Osterville vacation rentals

We found 315 vacation rentals — enter your dates for availability

Discover a selection of 62 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.

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Find out more about Osterville

Why visit Osterville

  • Beautiful Beaches: Enjoy pristine sandy shores and calm waters that are perfect for relaxation and water activities.
  • Historic Charm: Discover Osterville Village with its picturesque historic houses and rich local history.
  • Outdoor Activities: Take advantage of various outdoor excursions, from kayaking to biking along scenic trails.
  • Luxury Vacation Rentals: Choose from a range of cozy cottages and spacious homes for a comfortable stay.
  • Welcoming Atmosphere: Experience the warm, friendly vibe of this quaint Cape Cod town, ideal for families and couples.

Popular types of accommodation in Osterville

Welcome to Osterville, where you'll find a variety of vacation rental options to suit your needs. Whether you're looking for a cozy cottage, a spacious private vacation home, or a modern condo, Osterville has you covered. Explore our wide selection of available Osterville vacation rentals, including charming home and house rentals, perfect for your Cape Cod getaway. Enjoy your stay with transparency and savings at the forefront of your experience.

  • Houses: The top choice for travelers in Osterville, these homes offer spacious accommodations perfect for families or groups looking for a homey feel.
  • Cottages: A close second, these charming and quaint retreats provide a cozy atmosphere ideal for a romantic getaway or tranquil escape.
  • Condos: These modern and convenient spaces are popular for those seeking a blend of comfort and amenities.
  • Apartments: A practical option, offering flexibility and easy access to local attractions.
  • Cabins: Perfect for nature enthusiasts, these rustic stays provide a serene environment surrounded by the great outdoors.**

Top attractions near Osterville

Osterville, Massachusetts, is perfect for a beach and outdoor vacation, offering stunning scenery and rich history. Explore local attractions like Osterville Village, which features beautiful beaches and historic houses, or visit nearby museums for a cultural experience. Additionally, consider looking into Osterville vacation rentals for a comfortable stay as you enjoy all the outdoor activities and coastal charm that this quaint area has to offer.

  • Hyannis Harbor: A picturesque harbor located 6 miles from Osterville, Hyannis Harbor is perfect for scenic strolls and enjoying the beach vibes. Take in the beautiful views of boats and the waterfront while exploring charming shops and restaurants nearby.
  • Craigville Beach: Situated just 3 miles away, Craigville Beach offers a classic beach experience with its soft sands and gentle waves. Ideal for sunbathing, swimming, and beach games, it's a perfect spot to relax and soak up the sun.
  • John F. Kennedy Hyannis Museum: Located 6 miles from Osterville, this museum showcases the rich history and cultural significance of the Kennedy family in the area. Explore fascinating exhibits and artifacts that highlight their connection to Hyannis.

Things to do recommended for couples

For a romantic getaway in Osterville, catch a show at the nearby Cape Cod Melody Tent for some live music vibes. Stroll hand-in-hand along the Sandwich Boardwalk, or enjoy a fun round at Wild Animal Lagoon mini-golf, perfect for couples seeking adventure together.

Things to do recommended for families

Families will have a blast at the Cape Codder Water Park, just 5 miles from Osterville, enjoying thrilling water slides and family fun. For relaxation, Veterans Memorial Park offers a peaceful retreat 6 miles away, while the Hyannis Youth & Community Center, also 5 miles away, provides exciting sports activities.

Things to do recommended for groups

Your group can enjoy a day at Mashpee Commons for shopping and entertainment, visit the Cotuit Center for the Arts for a cultural experience, and play a round of golf at the Olde Barnstable Fairgrounds Golf Course, all just a short drive from Osterville.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you’re traveling with a group, enjoying a family getaway, bringing along pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Osterville with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Osterville with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities, like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Osterville: For many, a family vacation wouldn’t be the same without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and comfortable beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Osterville: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Osterville

Osterville, Massachusetts, offers a delightful blend of beachside relaxation and charming scenery, perfect for families and couples alike. Explore the idyllic Cape Cod atmosphere with luxury vacation rentals and exquisite homes. Enjoy outdoor excursions, soak in the rich history, and experience the warm, welcoming vibe of this picturesque town. Nearby attractions promise exciting adventures, making Osterville a prime destination for your unforgettable getaway.

