Osterville holiday lettings

We found 314 holiday rentals — enter your dates for availability

Discover a selection of 62 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.

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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.

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.

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

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.

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)
  • Stand Up & Paddle Cape Cod (0.2 mi / 0.3 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)
  • Keyes Beach (4.8 mi / 7.8 km)
  • Popponesset Beach (5.4 mi / 8.7 km)
  • Kalmus Beach (5.8 mi / 9.3 km)
  • Hyannis Harbor (5.8 mi / 9.4 km)
  • Lewis Bay (6.5 mi / 10.5 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?
When considering a holiday rental in Osterville, Massachusetts, a popular area to stay is near the charming village centre. This picturesque neighbourhood boasts a delightful array of boutique shops, cafes, and restaurants, making it an ideal spot for those who enjoy being close to local amenities. The village is also renowned for its beautiful beaches, such as Dowses Beach, where visitors can relax and soak up the sun or engage in water activities.

Another appealing area is near the North Bay, which offers stunning waterfront views and a tranquil atmosphere. This part of Osterville is superb for those looking to enjoy nature, with opportunities for boating and fishing right at your doorstep. The proximity to the Osterville Historical Museum adds a cultural touch, allowing guests to explore the rich history of the area.

Overall, Osterville features a selection of attractive properties ranging from charming cottages to more spacious homes.
How much does it cost to rent a holiday home in Osterville?
Prices for holiday rentals in Osterville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Osterville to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Osterville holiday house rentals?
You can find great discounts on house rentals in Osterville on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Osterville?
For renting a beach house in Osterville, Massachusetts, the area around Osterville Village is particularly appealing. This charming village offers a selection of holiday rentals that are close to the sandy shores of Dowses Beach, where visitors can enjoy swimming, sunbathing, and picturesque sunsets. Many properties in this vicinity come equipped with amenities such as private outdoor spaces, barbecue grills, and fully stocked kitchens, superb for family gatherings or friend getaways.

Additionally, properties along the coastline often feature stunning views of Osterville Bay, with some offering direct access to the beach or nearby nature trails. Rentals may include spacious living areas, air conditioning, and outdoor showers to rinse off after a day at the beach.

For those who enjoy a more tranquil setting, the area around Sampson's Island provides serene waterfront properties where guests can relax and unwind. These rentals typically offer amenities like kayaks or paddleboards, enabling easy exploration of the surrounding waters. The close proximity to local shops and restaurants in Osterville Village adds to the convenience, allowing visitors to enjoy the local cuisine and culture.
What is the most popular type of holiday rental accomodation in Osterville?
In Osterville, holiday houses are the most popular type of holiday rental, with approximately 236 available throughout the charming coastal community. These homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor areas for barbecues or relaxing in the sun. Many are situated near picturesque beaches and local attractions, providing easy access to the waterfront and recreational activities. Additionally, there are around 20 cottages available, which offer a quaint, cosy atmosphere great for couples or small families. These cottages often come equipped with essential amenities and are located in tranquil settings, making them an inviting option for a peaceful getaway.
Are there any family house rentals in Osterville?
In Osterville, there is a wealth of family-friendly house rentals to choose from, with around 47 properties available. This charming village, located on Cape Cod, offers a serene atmosphere superb for family gatherings. Many homes feature spacious living areas, fully equipped kitchens ideal for family meals, and outdoor patios or decks where children can play and families can enjoy al fresco dining.

Visitors can explore nearby attractions such as Dowses Beach, which provides a beautiful spot for swimming and sunbathing, or take a stroll along the scenic waterfront. Additionally, the village is close to the lively town of Barnstable, where local shops and restaurants abound.
Can I rent a holiday home with a pool or hot tub in Osterville?
In Osterville, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs, with around 14 options to choose from. This charming coastal village offers a serene atmosphere, superb for a relaxing getaway. Many of these properties come equipped with private swimming pools, hot tubs, and spacious outdoor patios, allowing guests to enjoy the beautiful surroundings while soaking up the sun.

Travellers can expect amenities such as fully equipped kitchens for preparing family meals, comfortable living spaces, and often, proximity to local beaches and marinas. Some rentals may also include features like fire pits for evening gatherings, outdoor dining areas, and lush gardens, enhancing the overall experience.
Can I find long-stay holiday rentals in Osterville?
A long-stay holiday rental in Osterville is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Osterville?
In Osterville, there are several pet-friendly house rentals available, providing a fantastic opportunity for travellers looking to enjoy a coastal getaway with their furry companions. Many of these holiday homes feature modern amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like patios or gardens, superb for pets to roam.

The area is known for its charming atmosphere and proximity to beautiful beaches, making it an ideal destination for pet owners. Nearby, you can find local parks and nature trails where dogs can enjoy walks and playtime. Additionally, the scenic coastline and the tranquil waters of Nantucket Sound offer plenty of opportunities for outdoor activities, including dog-friendly beach access in designated areas.
Are there any remote work holiday rentals in Osterville?
In Osterville, Massachusetts, there is a substantial selection of remote work holiday rentals available, with around 256 options to choose from. This charming coastal village offers a serene environment conducive to productivity, with many properties equipped with essential amenities for remote workers. Travellers can expect to find high-speed internet, free Wi-Fi in rooms, and dedicated desk spaces, ensuring a comfortable working arrangement.

The area is known for its picturesque beaches and vibrant local culture, with nearby points of interest including the charming shops and restaurants of Osterville Village. Many rentals also offer inviting living spaces, ideal for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Osterville holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Osterville with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Osterville?
In Osterville, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature outdoor spaces such as decks or patios, superb for enjoying the pleasant coastal weather. Onsite parking is commonly available, making it convenient for those travelling with a vehicle. Additionally, holiday rentals often provide coffee and tea makers, suiting guests' needs for a comforting morning beverage.
When is the best time to visit Osterville for a holiday rental?
The most popular time to visit Osterville for a holiday rental is during the summer months, particularly in July. This peak season, which runs from June to August, attracts a vibrant mix of families and beachgoers eager to soak up the sun along Cape Cod's beautiful shores. With warm temperatures averaging around 20 to 30 degrees Celsius, it's an ideal time for outdoor activities such as swimming, sailing, and exploring the picturesque coastline.

While July is bustling with visitors enjoying everything from local seafood festivals to beach picnics, you might also consider November as a wonderful alternative for a more tranquil experience. This off-peak month offers a quieter atmosphere where you can appreciate the serene beauty of Osterville, ideal for leisurely walks by the beach and enjoying the crisp autumn air.

For those who value comfort, the summer months provide not only a lively outdoor scene but also an array of charming holiday rentals equipped with modern amenities. Whether you're planning a family getaway or a romantic retreat, you'll find plenty of options that deliver both quality and convenience.

In summary, if you're after the vibrant summer experience filled with activities and a lively community, July is your month.
How early should I book a Osterville holiday rental?
Book your Osterville holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Osterville?
In Osterville, visitors can enjoy a charming coastal experience with a focus on its lovely beaches and local culture. Dowses Beach, known for its soft sands and calm waters, is a popular spot for families and sunbathers alike. Nearby, the village centre offers quaint shops and eateries where travellers can savour local seafood and enjoy the picturesque surroundings.

For those interested in maritime activities, the Osterville Marina provides opportunities for boating and fishing. Additionally, the nearby Cape Cod Museum of Natural History in Brewster, just a short drive away, offers educational exhibits and beautiful walking trails through the area's natural landscapes.
Can I change or cancel my Osterville home rental booking on Vrbo?
To find Osterville holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Osterville holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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