Oak Bluffs vacation rentals

We found 1,915 vacation rentals — enter your dates for availability

Discover a selection of 256 homes, 31 apartments, and other vacation rentals in Oak Bluffs that are perfect for your trip. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, such as parking and a hot tub. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Oak Bluffs

Showing deals for:Jan 2 - Jan 9

Image gallery for Stunning compound steps to Katama Bay, heated pool, dock & amenities

Pool
10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Stunning compound steps to Katama Bay, heated pool, dock & amenities

Edgartown, MA

9% off
Price is $2,604
$18,229 for 7 nights
All fees included
Stunning compound steps to Katama Bay, heated pool, dock & amenities

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Find out more about Oak Bluffs

Find out more about Oak Bluffs

Why visit Oak Bluffs

  • Beautiful Beaches: Relax on stunning beaches offering picturesque views and a perfect spot for sunbathing.
  • Historic Lighthouse: Visit the iconic Oak Bluffs Lighthouse, a charming landmark with rich history.
  • Cultural Experiences: Explore local museums and vibrant neighborhoods that showcase the town's unique heritage.
  • Outdoor Activities: Enjoy a variety of recreational activities, from biking to water sports in the scenic surroundings.
  • Charming Accommodations: Stay in cozy cottages, private homes, or modern condos for a delightful vacation experience.

Popular types of accommodation in Oak Bluffs

Discover your ideal getaway with vacation rentals in Oak Bluffs. From charming houses and cozy cottages to modern condos, there's something for everyone. Whether you’re seeking beach rentals or spacious vacation homes, Oak Bluffs offers a variety of options to suit your needs. Explore the beauty of Martha's Vineyard and make lasting memories with the perfect Oak Bluffs vacation rental.

  • Houses: The top choice for travelers to Oak Bluffs, offering spacious and comfortable accommodations perfect for families or groups.
  • Cottages: A charming option, these quaint homes provide a cozy and inviting atmosphere for a delightful getaway.
  • Condos: Ideal for those seeking modern amenities, condos offer a convenient and stylish stay near the beach.
  • Apartments: A practical choice for solo travelers or couples, apartments provide a home-like environment in the heart of Oak Bluffs.
  • Cabins: For nature enthusiasts, cabins deliver a rustic escape while still being close to local attractions.**

Top attractions in and around Oak Bluffs

Oak Bluffs is perfect for a beach and outdoor vacation, offering stunning scenery and a rich history. Visitors can explore popular attractions such as beautiful beaches, the historic lighthouse, and local museums. With a mix of cultural experiences and outdoor activities, Oak Bluffs caters to travelers seeking both relaxation and adventure in this charming coastal town.

  • Inkwell Beach: A beautiful beach located in Oak Bluffs, Inkwell Beach is known for its vibrant atmosphere, perfect for sunbathing, swimming, and enjoying beach activities with family and friends.
  • Martha's Vineyard Museum: Located 2 miles from Oak Bluffs, this museum offers a deep dive into the rich history and culture of Martha's Vineyard, featuring exhibits that celebrate the island's unique heritage.
  • Circuit Avenue: This lively street in Oak Bluffs is filled with shops, restaurants, and entertainment, providing a bustling city vibe that captures the charm of local culture and community.

Things to do recommended for couples

For a romantic getaway in Oak Bluffs, enjoy a fun round at Island Cove Miniature Golf, just 3 miles away. For a touch of luxury, visit the Cape Cod Country Club, 11 miles down the road. Embrace adventure and create lasting memories together.

Things to do recommended for families

Your family will love the Flying Horses Carousel in Oak Bluffs, offering a delightful outdoor experience. For some relaxation, visit the Fulling Mill Brook Preserve and Mashpee River Reservation, both nearby, where you can enjoy the beauty of nature and unwind together.

Things to do recommended for groups

In Oak Bluffs, groups can enjoy a film at the Martha's Vineyard Film Center, play a round at Farm Neck Golf Club, or bike along the scenic Shining Sea Bikeway for a memorable outdoor adventure.

