Osterville vacation rentals

We found 308 vacation rentals — enter your dates for availability

Discover a selection of 55 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.

Vacation rentals with weekly discounts - Osterville

Showing deals for:Apr 3 - Apr 10

Image gallery for Paradise home in Centerville

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

Paradise home in Centerville

Barnstable

8% off
Price is $787
$5,509 for 7 nights
All fees included
Paradise home in Centerville

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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 when booking a vacation rental?
When considering a vacation rental in Osterville, Massachusetts, a popular area to stay is the charming village center. This area is known for its quaint atmosphere and access to a variety of shops, restaurants, and local art galleries. Staying here places you within walking distance of top attractions like the Osterville Village Library, which often hosts community events, and the beautiful Dowses Beach, superb for relaxing by the water or enjoying a picnic with family and friends.

Another great option is the neighborhood near the Wianno Club, which is renowned for its stunning views and golf course. This area offers a more private and serene environment while still being close to the vibrant village center. Here, you can explore the nearby scenic walking trails and enjoy the picturesque coastal scenery.

In Osterville, you can find a diverse range of vacation rental properties, with options that cater to families, couples, and groups.
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 offers a picturesque coastal experience, particularly around Dowses Beach and Osterville Village. Dowses Beach provides beautiful sandy shores and is superb for families looking to enjoy swimming and sunbathing. Vacation rentals near this beach often include amenities such as outdoor decks, barbecue grills, and private access to the beach, making them ideal for summer gatherings or relaxing afternoons by the sea.

In Osterville Village, travelers can find charming cottages and upscale homes that are just a short distance from both the beach and the village's quaint shops and restaurants. Many of these properties feature modern kitchens, spacious living areas, and some even have pools or hot tubs, providing a comfortable retreat after a day of beach activities. The area also offers scenic views of Osterville Bay, with some rentals boasting waterfront access, allowing guests to enjoy kayaking or paddleboarding right from their doorstep.

Additionally, the proximity to the Cape Cod Rail Trail presents opportunities for biking and walking, enhancing the outdoor experience for visitors. Find your rental near the beach in Osterville.
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 69 available throughout the charming coastal community. These homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and often include outdoor spaces like decks or patios for enjoying the pleasant Massachusetts weather. Many properties are located near the picturesque beaches and local marinas, making them ideal for families and groups looking to relax or engage in water activities. Additionally, there are several cozy cottages scattered around, which provide a more intimate experience, often equipped with essential amenities for a comfortable stay.
Are there any family house rentals in Osterville?
In Osterville, Massachusetts, there are numerous family-friendly vacation rentals available, with around 54 options to choose from. This charming coastal village is known for its scenic beauty and family-friendly atmosphere. Many of these homes feature spacious living areas, fully equipped kitchens, and outdoor decks or patios, superb for gatherings and enjoying the pleasant Cape Cod weather.

Visitors can easily access nearby attractions such as Dowses Beach, which offers soft sand and calm waters, ideal for children. Moreover, the area is close to local parks and nature trails, providing ample opportunities for outdoor activities like hiking and picnicking.

In this locale, travelers can expect amenities that cater to families, including Wi-Fi, laundry facilities, and sometimes even game rooms or play areas. See all family-friendly rentals in Osterville.
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 17 options to choose from. This charming village on Cape Cod is known for its beautiful beaches and serene atmosphere, making it an ideal location for a relaxing getaway. Many of the rentals come with amenities such as private pools, hot tubs, and spacious outdoor areas, great for enjoying the coastal climate. Inside, travelers can expect fully equipped kitchens, cozy living spaces, and often multiple bedrooms, accommodating families or groups comfortably. Find your rental in Osterville with a pool or a hot tub.
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 around 22 options to choose from. This charming Cape Cod village offers vacation homes that typically feature a mix of amenities such as outdoor decks, spacious backyards, and modern kitchens, making them great for families or groups traveling with pets. Many properties are designed to provide a comfortable and relaxing stay, often including features like air conditioning, laundry facilities, and cozy living spaces.

Osterville is located near beautiful beaches, such as Dowses Beach and Joshua's Pond, where pets are welcome during the off-season, providing great opportunities for walks and playtime by the water. The nearby village center offers pet-friendly cafes and shops, ensuring that both travelers and their furry companions have a delightful experience in this picturesque coastal setting. See all pet-friendly rentals in Osterville.
Are there any remote work vacation rentals in Osterville?
In Osterville, Massachusetts, there are a variety of vacation rentals that cater to remote work needs, with around 67 options available. This picturesque village on Cape Cod is known for its charming coastal atmosphere and offers properties that are equipped with essential amenities for a productive work environment. Many rentals feature dedicated office spaces, desks, and high-speed Wi-Fi, making it easy for travelers to stay connected and focused.

Additionally, some properties come with extra comforts like computer monitors, ergonomic desk chairs, and safes for secure storage. The serene surroundings offer a superb setting for balancing work and relaxation. After a day of work, you can enjoy the local beaches, explore the scenic coastline, or visit nearby points of interest such as the Osterville Village Library or the beautiful Dowses Beach. 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 vacation rental amenities often include WiFi, kitchens, and outdoor spaces like patios or decks, which are superb for enjoying the pleasant Massachusetts weather. Many rentals also feature a blender, suiting those who enjoy making smoothies or preparing meals during their stay.
When is the best time to visit Osterville for a vacation rental?
The best time to visit Osterville for a vacation rental is during the peak summer season, which spans from June to August. This vibrant period attracts travelers eager to enjoy the beautiful beaches, charming shops, and outdoor activities that the Cape Cod area is famous for. July, in particular, is the most popular month, where visitors can bask in warm temperatures averaging in the mid-70s to low 80s Fahrenheit, making it ideal for sunbathing, swimming, and sailing.

During these summer months, Osterville buzzes with activity, offering a number of options for outdoor enthusiasts. From kayaking in the calm waters of the Nantucket Sound to exploring scenic walking trails, there's no shortage of adventure just moments away from your vacation rental. The local farmers' markets and quaint waterfront restaurants also provide an excellent opportunity to savor fresh seafood and local produce.

For those looking to enjoy Osterville while being mindful of their budget, November presents an appealing alternative. While temperatures drop to the low 40s to mid-50s Fahrenheit, the tranquility of the off-season allows for peaceful strolls along the beach and a chance to appreciate the natural beauty without the summer crowds.
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?
In Osterville, visitors can enjoy a charming seaside atmosphere with several attractions. The village is known for its beautiful beaches, such as Dowses Beach and Osterville Bay, where families can relax and enjoy water activities. The nearby Osterville Historical Museum offers insights into the area's rich history and coastal culture. For those interested in shopping and dining, the Main Street area features quaint boutiques and local eateries serving fresh seafood and other regional specialties.
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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