Osterville vacation rentals

We found 313 vacation rentals — enter your dates for availability

Discover a selection of 77 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.
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Osterville offers a relaxed Cape Cod experience

A coastal village on the southern shores of Barnstable, Osterville offers a relaxed setting for any getaway to the Cape Cod region. Although the town is primarily residential, visitors find appeal in its charming main street, exclusive shopping and, of course, the obligatory inlets and harbors, ideal for those hoping to indulge in a spot of fishing or boating. Alongside these highlights, Osterville vacation rentals offer easy access to area attractions such as Centerville's Craigville Beach and the stunning Cape Cod National Seashore, making the village the perfect destination whether staying with family, friends or both.

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 Carousel (5.3 mi / 8.5 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)
  • Cape Cod Lavender Farm (16.4 mi / 26.4 km)

Downtime in Osterville

The village's pretty Main Street is a must-visit during any stay in an Osterville vacation rental, and one where you can spend an idyllic morning stocking up on everything from Cape Cod fashions to kitsch handmade lighthouses for your home. If you've got kids in tow, it's worth checking out the nearby Osterville Village Library, popular thanks to its lively calendar of events for young readers. Otherwise, swing by one of Main Street's cafes for a spot of lunch. The option to enjoy a picnic beside the lily pond at Armstrong-Kelley Park makes getting lunch to go a fine idea indeed.

Blissful summers in Osterville

The population of Osterville swells during the summer months of July and August when vacationers and 2nd-homers alike are drawn to the area by the seemingly endless sunny days. The popularity of the summer months means it's worth booking your preferred Osterville vacation rental well in advance to avoid disappointment. If fewer crowds are more your style, May, June, September and October, the so-called shoulder season months, can be a good bet. Winter getaways see rental rates at their lowest, but the temperature isn't all that great, leaving topping up your tan largely out of the question.

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 (5.2 mi / 8.3 km)
  • Kalmus Beach (5.8 mi / 9.3 km)
  • Sandy Neck Beach (7.7 mi / 12.4 km)
  • Seagull Beach (8.4 mi / 13.5 km)
  • East Sandwich Beach (9.2 mi / 14.9 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?
Among the more popular locations to get a vacation property in Osterville is Wianno. Find your perfect stay with Vrbo and experience this area just like a local.
What is the most popular type of vacation rental accommodation in Osterville?
Cottages are the most popular kind 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 many shapes and sizes. Browse our options to find your perfect match.
How much does it cost to rent a vacation rental in Osterville?
A range of factors influence what you’ll pay for a vacation rental in Osterville, including the length of stay, season and type of property. However, all our vacation homes have one thing in common — excellent value. Just enter your travel dates to find your dream escape.
How much does it cost to rent a beach house in Osterville?
When you travel and the size and style of the property will influence the cost of your beachside vacation rental. Enter your Osterville travel dates to see all your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to choose the amenities and features you want in your beach house.
Are there pet-friendly vacation rentals in Osterville?
Yes. There are. You can choose from 80 vacation rentals that allow pets in Osterville. Several of our pet-friendly vacation rentals even come with a garden for your furry friend to play in, dog beds, complimentary treats and proximity to parks or green space. Apply the “Pets allowed” filter to find a vacation home on Vrbo that’s pawfect.
Can I rent a house with a pool in Osterville?
Mark the “pool” box in our filter tool and you can choose from 22 houses with private pools in Osterville on Vrbo. Lazy soak or races and ball games? Leisure activities are up to you when your vacation home has a swimming pool.
What are popular rental amenities in Osterville?
A water view, a firepit and a nearby river are the most popular rental amenities in Osterville. Whether you’re planning to travel on your own, with your sweetheart or a group of dear friends, Vrbo will help you find a vacation home that suits your tastes with a load of extras you’ll love.
Are there large group vacation rentals in Osterville?
Osterville has 19 vacation properties that can cater to 10 or more guests. These properties come with enough space to share good times with friends and family.
Are there vacation rentals in Osterville that welcome kids?
With 73 family-friendly vacation homes to select from in Osterville, now is a superb time to introduce the kiddos to the excitement of travel. Simply click on our “Properties good for families” filter box to find stays loaded with amenities perfect for traveling families, like extra bedrooms, private pools, entertainment areas and hot tubs.
What are the top attractions for families in Osterville?
If you’re searching for some entertainment for the family close to the center of Osterville, check out Dowses Beach.
Are there one-bedroom vacation rentals in Osterville?
Yes, you can pick from three one-bedroom rentals in Osterville. Whether you’re on the lookout for a cozy cottage or an upmarket condo, Vrbo’s one-bedroom properties are perfect if you don’t need lots of space. One of the major perks of having your own digs? You’ll never need to share your trip with strangers.
Can I find two-bedroom vacation rentals in Osterville?
Osterville has 11 two-bedroom properties for you to pick from. Enjoy a vacation home with all the comfort and space you need at a price you’ll love on Vrbo.
Are there vacation rentals with WiFi in Osterville?
There are 25 vacation rentals with WiFi in Osterville. If you want to disconnect from daily life on your break, but still want to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Osterville?
Osterville has 75 vacation rentals where you’ll be able to kick back in air-conditioned comfort. To find a property on Vrbo that features this perk, enter your desired travel dates and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Osterville?
The minimum required age is generally 16, 18 or 21. It can change across properties on Vrbo, so look at the rules of your chosen Osterville vacation rental before booking your stay.
How long can I rent a vacation rental in Osterville for?
How long you can book a vacation rental in Osterville is up to the property. Just enter your selected travel dates to display a list of options offering extended stays. With plenty of creature comforts like washing machines and kitchens, as well as some offering weekly or monthly discounted prices, you’re sure to get a perfect place to call your home away from home in Osterville.
Does Vrbo offer discounts for vacation homes in Osterville?
On Vrbo, we’ve got plenty of amazing discounts and deals for Osterville. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re off on a mini vacay or a longer stay, Vrbo offers lots of options for every budget and style.

More Vacation Rentals ideas

People also search for