House holiday rentals in Osterville, Barnstable

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Popular amenities for house rentals in Osterville, Barnstable

House rentals with a pool

Superhost
Home in Chatham
4.95 out of 5 average rating, 21 reviews

Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

JudyRating, 5 stars2 days ago
James was very responsive to several problems we had with the property. He immediately asked if we wanted him to come out to fix the issue. All in all, it is a wonderful place, perfect for a family reunion! The downstairs space is perfect for kids to watch TV and play games. We expect to rent this property again! Thank you
Top guest favourite
Home in East Sandwich
5 out of 5 average rating, 31 reviews

XL Estate: 2 Homes-Pool-Tennis-Game Barn - 20 ppl

BobRating, 5 stars1 month ago
Joshua's place was the PERFECT place for our dad's 70th birthday! The 9 kids had an amazing time between the pool and game barn there was constant entertainment for all ages! If you have a big family/group this is the spot!
Superhost
Home in Barnstable
4.76 out of 5 average rating, 21 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

KristenRating, 5 stars2 months ago
This house and property were charming and beautiful. The location was extremely close to beaches, restaurants, and stores all while being nestled in a quiet neighborhood. Highly recommend!
Top guest favourite
Home in Sandwich
4.99 out of 5 average rating, 83 reviews

"Cape Escape" luxury home w/pool & beach access.

Kimberly AnnRating, 5 starstoday
I can not say enough about how wonderful this house was to stay at for my son's wedding weekend. This house was very clean and organized. The hosts were extremely thoughtful with how everything was laid out. They thought of everything that you would need or might forget. The outdoor space was great!! My grandchildren and kids floated around the pool and played yard games. I did not hear "I am bored" and that was wonderful. We had so much space to get ready for the wedding and were able to get wonderful pictures of my son getting ready for his wedding. There are so many places in the house to either gather together or to go off and do something else. Two kids were playing chess while the younger ones were down playing with the video games and my dad and the men were watching the Masters. We had plenty of space for everyone to hang out. My entire family enjoyed this house and can't wait to go back.
Guest favourite
Home in Popponesset
5 out of 5 average rating, 13 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

CarolRating, 5 stars1 month ago
We loved are family stay at Paul & Katie’s home for Easter Week. It is a dream home . The neighborhood was beautiful and walkable, with a peaceful path to a private beach. We enjoyed the shops and restaurants in Mashpee Commons about an 8 minute drive away.
Guest favourite
Home in New Seabury
5 out of 5 average rating, 20 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

AriannaRating, 5 stars3 weeks ago
We had a wonderful stay here in New Seabury! The house is beautiful, spacious and just as described. The heated pool was an added bonus! Michael provided prompt and clear communication when needed. I would absolutely stay here again!
Superhost
Home in Chatham
5 out of 5 average rating, 4 reviews

*NEW* Pool. Hot Tub. Game Room. Beach Nearby!

JonRating, 5 stars2 weeks ago
Great house, plenty of areas for everyone to have their own space. college boys loved the games in he house when it was chilly, and also enjoyed outdoors, while parents had plenty of space and peace and quiet when needed. Dinner and watching sports on TV together was also easy, as space is really great. Lucia is as solid of a communicator as any host we've had, she was terrific and helpful. Of course, the Cape and Chatham is a terrific area to visit. Would definitely rent this house again and anything Lucia has.
Top guest favourite
Home in Hyannis Port
5 out of 5 average rating, 13 reviews

Home in Hyannis Port

Ryan & LindsayRating, 5 stars1 week ago
Our family of five had a wonderful stay! We picked the location because it was in the middle of the Cape and easy for us to explore the coast. The house is newly renovated and in pristine condition. The beds were comfortable and the bathrooms were fresh and new. We had plenty of space and felt right at home. The host was very responsive. We highly recommend!

