Osterville vacation rentals

We found 320 vacation rentals — enter your dates for availability

Discover a selection of 76 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

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Find out more about Osterville

Why visit Osterville

  1. Beautiful Beaches: Osterville boasts stunning beaches perfect for relaxation and sunbathing.
  2. Local History Museums: Explore museums that showcase the rich history and culture of the area.
  3. Scenic Harbor Views: Enjoy picturesque views of the harbor and waterfront houses along Oesting Street.
  4. Outdoor Adventures: Engage in various outdoor activities, from kayaking to hiking in nearby neighborhoods.
  5. Charming Village Atmosphere: Discover Osterville Village's family-friendly environment with quaint shops and eateries.

Popular types of accommodation in Osterville

Planning a getaway to Osterville? You're in for a treat! Discover the most popular vacation rentals in this charming destination, including houses, cozy cottages, and stylish condos. Whether you're searching for the perfect Osterville vacation rental home or a relaxing retreat, we’ve got you covered with a variety of options to suit your needs. Enjoy transparency, savings, and reassurance as you find your ideal vacation rental in Osterville!

  • Houses: The most sought-after option in Osterville, offering spacious and comfortable living for families, couples, or groups.
  • Cottages: These charming and cozy retreats are perfect for a quaint getaway by the sea.
  • Condos: Ideal for travelers seeking modern amenities and proximity to local attractions.
  • Apartments: A convenient choice for those looking for a home-like atmosphere during their stay.
  • Cabins: Rustic and inviting, these rentals provide a unique experience in a natural setting.**

Top attractions near Osterville

Osterville, Massachusetts, is perfect for beach lovers and outdoor enthusiasts. Explore beautiful beaches, visit local history museums, and enjoy the scenic harbor. The area caters to those seeking culture and adventure, with highlights like Osterville Adventure and Osterville Mercantile. Whether you're relaxing on the shore or diving into local history, Osterville promises an unforgettable vacation experience.

  1. Hyannis Harbor: A picturesque harbor approximately 6 miles from Osterville, offering stunning waterfront views and a vibrant atmosphere. Enjoy the beach vibes while watching boats come and go, and take advantage of nearby shops and dining options.
  2. Craigville Beach: Located only 3 miles from Osterville, this beautiful beach is perfect for sunbathing and swimming. With its soft sands and welcoming atmosphere, it's an ideal spot for relaxation and enjoying the sun.
  3. John F. Kennedy Hyannis Museum: Situated 6 miles away, this museum celebrates the life and legacy of President Kennedy. Experience the rich culture and history of the area through exhibits and memorabilia related to his time spent in Hyannis.

Things to do recommended for couples

Osterville offers a charming getaway for couples. Enjoy a concert at the Cape Cod Melody Tent for lively entertainment. Stroll hand-in-hand along the romantic Sandwich Boardwalk, or challenge each other to a fun round at Putter's Paradise Miniature Golf for a lighthearted adventure.

Things to do recommended for families

Your family will love the Cape Codder Water Park for thrilling water adventures, relax at Veterans Memorial Park for some wellness time, and engage in sports activities at the Hyannis Youth & Community Center. Each location offers unique fun, just a short drive from Osterville!

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

When you're planning a trip—whether with a group, family, pets, or for an extended stay—it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Osterville with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Osterville with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Osterville: For many families, a trip wouldn’t feel complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds to ensure that everyone feels comfortable and 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 additional preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Osterville

Osterville, Massachusetts, offers a charming blend of beach relaxation and scenic beauty, making it an ideal vacation spot. Explore Osterville Village for its family-friendly atmosphere and historical charm. Enjoy outdoor excursions and art displays in nearby neighborhoods. Don't miss the stunning views of waterfront houses along Oesting Street, and consider renting a cozy home for your stay. With its tranquil ambiance, Osterville is perfect for a memorable getaway.

  • Hyannis: Located 6 miles from Osterville, Hyannis is a vibrant city known for its beautiful beaches and family-friendly outdoor activities. Visitors flock to Hyannis for its array of attractions, including a popular water park, lively theater performances, and music concerts that showcase local talent. The scenic coastline offers stunning views and opportunities for relaxation, while the family beach provides a safe and enjoyable environment for children. Hyannis is also a gateway to Cape Cod, making it an ideal spot for exploring the region.
  • Wianno: Nestled within the area of Osterville, Wianno is a charming village that captivates tourists with its picturesque scenery and beach access. Travelers are drawn to Wianno for its delightful shopping area and mall center, where you can find unique local boutiques and eateries. The village is perfect for outdoor enthusiasts, offering access to family-friendly beaches and the stunning Cape coastline. Whether you're looking to enjoy a leisurely day at the beach or indulge in some retail therapy, Wianno has plenty to offer.
  • West Yarmouth: Situated 8 miles from Osterville, West Yarmouth is a bustling city ideal for families seeking outdoor fun. Known for its beautiful beaches, West Yarmouth offers a variety of attractions, including a thrilling water park, playgrounds for children, and excellent golf courses for enthusiasts. The area is perfect for a day of sun-soaked activities, and families can take advantage of the family beach that provides a safe environment for kids. With its proximity to the Cape and ample recreational options, West Yarmouth is a must-visit destination.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 a breeze

