Discover a selection of 184 vacation rentals in Osterville that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $95 per night, and houses and cottages are popular options for a stay in Osterville. Either way, you'll find a rental for everyone's needs.
Destination guide

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.

Things to do

Cultural attractions near Osterville

If a culture fix is on the agenda, nearby Hyannis serves up the chance to visit the John F. Kennedy Hyannis Museum and the Kennedy Compound, a 6-acre waterfront site that served as a summer residence for one of the country's most beloved presidents. While it's not possible to look inside the site's 3 homes, you can get a good look at the compound from the beach. For those more interested in art, the Cape Cod Museum of Art in Dennis features a varied exhibition schedule. Time your visit to coincide with ARTfull Thursdays, a weekly event offering gallery talks and free admission.


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.

Natural features

Day trips from Osterville

There are few places in the world more scenic than the Cape Cod region, especially over the summer when pristine beaches and clear blue skies are typically the order of the day. See the region at its best by taking a road trip to the Cape Cod National Seashore, a 40-mile stretch of broad sandy beaches and wild cranberry bogs. If you have time to spare, Hyannis Harbor offers ferry rides to both Nantucket and Martha's Vineyard, the latter the larger of the 2 islands and a great place to cycle through quintessential harbor towns and lush farmland.

How to get there

Traveling to and around Osterville

The nearest airport is in Hyannis, MA (HYA-Barnstable Municipal), located 5.9 mi (9.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Vineyard Haven, MA (MVY-Martha's Vineyard), which is 20.1 mi (32.4 km) away.

How many vacation rentals are available around Osterville?

Our 2020 property listings offer a large selection of 184 vacation rentals around Osterville. From 154 house rentals to 22 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Osterville?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Osterville:

  • Hyannis: 834 vacation rentals
  • Katama: 253 vacation rentals
  • Dennis Port: 827 vacation rentals
  • South Yarmouth: 244 vacation rentals
  • Harwich Port: 872 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Osterville?

Vrbo offers a large selection of vacation rentals near lovely places in Osterville. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Stand Up & Paddle Cape Cod: 3,482 vacation rentals
  • Craigville Beach: 3,608 vacation rentals
  • Hyannis Harbor: 3,553 vacation rentals
  • Cape Cod Museum of Art: 3,830 vacation rentals
  • Corporation Beach: 3,776 vacation rentals

But there are many other points of interest around Osterville listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Osterville?

Yes, of course. Vrbo has 154 Houses in Osterville. Our other popular types of vacation rentals in Osterville include:

  • Cottages: 22 rentals available
  • Bungalows: 22 rentals available
  • Cabins: 22 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Osterville?

Yes, you can select your preferred vacation rental with pool among our 24 vacation rentals with pool available in Osterville. Please use our search bar to access the selection of vacation rentals available.

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