Weekly house rentals

Guest favourite
Home in Barnstable
5 out of 5 average rating, 18 reviews

8 Min Drive to Beaches! Brand New, Bright, & Fresh

NatRating, 5 stars3 weeks ago
Exceeded our expectations! We had a wonderful stay at Priscilla’s place in Barnstable over Memorial Day weekend. We spent three nights there, and it had everything we needed. The neighborhood was quiet, the space was newly renovated, and the backyard was huge; perfect for our dog, Oxford, who loved every moment of yard playtime. We had the pleasure of meeting Priscilla, who was friendly and welcoming right from the start. Oxford enjoyed her company too—it was clear he liked her! We’ll definitely stay again.
Guest favourite
Home in Hyannis
4.95 out of 5 average rating, 19 reviews

Fully Renovated Cape Cod House, Fenced In Backyard

LisaRating, 5 stars2 months ago
It’s always wonderful when what you see in online photos is what you get when you open the front door! Yulia’s home is beautiful with all the comforts of home and conveniently located to the ferries to the islands. Its location allows you to bounce around to various spots on the cape, by car of course :)
Top guest favourite
Home in Barnstable
5 out of 5 average rating, 21 reviews

Hyannis Cape Escape

LaurenRating, 5 stars3 weeks ago
My friends and I stayed here for my bachelorette, and it was absolutely amazing! The hosts went above and beyond to make sure our stay was great and even left treats for us upon arrival. The house is stunning, clean, and in a wonderful area on the cape. Cannot recommend it enough!
Guest favourite
Home in Mashpee
5 out of 5 average rating, 9 reviews

Swan nest escape

VadimRating, 5 stars9 months ago
I had high expectations coming in, but this home exceeded them by far. The interior is spotless, the condition is great, you could see that the owners put a lot of effort into it with lots of nice little touches to improve utility and aesthetics. Eugeniya was super helpful the entire time, she and Rudy are awesome hosts. I want to point out that the location is also very nice. We liked the town, the restaurants, the beach (15-20 minutes drive), Mashpee Commons. Santuit pond is wonderful and provides some nice fishing spots. The big pleasant surprise was the Santuit Pond Reserve, it’s in walking distance and provides tons of great hiking opportunities. There are many other attractions nearby, I recommend visiting Heritage Museums & Gardens in Sandwich (20 minutes away). Overall we had the best time, I highly recommend this place!
Top guest favourite
Home in Barnstable
4.98 out of 5 average rating, 42 reviews

Private Lake Beach | Spectacular Views & Amenities

AndrewRating, 5 stars1 month ago
This is an absolutely beautiful rental and location. Cleanest, most pristine location we have been to. Appliances and bathrooms are glimmering. Host is immediately responsive and kind. 10 out of 10 in all respects.
Top guest favourite
Home in Centerville
5 out of 5 average rating, 69 reviews

1MILE TO BEACH* Central Location * BEACH PASS *

DAVIDRating, 5 stars9 months ago
Cindy’s home was meticulously kept and we thoroughly enjoyed our stay. It is very convenient to Hyannis Port which offers regularly scheduled ferries to Martha’s Vineyard and Nantucket. It was very easy to travel around to other spots on Cape Cod, including Chatham and Provincetown. Cindy was very communicative, as was particularly valuable when she informed me shortly after our departure that I had left my own home keys instead of the property keys; in time to catch us before we left the area. Phew! The home was well furnished and peaceful. Definitely a great place to spend your vacation.
Top guest favourite
Home in South Dennis
5 out of 5 average rating, 64 reviews

Beachfront· Sauna· Screened Patio· 2Kings· DogsYes

MichaelRating, 5 stars3 days ago
Amazing home. Fantastic location. Peaceful and relaxing. One of our favorite vacation stays ever. Never turned the tv on… unusual for me. Hosts really thought of everything and more. Highly recommend if you are visiting Cape COD. 5+ stars.
Top guest favourite
Home in Barnstable
5 out of 5 average rating, 49 reviews

Spacious 2k sqft, cozy & charming with Central Air

JaneRating, 5 stars3 weeks ago
Mary’s place is clean and spacious . Great for a get away weekend with a group of friends or family vacation. They have a family room on the 1st floor which is great for activities . They also have plenty chairs , tables , and couches in the common area . Neighborhood is very safe and quiet . Will stay again when we come to visit .