Are you hoping to cut costs on your upcoming journey? One effective strategy is to remain open to adjusting 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 helpful filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ for your booking. Being the planner has its perks! By enrolling in our travel rewards program, One Key, you'll gain immediate access to member discounts and the ability to earn and redeem OneKeyCash™ on eligible reservations. Sign up today to start enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or manage your travel itinerary effortlessly. You can easily locate the properties you’ve saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/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?
Among the more popular locations to get a vacation property in Osterville is Wianno. Find your perfect stay with Vrbo and experience this area just like a local.
What is the most popular type of vacation rental accommodation in Osterville?
Cottages are the most popular kind of vacation rental in Osterville, according to our data. Even if you've got a different idea about what you'd like, Vrbo has properties in many shapes and sizes. Browse our options to find your perfect match.
How much does it cost to rent a vacation rental in Osterville?
A range of factors influence what you'll pay for a vacation rental in Osterville, including the length of stay, season and type of property. However, all our vacation homes have one thing in common --- excellent value. Just enter your travel dates to find your dream escape.
How much does it cost to rent a beach house in Osterville?
When you travel and the size and style of the property will influence the cost of your beachside vacation rental. Enter your Osterville travel dates to see all your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to choose the amenities and features you want in your beach house.
Are there pet-friendly vacation rentals in Osterville?
Yes. There are. You can choose from 80 vacation rentals that allow pets in Osterville. Several of our pet-friendly vacation rentals even come with a garden for your furry friend to play in, dog beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find a vacation home on Vrbo that's pawfect.
Can I rent a house with a pool in Osterville?
Mark the "pool" box in our filter tool and you can choose from 22 houses with private pools in Osterville on Vrbo. Lazy soak or races and ball games? Leisure activities are up to you when your vacation home has a swimming pool.
What are popular rental amenities in Osterville?
A water view, a firepit and a nearby river are the most popular rental amenities in Osterville. Whether you're planning to travel on your own, with your sweetheart or a group of dear friends, Vrbo will help you find a vacation home that suits your tastes with a load of extras you'll love.
Are there large group vacation rentals in Osterville?
Osterville has 19 vacation properties that can cater to 10 or more guests. These properties come with enough space to share good times with friends and family.
Are there vacation rentals in Osterville that welcome kids?
With 73 family-friendly vacation homes to select from in Osterville, now is a superb time to introduce the kiddos to the excitement of travel. Simply click on our "Properties good for families" filter box to find stays loaded with amenities perfect for traveling families, like extra bedrooms, private pools, entertainment areas and hot tubs.
What are the top attractions for families in Osterville?
If you're searching for some entertainment for the family close to the center of Osterville, check out Dowses Beach.
Are there one-bedroom vacation rentals in Osterville?
Yes, you can pick from three one-bedroom rentals in Osterville. Whether you're on the lookout for a cozy cottage or an upmarket condo, Vrbo's one-bedroom properties are perfect if you don't need lots of space. One of the major perks of having your own digs? You'll never need to share your trip with strangers.
Can I find two-bedroom vacation rentals in Osterville?
Osterville has 11 two-bedroom properties for you to pick from. Enjoy a vacation home with all the comfort and space you need at a price you'll love on Vrbo.
Are there vacation rentals with WiFi in Osterville?
There are 25 vacation rentals with WiFi in Osterville. If you want to disconnect from daily life on your break, but still want to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Osterville?
Osterville has 75 vacation rentals where you'll be able to kick back in air-conditioned comfort. To find a property on Vrbo that features this perk, enter your desired travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Osterville?
The minimum required age is generally 16, 18 or 21. It can change across properties on Vrbo, so look at the rules of your chosen Osterville vacation rental before booking your stay.
How long can I rent a vacation rental in Osterville for?
How long you can book a vacation rental in Osterville is up to the property. Just enter your selected travel dates to display a list of options offering extended stays. With plenty of creature comforts like washing machines and kitchens, as well as some offering weekly or monthly discounted prices, you're sure to get a perfect place to call your home away from home in Osterville.
Does Vrbo offer discounts for vacation homes in Osterville?
On Vrbo, we've got plenty of amazing discounts and deals for Osterville. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're off on a mini vacay or a longer stay, Vrbo offers lots of options for every budget and style.

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