Bay view town home

Brewster apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$409

Wellfleet Cottage on the bay

Wellfleet apartment

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$303

Viewing 38 of 1,025
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