*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 Oak Bluffs

When traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Oak Bluffs with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Oak Bluffs with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, you might want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oak Bluffs: For many families, a vacation wouldn't feel complete without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and cozy beds to ensure that everyone feels at home.
  • Planning for a long term stay visiting Oak Bluffs: 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Oak Bluffs

Oak Bluffs, Massachusetts, is a charming destination perfect for beach lovers and outdoor enthusiasts. Known for its stunning scenery and beautiful homes, this picturesque town offers exceptional views and a relaxing atmosphere. Explore the vibrant neighborhoods and friendly communities nearby, where you can soak in the breathtaking sights of the beautiful peninsula. Whether you're looking to unwind on the beach or enjoy recreational activities, Oak Bluffs promises an unforgettable vacation experience.

  • Martha's Vineyard: Martha's Vineyard is a picturesque island located 7 miles away from Oak Bluffs, known for its stunning outdoor scenery and pristine beaches. This charming destination offers a variety of activities, from music concerts to relaxing at luxurious resorts and playing a round of golf. Visitors can enjoy the beautiful local beaches, including family-friendly options, and explore serene lakes. The laid-back atmosphere combined with its natural beauty makes Martha's Vineyard an ideal spot for those seeking a quintessential New England experience.
  • Falmouth: Falmouth is a vibrant city situated 7 miles from Oak Bluffs, renowned for its outdoor recreational activities and stunning coastal views. This destination features beautiful beaches, including family-friendly areas, and is perfect for beachgoers and nature lovers alike. Falmouth offers a variety of popular activities, including golfing at private country clubs and educational pursuits. With its charming downtown area and easy access to scenic trails and the Cape, Falmouth provides a great blend of relaxation and adventure.
  • Edgartown: Edgartown, located just 5 miles from Oak Bluffs, is a historic city characterized by its beautiful beaches and scenic landscapes. This destination invites travelers to enjoy outdoor activities such as golf at local courses and leisurely strolls along the waterfront. With family-friendly beaches and serene lakes nearby, Edgartown is perfect for a relaxing getaway. The charming streets lined with historic homes and boutiques add to its appeal, making it a must-visit for anyone exploring Martha's Vineyard.

Best time to go to Oak Bluffs

If you're planning a trip to Oak Bluffs, 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
January35.1°F (1.7°C)Light RainMostly SunnyAverageSlightly Low
February35.1°F (1.7°C)Light RainMostly CloudyAverageSlightly Low
March38.8°F (3.8°C)Light RainMostly SunnyAverageSlightly Low
April46.4°F (8.0°C)Light RainMostly SunnyAverageAverage
May54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
June63.0°F (17.2°C)Light RainMostly SunnyHighSlightly High
July71.1°F (21.7°C)Light RainMostly SunnyHighSlightly High
August71.6°F (22.0°C)Light RainMostly SunnyHighSlightly High
September66.6°F (19.2°C)Light RainMostly SunnyAverageAverage
October58.5°F (14.7°C)Light RainMostly SunnyLowAverage
November48.9°F (9.4°C)Light RainMostly SunnyLowAverage
December41.4°F (5.2°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is a breeze

Are you aiming to save on your upcoming trip? Being open to adjusting your travel dates can help, 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

When you reserve a qualifying Vrbo for your group getaway, you’ll earn OneKeyCash on the full booking amount. Being the organizer has its perks. By joining our One Key rewards program, you can enjoy exclusive member discounts and accumulate OneKeyCash on eligible stays. Sign up today and begin reaping the benefits.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient area to plan new trips, manage your existing plans, or review and sort your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out Trip Boards, head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the beachside setting in Oak Bluffs

Enjoy the wineries and other features of Oak Bluffs. This walkable and scenic city is known for its beaches, shopping and local tours. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Oak Bluffs

Are you looking for top things to see and do in the city? Venture out of your cozy vacation rental and experience everything that makes Oak Bluffs a fun place to get away. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Shining Sea Bikeway (9.2 mi / 14.8 km)
  • Cape Cod Country Club (11.5 mi / 18.5 km)
  • Oak Bluffs Fishing Pier (0.4 mi / 0.7 km)
  • Farm Neck Golf Club (1.2 mi / 2 km)
  • Cape Cod Winery (8.6 mi / 13.8 km)
  • Falmouth Country Club (10 mi / 16.1 km)

Exploring the natural landscape of Oak Bluffs

Whether you're looking for fun outdoor activities or just want to take in the scenery, Oak Bluffs is a great place to get outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Ocean Park (0.3 mi / 0.5 km)
  • Oak Bluffs Town Beach (0.4 mi / 0.7 km)
  • Inkwell Beach (0.5 mi / 0.7 km)
  • Edgartown Beach (2.8 mi / 4.5 km)
  • Lighthouse Beach (4.8 mi / 7.7 km)
  • Lambert's Cove Beach (5.6 mi / 9.1 km)

Seasonal weather in Oak Bluffs

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 68°F.