  • Cape Cod: Located 8 miles from Osterville, Cape Cod is a quintessential New England getaway known for its stunning coastal scenery and outdoor activities. Visitors can bask on the sandy beaches, explore picturesque lighthouses, and enjoy various water sports. The area is home to numerous golf courses and family-friendly venues, including exciting water parks. Notable attractions include the scenic Cape Cod National Seashore, where you can take in breathtaking ocean views and enjoy nature trails that meander through charming landscapes.
  • Hyannis: Just 6 miles from Osterville, Hyannis is a vibrant hub of activity perfect for families and beach lovers alike. This lively city boasts beautiful beaches and a rich array of outdoor experiences. Visitors can enjoy entertainment options such as theaters and music concerts while indulging in local cuisine at waterfront restaurants. The family-friendly atmosphere is complemented by attractions like the Hyannis Harbor, where you can catch ferry rides to the nearby islands, making it an ideal spot for a day of adventure.
  • South Yarmouth: Situated 10 miles from Osterville, South Yarmouth is a delightful city renowned for its beautiful beaches and outdoor recreation. Ideal for families, this charming destination offers a range of activities including playgrounds and golf courses, as well as thrilling water parks that promise a fun-filled day. The area features scenic landscapes along its coastline, making it perfect for leisurely walks or beach picnics. With its inviting atmosphere and numerous attractions, South Yarmouth is a wonderful addition to your Cape Cod exploration.

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 upcoming vacation? One effective strategy is to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you’ll gain access to exclusive discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board is designed to help you plan your journeys with ease. You can create new trips, manage your ongoing plans, and keep track of your bookings all in one place. Your saved and booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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, Massachusetts, United States of America when booking a vacation rental?
When considering the best area to stay in Osterville, Massachusetts, you'll find that the neighborhood offers a charming blend of coastal charm and local attractions. One of the standout areas is close to the village center, where you'll have easy access to delightful boutiques and cafes that reflect the local culture. This area typically features a variety of vacation rentals, ranging from cozy cottages to more spacious homes, providing plenty of options for visitors.

A highlight of staying in this area is its proximity to the beautiful beaches, such as Dowses Beach, which is great for sunbathing and swimming. Additionally, the nearby Osterville Historical Museum offers a glimpse into the town's rich history and is a lovely place to explore.
How much does it cost to rent a vacation home in Osterville?
Prices for vacation 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 vacation 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 Dowses Beach is a prime location. This picturesque beach features soft sands and calm waters, making it ideal for families and those looking to relax by the shore. Many vacation rentals here offer amenities such as private beach access, outdoor decks with seating, and fully equipped kitchens, superb for preparing meals after a day of sunbathing or swimming.

Additionally, rentals near the Osterville Village Center provide a charming atmosphere with proximity to local shops and restaurants. Here, you can find quaint cottages and larger homes that often feature spacious living areas, landscaped gardens, and outdoor grills for summer barbecues. The neighborhood also offers easy access to nature trails and scenic bike paths, enhancing the outdoor experience.

For a bit more seclusion, consider properties along the shores of the nearby Centerville River, where you can enjoy serene views and perhaps even private docks for boating. Many of these homes come with amenities such as kayaks or paddleboards, making it easy to explore the calm waters.
What is the most popular type of vacation rental accomodation in Osterville?
In Osterville, vacation houses are the most popular type of rental, with about 59 available throughout the area. These homes are typically spacious and well-equipped, featuring multiple bedrooms, fully stocked kitchens, and comfortable living areas, superb for families or groups looking to enjoy the coastal charm of Cape Cod. Many of these rentals also include outdoor spaces such as decks or gardens, ideal for relaxing after a day at the beach. Additionally, there are several charming cottages that provide a cozier option for travelers wanting a more intimate atmosphere.
Are there any family house rentals in Osterville?
In Osterville, Massachusetts, families can choose from a variety of house rentals, with around 47 options available throughout the area. This charming coastal town offers a mix of spacious homes, many featuring large living areas, full kitchens ideal for family meals, and outdoor spaces great for children to play. Some properties even include amenities like private pools, game rooms, and BBQ grills, enhancing the overall experience for guests.

