Osterville vacation rentals

We found 319 vacation rentals — enter your dates for availability

Discover a selection of 75 homes and other vacation rentals in Osterville that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a hot tub. You'll be sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Osterville

Showing deals for:Nov 14 - Nov 21
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Find out more about Osterville

Find out more about Osterville

Why visit Osterville

  1. Beautiful Beaches: Enjoy stunning sandy shores perfect for sunbathing, swimming, and beachcombing.
  2. Charming Village Centre: Stroll through quaint shops and art galleries that showcase local craftsmanship.
  3. Scenic Harbour: Experience picturesque views and recreational activities along the tranquil waterfront.
  4. Outdoor Adventures: Engage in family-friendly excursions and explore nearby islands offering breathtaking coastal scenery.
  5. Diverse Accommodation: Choose from cozy vacation rentals, cottages, and condos with fantastic amenities for a comfortable stay.

Popular types of accommodation in Osterville

Discover the charm of Osterville with our diverse selection of vacation rentals. Whether you're seeking a cozy private vacation home, a quaint cottage, or a modern condo, we have options to suit every traveller. Many of our Barnstable vacation rentals include fantastic amenities, such as pools, ensuring your stay is both relaxing and enjoyable. Let us help you find the perfect holiday cottage for your next getaway!

  • Houses: The top choice for visitors in Osterville, these homes offer spacious and comfortable stays, ideal for families or groups.
  • Cottages: A charming option, cottages provide a cozy atmosphere and are perfect for those seeking a quaint getaway.
  • Condos: These modern accommodations are great for those who appreciate convenience and amenities close to the beach.
  • Apartments: Ideal for shorter stays, apartments offer a home-like feel with essential facilities.
  • Cabins: Perfect for nature lovers, cabins provide a rustic retreat amidst the beautiful surroundings.**

Top attractions in Osterville

Osterville, Massachusetts, is an ideal destination for beach lovers and outdoor enthusiasts alike. Visitors can explore beautiful beaches, delve into local history at nearby museums, and enjoy the scenic harbour. This charming locale offers a perfect blend of culture and nature, making it a delightful getaway for those seeking both relaxation and adventure.

  1. Hyannis Harbor: Located 9.7km from Osterville, this picturesque harbor offers stunning scenery and a vibrant beach atmosphere, perfect for leisurely strolls and enjoying fresh seafood.
  2. Craigville Beach: Just 4.8km away, Craigville Beach boasts soft sands and gentle waves, making it an ideal spot for sunbathing, swimming, and beach activities.
  3. John F. Kennedy Hyannis Museum: Located 9.7km from Osterville, this museum immerses visitors in the rich culture and history of the Kennedy family, showcasing their connection to Cape Cod.

Things to do recommended for couples

For a romantic getaway in Osterville, catch a show at the lively Cape Cod Melody Tent, just 8.0km away. Stroll hand in hand along the charming Sandwich Boardwalk, 17.7km away, or enjoy some fun at Putter's Paradise Miniature Golf, located 11.3km from your base.

Things to do recommended for families

In Osterville, families can splash around at the Cape Codder Water Park, relax at Veterans Memorial Park, or enjoy sports activities at the Hyannis Youth & Community Center, all within a short drive for a fun-filled vacation experience.

Things to do recommended for groups

Explore Mashpee Commons for shopping and dining, just 8.0km from Osterville. Enjoy a cultural evening at the Cotuit Center for the Arts, located 4.8km away. For outdoor fun, visit the Olde Barnstable Fairgrounds Golf Course, a mere 6.4km from your base.

What do I need to keep in mind when booking a vacation in Osterville

If you're planning a trip with friends, family, pets, or seeking extended stays, it's important to prioritise your preferences when searching. Here are some helpful booking tips for using Vrbo.

  • Traveling to Osterville with a group: Take into account how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Osterville with young kids: Travelling with young children can present its challenges. It’s important to prioritize their comfort and safety, along with having access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Osterville: For many families, a trip isn’t truly complete without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Osterville: If you’re in search of vacation rentals with great rates for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay in Osterville

Osterville, Massachusetts, is a charming destination perfect for a relaxed beach vacation. Explore the picturesque village centre with its quaint shops and galleries, or take a short trip to nearby islands for stunning coastal views. Enjoy family-friendly excursions and soak in the area's rich history while wandering through scenic harbours. With its inviting atmosphere and outdoor activities, Osterville and its surrounding regions offer a delightful getaway for every traveller.