Transportation to and around Oak Bluffs

The nearest airport is in Vineyard Haven, MA (MVY-Martha's Vineyard), located 5.2 mi (8.3 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Hyannis, MA (HYA-Barnstable Municipal), which is 20.5 mi (32.9 km) away.

Frequently asked questions

What is the best area to stay in Oak Bluffs when booking a vacation rental?
When looking for the best area to stay in Oak Bluffs, Massachusetts, you might want to consider the charming neighborhood surrounding the Oak Bluffs Harbor. This picturesque area is great for vacation rentals, offering stunning waterfront views and easy access to various attractions. The harbor is a hub of activity, where you can enjoy scenic strolls along the shore, dine at local seafood restaurants, and catch ferry rides to neighboring islands.

Another delightful neighborhood is the historic Camp Ground area, renowned for its colorful gingerbread cottages and the iconic Tabernacle. This area not only boasts a unique architectural charm but also offers a tranquil atmosphere, making it an ideal spot for a peaceful getaway. The proximity to the beach and parks enhances its appeal, providing plenty of outdoor activities and scenic spots for relaxation.

Both neighborhoods have a good selection of vacation rental properties, suiting a range of preferences and group sizes. Whether you're seeking a cozy cottage or a spacious home, you'll find options that reflect the inviting spirit of Oak Bluffs.
How much does it cost to rent a vacation home in Oak Bluffs?
Prices for vacation rentals in Oak Bluffs 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 Oak Bluffs 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 Oak Bluffs vacation house rentals?
You can find great discounts on house rentals in Oak Bluffs 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 Oak Bluffs?
For renting a beach house in Oak Bluffs, Massachusetts, the area around East Chop offers beautiful views of the ocean and the picturesque Vineyard Sound. This neighborhood is known for its charming Victorian cottages and proximity to sandy beaches, making it a prime location for travelers seeking a coastal getaway. Many properties in East Chop come equipped with amenities such as spacious decks, outdoor grills, and easy beach access, great for enjoying warm summer evenings.

Additionally, the area near Oak Bluffs Town Beach provides a lively atmosphere, with beach houses that often feature family-friendly amenities like game rooms, outdoor showers, and direct access to the beach. This area is ideal for those who want to be close to local shops, restaurants, and the bustling activity of the town, including the famous Flying Horses Carousel.

For those who prefer a quieter setting, the neighborhoods surrounding the Oak Bluffs Harbor offer quaint waterfront properties with stunning sunset views. Many of these rentals include private docks, kayaks, and bicycles for exploring the scenic coastline and nearby nature trails. Find your rental near the beach in Oak Bluffs.
What is the most popular type of vacation rental accomodation in Oak Bluffs?
In Oak Bluffs, vacation houses are the most popular type of accommodation, with around 235 available throughout the area. These vacation houses are typically spacious, featuring multiple bedrooms, fully equipped kitchens, and outdoor decks or patios for enjoying the pleasant seaside atmosphere. Many are located near the charming Oak Bluffs harbor and the stunning beaches, making them ideal for families or groups seeking a relaxing getaway.

Additionally, there are about 42 apartments and 40 condos available, which offer a more compact living space with similar amenities, such as kitchen facilities and access to communal areas. Approximately 29 cozy cottages can also be found, providing a quaint, homey feel, often located among the scenic landscapes of Martha's Vineyard.
Are there any family house rentals in Oak Bluffs?
In Oak Bluffs, Massachusetts, there are numerous family-friendly vacation rentals available, with around 218 options to choose from. This charming town is known for its beautiful beaches and vibrant atmosphere, making it an excellent choice for families. Many properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces that are superb for children to play.

Visitors can find amenities such as air conditioning and Wi-Fi, ensuring a comfortable and connected stay. Oak Bluffs is also home to attractions like the famous Gingerbread Cottages and the scenic Oak Bluffs Harbor, where families can enjoy leisurely strolls. Additionally, nearby beaches provide opportunities for sunbathing and water sports, adding to the appeal for those looking to create lasting memories. See all family-friendly rentals in Oak Bluffs.
Can I rent a vacation home with a pool or hot tub in Oak Bluffs?
In Oak Bluffs, travelers will find a great selection of vacation homes available for rent that feature pools and hot tubs, with around 70 options to choose from. This charming town on Martha's Vineyard is known for its beautiful beaches, vibrant community, and stunning landscapes. Many of the rentals come equipped with private pools and hot tubs, offering a great spot for relaxation after a day of exploring the area.

