Osterville holiday homes

We found 313 holiday rentals — enter your dates for availability

Discover a selection of 75 homes and other holiday rentals in Osterville that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Osterville getaway

Learn about the unique charm of Osterville with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Osterville

Are you hoping to find things to do in the area? Venture out of your cosy holiday rental and experience everything that Osterville has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Cape Codder Water Park (5 mi / 8.1 km)
  • Cape Cod Inflatable Park (8 mi / 12.9 km)
  • Shining Sea Bikeway (13.1 mi / 21.2 km)
  • Water Wizz (16.6 mi / 26.7 km)
  • Hyannis Youth & Community Center (5.2 mi / 8.4 km)
  • Gold Coast Parasailing & Jet Ski (8.6 mi / 13.8 km)

Exploring the natural landscape of Osterville

Whether you're an adventurous traveller or just want to appreciate the scenery, Osterville is a great spot to appreciate mother nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Craigville Beach (2.5 mi / 4 km)
  • Popponesset Beach (5.4 mi / 8.7 km)
  • Kalmus Beach (5.8 mi / 9.3 km)
  • Sandy Neck Beach (7.6 mi / 12.3 km)
  • Seagull Beach (8.4 mi / 13.5 km)
  • East Sandwich Beach (9.2 mi / 14.9 km)

Transport to and around Osterville

The nearest airport is in Hyannis, MA (HYA-Barnstable Municipal), located 5.8 mi (9.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Vineyard Haven, MA (MVY-Martha's Vineyard), which is 20.2 mi (32.5 km) away.

Frequently asked questions

What is the best area to stay in Osterville when booking a holiday home?
One of the more in-demand neighbourhoods to book a holiday home in Osterville is Wianno. Find your perfect stay on Bookabach and explore this area as a local.
What is the most popular type of holiday home accommodation in Osterville?
Houses are the most popular type of holiday home in Osterville, according to our data. Even if you’ve got a different idea about what you’d like, Bookabach has properties in loads of sizes and shapes. Browse our options to find your perfect match.
How much does it cost to rent a holiday home in Osterville?
Different things can determine what you’ll pay for your holiday home in Osterville, including the season, type of property and length of stay. Still, all Bookabach homes have one thing in common — amazing value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Osterville?
The average price for a holiday home by the beach in Osterville depends on when you’ll be there and the type and size of property you’re searching for. Find prices quickly and easily on Bookabach by entering your preferred travel dates and destination. Then use the filter tool to choose the number of bedrooms and amenities that you need, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday homes in Osterville?
Pack a travel bag for your pooch because Osterville has 75 holiday homes that roll out the welcome mat to pets. Let your furriest friend have fun with the family at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates and destination, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Osterville?
Pack your swimsuit and goggles, because there are 17 houses with a private pool in Osterville. Make a booking at one of these popular holiday homes and let every day be a pool day. Simply enter your travel dates into Bookabach, then check the “pool” filter to find the perfect place for a splashing good time!
What are popular home amenities in Osterville?
The most popular home amenities people are looking for in Osterville are a fireplace, a barbecue grill and a water view. Whether you’re holidaying with family, buddies or even pets, Bookabach holiday properties have the best amenities for making epic memories with the people who matter most.
Are there large group holiday homes in Osterville?
Osterville has 17 holiday properties that can host 10 or more guests. These properties come with the space you need to enjoy good times with your favourite people.
Are there holiday homes in Osterville that welcome kids?
Osterville has 74 family-friendly holiday homes to choose from. And finding a stay that welcomes children is easy with our “Properties good for families” filter. As well as having the entire place to yourselves, you’ll enjoy access to amenities and perks like multiple bedrooms, kitchens and private pools.
What are the top attractions for families in Osterville?
Keep the kids amused at these fantastic family-friendly attractions in Osterville:

  • Cape Codder Water Park
  • Cape Cod Inflatable Park
  • Craigville Beach

Are there one-bedroom holiday homes in Osterville?
Yes, you can pick from three one-bedroom homes in Osterville. Whether you’d like a cosy cottage or a cabin, Bookabach’s one-bedroom properties are perfect if you don’t need loads of space. One of the best parts about having your own pad? You won’t ever have to share your adventure with strangers.
Can I find two-bedroom holiday homes in Osterville?
Osterville has 10 two-bedroom holiday properties to pick from. Discover a holiday home with all the space and comfort you want at a fantastic price on Bookabach.
Are there holiday homes with WiFi in Osterville?
Whether you want to stay in touch with world events, send a few emails or surf your social networks, there are 24 holiday homes with WiFi in Osterville. Check the “WiFi” box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in Osterville?
Pick from 72 holiday homes with air conditioning in Osterville providing that cooling breeze and extra element of comfort. Enter your chosen travel dates and then use our filter tool to locate stays with air conditioning.
How old do you have to be to rent a holiday home in Osterville?
You’ll need to check with the Osterville holiday home you’re looking at on Bookabach as the age limit differs. However, generally it’s 16, 18 or 21.
How long can I rent a holiday home in Osterville for?
The amount of time you can book an Osterville holiday home for depends on the property. Just tap in your preferred travel dates to see options offering extended stays. They come with all you need to make your extended getaway more enjoyable and convenient, like kitchens and backyards. Some Bookabach holiday properties may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

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