  • Hyannis: Located 9.7km away from Osterville, Hyannis is a bustling city known for its beautiful beaches and family-friendly atmosphere. Visitors flock to this vibrant hub for an array of outdoor experiences, including sunbathing at local beaches and enjoying water activities. Attractions such as water parks, theatres, and music concerts provide entertainment for all ages. The iconic Cape Cod scenery, along with well-maintained parks, makes Hyannis a prime spot for relaxation and adventure alike.
  • East Sandwich: Situated 12.9km from Osterville, East Sandwich is a picturesque city that offers stunning coastal scenery and a serene atmosphere. It’s ideal for those seeking a peaceful beach getaway, complete with scenic walking trails and family-friendly activities. Popular attractions include playgrounds and golf courses, perfect for a day of fun in the sun. The charming beach areas and proximity to the Cape enhance the allure of East Sandwich, making it a delightful stop for any traveller.
  • Wianno: Nestled within Osterville, Wianno is a quaint village that embodies the charm of Cape Cod living. This village is perfect for those who appreciate beautiful beaches and stunning landscapes. Visitors can enjoy a variety of local attractions, including shopping areas and amusement rides. Wianno’s close-knit community and educational opportunities make it a unique spot to explore. Its inviting beaches and family-friendly vibe provide an idyllic setting for relaxation and fun.

Best time to go to Osterville

If you're planning a trip to Osterville, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January34.9°F (1.6°C)Light RainMostly SunnyAverageSlightly Low
February34.9°F (1.6°C)Light RainMostly CloudyAverageSlightly Low
March38.5°F (3.6°C)Light RainMostly SunnyAverageSlightly Low
April45.9°F (7.7°C)Light RainMostly SunnyAverageAverage
May54.1°F (12.3°C)Light RainMostly SunnyAverageAverage
June62.6°F (17.0°C)Light RainMostly SunnyModerately HighSlightly High
July70.5°F (21.4°C)Light RainMostly SunnyModerately HighSlightly High
August70.9°F (21.6°C)Light RainMostly SunnyModerately HighSlightly High
September65.8°F (18.8°C)Light RainMostly SunnyAverageAverage
October57.9°F (14.4°C)Light RainMostly SunnyModerately LowAverage
November48.4°F (9.1°C)Light RainMostly SunnyModerately LowAverage
December41.0°F (5.0°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, feel free to use our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, refine your itineraries, or review and manage your bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Osterville getaway

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

Activities and attractions in Osterville

Are you hoping to find attractions to see while you're in town? Venture out of your vacation home and experience everything that makes Osterville a fun spot to vacation. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Cape Codder Water Park (5 mi / 8.1 km)
  • Cape Cod Inflatable Park (8 mi / 12.9 km)
  • Cape Cod Country Club (9 mi / 14.5 km)
  • Shining Sea Bikeway (13.1 mi / 21.2 km)
  • Water Wizz (16.6 mi / 26.7 km)
  • Olde Barnstable Fairgrounds Golf Course (4 mi / 6.5 km)

Exploring the natural landscape of Osterville

Whether you're looking for adventure or just want to take in the scenery, Osterville is a great place to get outside. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Heritage Museums and Gardens (10.2 mi / 16.4 km)

Transportation to and around Osterville

The nearest airport is in Hyannis, MA (HYA-Barnstable Municipal), located 5.8 mi (9.4 km) from the city center. If you can't find a flight that works for your travel itinerary, 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 vacation rental?
One of the more in-demand neighborhoods to book a vacation home in Osterville is Wianno. Find your perfect stay on Vrbo and explore this area as a local.
What is the most popular type of vacation rental accommodation in Osterville?
Houses are the most popular type of vacation rental in Osterville, according to our data. Even if you've got a different idea about what you'd like, Vrbo has properties in loads of sizes and shapes. Browse our options to find your perfect match.
How much does it cost to rent a vacation rental in Osterville?
Different things can determine what you'll pay for your vacation rental in Osterville, including the season, type of property and length of stay. Still, all Vrbo 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 vacation rental 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 Vrbo 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 vacation rentals in Osterville?
Pack a travel bag for your pooch because Osterville has 75 vacation rentals that roll out the welcome mat to pets. Let your furriest friend have fun with the family at one of our pet-friendly vacation rentals on Vrbo. 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 vacation homes and let every day be a pool day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Osterville?
The most popular rental amenities people are looking for in Osterville are a fireplace, a barbecue grill and a water view. Whether you're vacationing with family, buddies or even pets, Vrbo vacation properties have the best amenities for making epic memories with the people who matter most.
Are there large group vacation rentals in Osterville?
Osterville has 17 vacation properties that can host 10 or more guests. These properties come with the space you need to enjoy good times with your favorite people.
Are there vacation rentals in Osterville that welcome kids?
Osterville has 74 family-friendly vacation 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 vacation rentals in Osterville?
Yes, you can pick from three one-bedroom rentals in Osterville. Whether you'd like a cozy cottage or a cabin, Vrbo'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 vacation rentals in Osterville?
Osterville has 10 two-bedroom vacation properties to pick from. Discover a vacation home with all the space and comfort you want at a fantastic price on Vrbo.
Are there vacation rentals 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 vacation homes with WiFi in Osterville. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Osterville?
Pick from 72 vacation 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 vacation rental in Osterville?
You'll need to check with the Osterville vacation home you're looking at on Vrbo as the age limit differs. However, generally it's 16, 18 or 21.
How long can I rent a vacation rental in Osterville for?
The amount of time you can book an Osterville vacation 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 Vrbo vacation properties may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

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