Travelers can expect amenities such as spacious outdoor decks, fully equipped kitchens, and comfortable living spaces, ideal for families or groups looking to enjoy their vacation together. Find your rental in Oak Bluffs with a pool or a hot tub.
Can I find long-stay vacation rentals in Oak Bluffs?
A long-stay vacation rental in Oak Bluffs 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 Oak Bluffs?
In Oak Bluffs, there are numerous pet-friendly house rentals available, with around 79 options to choose from. This charming town on Martha's Vineyard is known for its picturesque beaches and vibrant downtown area. Many vacation rentals here offer amenities such as spacious yards, outdoor patios, and fully equipped kitchens, providing a comfortable stay for both travelers and their pets.

The rentals often feature cozy living spaces and convenient access to nearby attractions. Oak Bluffs is home to several pet-friendly points of interest, including the scenic Ocean Park and the beautiful beaches along the shoreline, where pets are welcome. Furthermore, the town's relaxed atmosphere and pet-friendly cafes make it an ideal destination for visitors traveling with their furry companions. See all pet-friendly rentals in Oak Bluffs.
Are there any remote work vacation rentals in Oak Bluffs?
In Oak Bluffs, Massachusetts, travelers seeking remote work vacation rentals will find a substantial selection, with around 318 properties available. This charming island town offers a variety of accommodations that cater to remote workers, featuring amenities such as high-speed Wi-Fi, dedicated workspaces, desks, and comfortable chairs. Many properties also include additional conveniences like laptop workstations, monitors, and safes, ensuring a productive environment for those working away from home.

The scenic surroundings of Oak Bluffs, with its picturesque beaches and vibrant downtown area, provide the great backdrop for balancing work and leisure. Visitors can enjoy local attractions, including the famous Gingerbread Cottages and the beautiful Oak Bluffs Harbor, all while having a comfortable and functional space to work remotely. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oak Bluffs vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oak Bluffs 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 Oak Bluffs?
In Oak Bluffs, popular vacation rental amenities include WiFi, kitchens equipped with essential appliances like blenders and coffee/tea makers, and inviting patios for outdoor relaxation. These amenities enhance the experience for travelers, allowing them to prepare meals and enjoy the coastal atmosphere comfortably. Many rentals are situated close to local attractions such as the vibrant Oak Bluffs Harbor and the iconic Gingerbread Cottages, making it easy for guests to explore the area.
When is the best time to visit Oak Bluffs for a vacation rental?
The best time to visit Oak Bluffs for a vacation rental is during the peak summer months of June to August, with July being the most popular month. This vibrant season attracts families and travelers eager to experience the warm coastal weather, beautiful beaches, and the lively atmosphere of this charming town on Martha's Vineyard.

During these months, visitors enjoy average temperatures ranging from the mid-60s to mid-80s Fahrenheit, ideal for outdoor activities such as beach outings, biking, and exploring the picturesque streets lined with colorful gingerbread cottages. The bustling community hosts numerous events, including art shows and local festivals, creating an energetic vibe that enhances the vacation experience.

For those seeking a more budget-friendly option, consider visiting in November. This quieter month allows you to experience Oak Bluffs in a serene light, with stunning fall foliage and coastal views that are simply breathtaking.
How early should I book a Oak Bluffs vacation rental?
Book your Oak Bluffs 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 Oak Bluffs?
In Oak Bluffs, visitors can enjoy a variety of attractions that showcase the charm of this picturesque town on Martha's Vineyard. The famous Flying Horses Carousel, the oldest operating platform carousel in the United States, is a must-see and is located near the harbor. The vibrant Oak Bluffs Campground, with its colorful gingerbread cottages, offers a unique glimpse into the town's history and is a popular spot for strolls.

Nearby, the scenic beaches, such as Inkwell Beach and Oak Bluffs Town Beach, provide opportunities for sunbathing and swimming. The bustling Circuit Avenue is lined with shops, restaurants, and cafes, where travelers can enjoy local cuisine and browse for souvenirs.
Can I change or cancel my Oak Bluffs home rental booking on Vrbo?
To find Oak Bluffs 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Oak Bluffs 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.

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