Located on Cape Cod, Osterville is close to beautiful beaches such as Dowses Beach, where families can enjoy sunbathing, swimming, and beachcombing. Additionally, the nearby village center offers quaint shops, local eateries, and recreational activities, making it a great spot for exploring local culture.
Can I rent a vacation home with a pool or hot tub in Osterville?
In Osterville, there are several vacation homes available for rent that feature pools and hot tubs, with around 14 options to choose from. This charming coastal village on Cape Cod offers a serene environment great for relaxation. Many of the properties come equipped with private pools, inviting hot tubs, and spacious outdoor areas ideal for entertaining or enjoying family gatherings.

Travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and often proximity to beautiful beaches and local attractions.
Can I find long-stay vacation rentals in Osterville?
A long-stay vacation rental in Osterville is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Osterville?
In Osterville, travelers will find a variety of pet-friendly house rentals available, with options that cater to different group sizes and preferences. Many of these rentals come equipped with amenities such as spacious backyards, outdoor patios, and fully stocked kitchens, making them ideal for families and groups looking to enjoy a comfortable stay.

The area is known for its charming neighborhoods, where visitors can enjoy the picturesque seaside atmosphere. Nearby, you'll find beautiful beaches and scenic parks that are superb for walks with pets. Notable spots include Dowses Beach, which offers sandy shores and gentle waters, making it a great place for a day of fun with your furry friends. Additionally, local parks often have walking trails and open spaces suitable for leisure activities.
Are there any remote work vacation rentals in Osterville?
In Osterville, Massachusetts, there are numerous options for remote work vacation rentals, with around 64 available. This charming coastal village offers a serene environment ideal for productivity. Many of these properties come equipped with essential amenities for remote work, including high-speed internet and Wi-Fi, ensuring you can stay connected while enjoying your getaway.

Travelers can expect comfortable accommodations featuring dedicated workspaces, spacious living areas, and fully equipped kitchens, making it easy to balance work and leisure. The picturesque surroundings, including proximity to the beautiful beaches of Cape Cod and the tranquil waters of Osterville Bay, provide a superb backdrop for a refreshing work-from-home experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Osterville vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Osterville with parking available—perfect for families or travelers 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 cater to travelers looking for comfort and convenience. Most vacation rentals feature fully equipped kitchens, allowing guests to prepare their own meals. Many properties also come with decks or patios, providing outdoor space to relax and enjoy the coastal breeze. Onsite parking is commonly available, making it easy for visitors to explore the surrounding area. Additionally, rentals often include coffee and tea makers for those who appreciate a warm beverage to start their day.
When is the best time to visit Osterville for a vacation rental?
The best time to book a vacation rental in Osterville is during the summer months, particularly in July, when the town is bustling with activity. This peak season spans from June to August, attracting families and travelers seeking the quintessential Cape Cod experience. With warm temperatures averaging in the mid-70s to low 80s Fahrenheit, it's an ideal time for outdoor adventures, beach days, and leisurely strolls along the picturesque shoreline.

During July, visitors can partake in a variety of local events and enjoy the vibrant setting of the town. The beaches are great for sunbathing and swimming, while nearby attractions such as the Cape Cod Rail Trail offer opportunities for biking and hiking amidst stunning coastal scenery. The lively ambiance makes it easy to connect with fellow travelers and immerse yourself in the seasonal charm of Osterville.

For those looking for a more budget-friendly option, consider visiting in November. This month provides a quieter experience, allowing you to appreciate the beauty of the area without the crowds. Autumn in Osterville showcases lovely fall colors, making it a wonderful time for scenic walks and enjoying local dining options with fewer tourists.
How early should I book a Osterville vacation rental?
Book your Osterville vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Osterville, Massachusetts, United States of America?
In Osterville, visitors can enjoy a quaint coastal experience with several attractions worth exploring. The village itself is known for its charming shops and eateries along Main Street, where travelers can find local boutiques and delicious seafood restaurants. The nearby Osterville Bay is great for those interested in water activities such as kayaking and paddleboarding, offering beautiful views and a serene atmosphere.

For a taste of local history, the Osterville Historical Museum showcases the area's maritime heritage and features exhibits that reflect the community's past. Additionally, nearby Dowses Beach is a popular spot for sunbathing and swimming, providing a relaxing day by the ocean. The local golf courses, such as the Wianno Club, offer scenic views and an opportunity for outdoor recreation.
Can I change or cancel my Osterville home rental booking on Vrbo?
To find Osterville vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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