Osterville holiday lettings

We found 317 holiday rentals — enter your dates for availability

Discover a selection of 76 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.

Holiday rentals with weekly discounts - Osterville

Showing deals for:10 Oct - 17 Oct

Why visit Osterville

  • Picturesque beaches: Enjoy the serene and beautiful beaches that Osterville has to offer, perfect for relaxation.
  • Cultural insights: Visit the Osterville Historical Society Museum and the Osterville Village Library for a glimpse into local history.
  • Charming village atmosphere: Stroll through Osterville Village, featuring quaint shops and delightful eateries.
  • Scenic coastal walks: Take romantic walks along Cape Cod's stunning coastline, immersing yourself in natural beauty.
  • Diverse accommodation options: Choose from private vacation homes, cosy cottages, and modern condos for a comfortable stay.

Popular types of accommodation in Osterville

Planning a getaway to Osterville? You're in for a treat! This charming coastal town offers a delightful selection of accommodation options, including houses, cosy cottages, and modern condos. Whether you're searching for Osterville hotels or looking to rent a home, our vacation rentals provide the perfect base for your adventures. Explore your choices and find the ideal Osterville rental for a memorable stay!

  • Houses: The top choice for holidaymakers in Osterville, offering spacious and comfortable stays ideal for families or groups.
  • Cottages: A charming option for those seeking a quaint and cosy atmosphere, perfect for a romantic getaway or peaceful retreat.
  • Condos: A modern accommodation type providing convenience and amenities, suitable for travellers who enjoy a bit of luxury.
  • Flats: A practical choice for those looking for self-catering options in bustling areas.
  • Cabins: A rustic escape for nature lovers, ideal for a tranquil holiday experience.**

Top attractions near Osterville

Osterville, Massachusetts, offers a delightful blend of beach, scenic beauty, and outdoor activities, perfect for a relaxing holiday. Visitors can explore local attractions such as the Osterville Historical Society Museum and the Osterville Village Library, which provide cultural insights. The charming harbour and picturesque beaches further enhance the experience, making it an ideal destination for those seeking both leisure and a touch of history.

  • Hyannis Harbor: A picturesque harbour offering stunning views and a vibrant atmosphere. Enjoy leisurely strolls along the waterfront, watch the boats sail by, and soak up the beach vibes while dining at local eateries.
  • Craigville Beach: Renowned for its soft, golden sands, Craigville Beach is perfect for sunbathing, swimming, and beach games. The laid-back vibe makes it an ideal spot for relaxation and enjoying the coastal scenery.
  • John F. Kennedy Hyannis Museum: Delve into the rich history of the Kennedy family through engaging exhibits. The museum captures the cultural essence of the area, highlighting its connections to the late president.

Things to do recommended for couples

Osterville offers delightful couple experiences. Enjoy a concert at the Cape Cod Melody Tent, only 3.1km away, or take a romantic stroll along the Sandwich Boardwalk, 6.8km away. For a bit of fun, try Putter's Paradise Miniature Golf, just 4.3km from Osterville.

Things to do recommended for families

Families visiting Osterville can enjoy a splashing good time at Cape Codder Water Park, unwind at Veterans Memorial Park, and engage in sports activities at the Hyannis Youth & Community Center, all offering delightful experiences just a short drive away.

Things to do recommended for groups

During your group trip to Osterville, explore the vibrant Mashpee Commons for shopping and entertainment, visit the Cotuit Center for the Arts for a cultural experience, and enjoy a round of golf at the scenic Olde Barnstable Fairgrounds Golf Course, all within a short drive from your accommodation.

Booking with Vrbo is simple

Are you hoping to cut costs on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Osterville

Osterville, Massachusetts, offers a delightful blend of beautiful beaches and charming scenery, perfect for a relaxing getaway. Explore Osterville Village for its quaint shops and eateries, or venture to nearby Barnstable for a taste of history and family-friendly excursions. The area is ideal for romantic strolls along Cape Cod's stunning coastline, ensuring a memorable holiday experience steeped in tranquillity and natural beauty.

  • Cape Cod: Located a mere 5.0km from Osterville, Cape Cod is renowned for its stunning outdoor experiences and picturesque scenery. This popular destination boasts beautiful beaches, ideal for sunbathing and family outings. Visitors can indulge in various activities, including thrilling water parks and challenging golf courses. The local landmarks, such as the breathtaking coastline and charming family beaches, are perfect for creating lasting memories. Whether you're looking to relax by the shore or engage in outdoor adventures, Cape Cod offers a delightful escape.
  • Hyannis: Just 3.7km away from Osterville, Hyannis is a vibrant city that embodies the quintessential beach town atmosphere. Known for its family-friendly vibe, this locale is perfect for those seeking outdoor fun and relaxation. The area features an array of attractions, including a lively water park and cultural experiences like theatres and music concerts. With its stunning beaches and inviting family beaches, Hyannis provides an excellent setting for both leisurely days by the sea and exciting entertainment options.
  • East Sandwich: Situated 5.0km from Osterville, East Sandwich is a charming city that captivates visitors with its beautiful scenery and outdoor activities. Known for its pristine beaches, this area is perfect for beach lovers and nature enthusiasts alike. Families can enjoy playgrounds and explore the local golf courses, while water parks provide thrilling fun for all ages. With its delightful beaches and family-friendly atmosphere, East Sandwich is an ideal spot for a relaxing getaway surrounded by nature's beauty.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

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

No matter if you're travelling with a group, as a family, with your pets, or planning for an extended stay, be sure to refine your search according to your key preferences. Here are some helpful booking tips for Vrbo.

  • Traveling to Osterville with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily refine your search to include all of these options, and more, on Vrbo.
  • Traveling to Osterville with young kids: Journeying with young children can present its difficulties. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Osterville: For many, a family holiday isn’t truly fulfilling without their four-legged companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels completely at home.
  • Planning for a long term stay visiting Osterville: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. 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 your search criteria as well.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides an excellent platform for planning your next adventures, allowing you to create new trips, manage your existing arrangements, and review your bookings. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • 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 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)
  • Englewood Beach (7.3 mi / 11.7 km)
  • Sandy Neck Beach (7.6 mi / 12.3 km)
  • Seagull Beach (8.4 mi / 13.5 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 rental?
One of the more in-demand neighbourhoods to book a holiday 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 holiday rental accommodation in Osterville?
Houses are the most popular type of holiday 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 holiday rental in Osterville?
Different things can determine what you'll pay for your holiday 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 holiday 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 holiday rentals in Osterville?
Pack a travel bag for your pooch because Osterville has 75 holiday rentals that roll out the welcome mat to pets. Let your furriest friend have fun with the family at one of our pet-friendly holiday 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 holiday 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 holidaying with family, buddies or even pets, Vrbo holiday properties have the best amenities for making epic memories with the people who matter most.
Are there large group holiday rentals 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 rentals 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 rentals in Osterville?
Yes, you can pick from three one-bedroom rentals in Osterville. Whether you'd like a cosy 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 holiday rentals 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 Vrbo.
Are there holiday 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 holiday homes with WiFi in Osterville. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find holiday rentals 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 rental in Osterville?
You'll need to check with the Osterville holiday 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 holiday rental 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 Vrbo holiday properties may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

More Holiday Rentals ideas

People also search for