Private house rentals

Guest favourite
Home in Barnstable
5 out of 5 average rating, 56 reviews

*LAKE VIEWS* 0.2mi to Lake Wequaquet beach 4bd/2ba

KatarzynaRating, 5 stars3 weeks ago
We had a wonderful stay at this beautiful home! Allison was incredibly accommodating, which made settling in easy and stress-free. The house is thoughtfully maintained, cozy, and tastefully decorated, with plenty of space to relax. Even though it rained for most of our trip, we were more than comfortable indoors and still had a great time exploring the area. The location is perfect—tucked between a peaceful lake and a quiet pond, offering a real sense of escape, yet still just a short drive to beaches, restaurants, shops, and anything else you might need on the Cape. It’s a great spot for both relaxing and adventuring. We’d definitely love to come back and highly recommend it to anyone looking for a special place to stay! Thank you Allison!
Guest favourite
Home in Barnstable
4.92 out of 5 average rating, 38 reviews

Charming Cozy Coastal Retreat|Pet Friendly|EV

AlexandraRating, 5 stars3 weeks ago
My Family and I stayed at Ivy’s cozy Cape Cod home for 2 months. Ivy’s house is very comfortable and clean, the neighborhood is quiet and safe, and Ivy is an excellent host! We would love to come back and stay again during the summer! Thanks Ivy!
Top guest favourite
Home in Hyannis Port
5 out of 5 average rating, 12 reviews

Beach Cottage

JamesRating, 5 stars9 months ago
I grew up going to Cape Cod my whole childhood. Absolutely loved staying at this cottage and in this area of West Hyannis. Would recommend to anyone looking to go to the Cape.
Top guest favourite
Home in Harwich
4.93 out of 5 average rating, 46 reviews

Waterfront★ Pvt Beach ★ On Bike Path ★Bikes★Kayaks

DesireeRating, 5 stars3 days ago
Aruna's cottage was even more beautiful, both inside and out, than the photos. The interior was gorgeous, light filled and many decorative touches that made it feel like a 5-star hotel. The furniture was comfortable and there were many lamps which made reading in the evenings very easy. The art TV picture was very nice when the TV wasn't on rather than looking at a big, black screen. We used the dining table with statement chandelier for all our meals. There were all the kitchen pots, pans and utensils we needed. The refrigerator ice maker and water features were appreciated. Both showers were outstanding in function and beauty. Everything was spotless. The patio was so comfortable with a huge umbrella to shade us while we enjoyed the lake view which was ever changing. A highlight was when a huge turtle came out of the lake and walked across the yard. The Cape Cod Rail Trail is just off the property and is screened by a beautiful, tall white fence and evergreens.
Guest favourite
Home in Barnstable
4.93 out of 5 average rating, 45 reviews

Walk2Lake | Fence | Cragiville | 3Livings | Pet AC

VictoriaRating, 5 stars1 month ago
The house is nice, large, we had a rest with the whole family, 9 people, plenty of space, there is everything you need in the kitchen. Good quiet location!!!
Guest favourite
Home in South Yarmouth
5 out of 5 average rating, 15 reviews

Gorgeous Renovation - Boat Dock, Hot Tub, 5 Beds!

NoahRating, 5 stars1 month ago
This property is on another level. It’s the four seasons of Airbnb. It’s such an immaculate place to stay and we loved every part of it. The cleanliness, the high quality of the essentials, the coziness, ambience and so much more was truly worth the stay.
Top guest favourite
Home in Centerville
5 out of 5 average rating, 37 reviews

Lake charm

AmyRating, 5 starstoday
We had a wonderful long weekend! The home was beautiful, clean and peaceful! Excellent communication! We could not have asked for more!!!
Top guest favourite
Home in Barnstable
5 out of 5 average rating, 13 reviews

Wedgewood Cottage (Available Year Round!)

FrankRating, 5 stars4 months ago
I have stayed at Susan's house before and we loved it. we had company this time. we had a wedding for my nephew and I brought my parents and my sister and her family and her two children. they absolutely love the house. it was so accommodating for all of us. we had our own space. love the kitchen! the living room is absolutely amazing with the fireplace and it made our whole weekend such a memorable one. we are so thankful for this house and for Susan. thank you so much!

Quick stats about house rentals in Osterville, Barnstable

  • Total rentals

    120 properties

  • Nightly prices starting at

    $90 SGD before taxes and fees

  • Total number of reviews

    1.9K reviews

  • Family-friendly rentals

    110 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    20 properties have a pool

Destinations to explore