Osterville holiday lettings

We found 311 holiday rentals — enter your dates for availability

Discover a selection of 59 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:17 Apr - 24 Apr

Image gallery for Paradise home in Centerville

Pool
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Paradise home in Centerville

Barnstable

7% off
Price is £4,767
for 7 nights, 1 home
£681 per night
includes taxes & fees
Paradise home in Centerville

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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)
  • Cape Cod Lavender Farm (16.4 mi / 26.4 km)
  • Water Wizz (16.6 mi / 26.7 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)
  • Hyannis Harbor (5.8 mi / 9.4 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?
When looking for the best area to stay in Osterville, Massachusetts, a delightful choice would be the village centre. This charming neighbourhood is characterised by its picturesque streets and proximity to both the beach and local amenities. You'll find a variety of holiday rentals here, ranging from quaint cottages to luxurious homes, making it a popular spot for visitors.

Staying in the village centre allows easy access to the stunning Dowses Beach, where you can bask in the sun or enjoy a leisurely stroll along the shore. Additionally, the Osterville Historical Museum offers fascinating insights into the region's rich heritage, providing a great outing for history enthusiasts.
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 Bay is particularly appealing. This picturesque coastal community offers holiday rentals that provide easy access to beautiful sandy beaches, with many properties situated just a short stroll from the water. Travellers can expect amenities such as private decks, outdoor dining areas, and barbecues, which are great for enjoying warm summer evenings. Some homes may also feature spacious living areas, fully equipped kitchens, and multiple bedrooms, suiting families or groups seeking a relaxing getaway.

In addition, the nearby Dowses Beach area is another fantastic option, where beach houses often come with stunning views of Nantucket Sound. Many rentals here boast amenities like outdoor showers, which are ideal for rinsing off after a day at the beach, as well as access to community facilities, including tennis courts and picnic areas. The local charm is enhanced by proximity to quaint shops and dining options in the Osterville village, allowing visitors to immerse themselves in the local culture.
What is the most popular type of holiday rental accomodation in Osterville?
In Osterville, holiday houses are the most popular type of rental, with about 66 available throughout the charming coastal community. These houses often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a cozy feel. Many properties also include outdoor spaces such as decks or gardens, superb for enjoying the pleasant Massachusetts weather. Additionally, several cottages can be found in the area, providing a quaint and cosy alternative for those seeking a more intimate setting.
Are there any family house rentals in Osterville?
In Osterville, Massachusetts, there are numerous family-friendly house rentals available, with around 52 options to choose from. This charming coastal village offers a delightful mix of beach access and local attractions, making it an ideal spot for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for relaxation or play. Visitors can expect amenities such as Wi-Fi, air conditioning, and often private gardens or patios.
Can I rent a holiday home with a pool or hot tub in Osterville?
In Osterville, there are several holiday homes available for rent that include pools and hot tubs, with around 17 options to choose from. This picturesque village, located on Cape Cod, is renowned for its charming coastal atmosphere and proximity to beautiful beaches. Many of the rentals in this area feature private pools, hot tubs, and ample outdoor spaces, great for relaxation and entertaining.
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, Massachusetts, there are numerous pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these properties feature spacious layouts, modern kitchens, and outdoor spaces such as gardens or patios, allowing for relaxation and enjoyment with pets.

The charming village of Osterville is known for its picturesque streets and close proximity to several beaches, where pets are often welcomed during certain seasons. The nearby Dowses Beach offers lovely sandy shores and walking paths, making it a great spot for leisurely strolls with your dog. Additionally, the area boasts local parks and nature trails that are superb for exploring with pets.
Are there any remote work holiday rentals in Osterville?
In Osterville, Massachusetts, there are plenty of remote work-friendly holiday rentals available, with around 68 options to choose from. This charming seaside village offers a tranquil environment ideal for working remotely. Many properties feature dedicated workspaces, including desks and comfortable chairs, ensuring a productive atmosphere. High-speed Wi-Fi is commonly available, along with additional amenities such as safe storage for valuables and sometimes even computer monitors to enhance your setup. 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, holiday rentals typically feature a range of popular amenities that enhance the comfort of guests. Most properties come equipped with kitchens, allowing travellers to prepare their own meals, along with cookware, dishware, and utensils for convenience. Many rentals also include patios, providing outdoor spaces to relax and enjoy the pleasant Massachusetts weather. Additionally, ovens and stovetops are common, giving guests the flexibility to cook a variety of dishes during their stay.
When is the best time to visit Osterville for a holiday rental?
July is the most popular time to visit Osterville, Massachusetts, when the summer sun casts a warm glow over this charming coastal town. The peak season runs from June to August, attracting families and beach lovers eager to enjoy the picturesque beaches, quaint shops, and delightful seafood restaurants that Osterville has to offer. With temperatures often reaching the high 20s Celsius, it's an ideal time for outdoor activities such as kayaking, paddle boarding, and leisurely strolls along the shore.

During this vibrant summer season, visitors can experience firsthand local events, including art fairs and music festivals, creating a lively atmosphere throughout the town. July, in particular, sees an influx of tourists, so if you're looking for a more relaxed experience, consider planning your visit in late August when the crowds begin to thin yet the weather remains pleasant.

For those seeking a more budget-friendly option, November is a fantastic time to explore Osterville. While the summer buzz has subsided, you can enjoy the serene beauty of the area, with autumn leaves creating a stunning backdrop. This quieter month allows for peaceful walks along the beach and opportunities to enjoy local dining without the hustle and bustle of peak season.
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.
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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