Oak Bluffs vacation rentals

We found 1,879 vacation rentals — enter your dates for availability

Discover a selection of 261 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:Feb 13 - Feb 20

Image gallery for OB Cozy-Cottage-Glam off Circuit with Great Outdoor living

Front yard and entrance to side yard
9.6 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

OB Cozy-Cottage-Glam off Circuit with Great Outdoor living

Oak Bluffs, MA

5% off
Price is CA $1,231
CA $10,934 total
includes taxes & fees
OB Cozy-Cottage-Glam off Circuit with Great Outdoor living

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Find out more about Oak Bluffs

Why visit Oak Bluffs

  • Stunning Beaches: Oak Bluffs boasts beautiful beaches perfect for relaxing and soaking up the sun.
  • Historic Charm: Explore the iconic vacation homes and the historic lighthouse that add character to the town.
  • Outdoor Activities: Enjoy various outdoor recreation opportunities, including scenic parks and waterfront activities.
  • Cultural Heritage: Visit local history museums to delve into the rich history of Oak Bluffs.
  • Welcoming Atmosphere: Experience the friendly vibe that encourages exploration and relaxation throughout the area.

Popular types of accommodation in Oak Bluffs

Planning a getaway to Oak Bluffs? You're in for a treat. Discover a variety of accommodations, from charming cottages and houses to stylish condos. Whether you're searching for a beautiful home in Oak Bluffs or a cozy cottage rental, our selection of vacation rentals ensures you’ll find the perfect spot to relax and unwind. Start your adventure today and experience the best Oak Bluffs has to offer.

  • Houses: The top choice for visitors to Oak Bluffs, offering spacious and fully-equipped accommodations perfect for families or groups.
  • Cottages: A delightful second option, these quaint and charming spaces provide a cozy atmosphere for a relaxing getaway.
  • Condos: The third most popular choice, these modern units often feature stunning views and convenient amenities.
  • Apartments: A practical fourth option, ideal for those seeking a home-like experience while exploring the area.
  • Cabins: A rustic fifth choice, perfect for nature enthusiasts looking for a serene escape.**

Top attractions in and around Oak Bluffs

Oak Bluffs offers a delightful vacation experience with its stunning beaches, scenic outdoor spaces, and rich history. Visitors can explore the charming Oak Bluffs Harbour, the historic lighthouse, and local history museums, making it perfect for those seeking culture and adventure. Whether you're lounging by the beach or delving into the area's heritage, Oak Bluffs promises a memorable getaway.

  • Inkwell Beach: Enjoy the sun and sand at Inkwell Beach, a popular spot in Oak Bluffs known for its vibrant beach vibes. It's perfect for swimming and relaxing by the water.
  • Martha's Vineyard Museum: Located 3.2km from Oak Bluffs, this museum offers a glimpse into the rich culture and history of Martha's Vineyard, showcasing fascinating exhibits and artifacts.
  • Circuit Avenue: Experience the lively atmosphere of Circuit Avenue, a bustling street in Oak Bluffs filled with shops, restaurants, and entertainment, embodying the city's vibrant spirit.

Things to do recommended for couples

For a romantic getaway in Oak Bluffs, enjoy a fun round at Island Cove Adventures Mini Golf, only 4.8km away. Then, indulge in some wine tasting at Cape Cod Winery, 14.5km away, where you can savour the romantic atmosphere and entertainment together.

Things to do recommended for families

During your family vacation in Oak Bluffs, enjoy the enchanting Flying Horses Carousel for some outdoor fun. For relaxation, visit Fulling Mill Brook Preserve and Mashpee River Reservation, both offering serene environments just a short drive away.

Things to do recommended for groups

Enjoy a round of golf at Farm Neck Golf Club, soak in the outdoors on the Shining Sea Bikeway, or explore the shops and entertainment at Mashpee Commons, all while experiencing the vibrant local culture of Oak Bluffs with your group.

*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

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Oak Bluffs with a group: Think about how many bedrooms you require, as well as features like a complete kitchen or outdoor areas for group get-togethers. Luckily, you can easily refine your search for these options and more on Vrbo.
  • Traveling to Oak Bluffs with young kids: Traveling with little ones can be quite the adventure. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oak Bluffs: For many families, a trip isn't truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure that every member of the family feels comfortable and 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Oak Bluffs

Oak Bluffs, Massachusetts, is a charming destination perfect for a relaxing beach vacation. Visitors can enjoy beautiful beaches and stunning scenery, along with a friendly atmosphere that invites exploration. Don't miss the iconic vacation homes that line the streets, adding to the town's unique character. Nearby attractions offer plenty of outdoor recreation opportunities, making Oak Bluffs an ideal spot for those looking to unwind and soak in the picturesque surroundings.

  • Martha's Vineyard: Martha's Vineyard is a stunning island destination located 11.3km from Oak Bluffs, renowned for its picturesque scenery and outdoor adventures. Visitors flock to this enchanting locale to enjoy its pristine beaches, charming towns, and lush landscapes. The island boasts a variety of attractions, including music concerts and upscale resorts that cater to all types of vacationers. Explore local landmarks such as family-friendly beaches and serene lakes, perfect for sunbathing or a leisurely stroll. With a rich cultural scene and abundant recreational activities, Martha's Vineyard promises an unforgettable experience for nature lovers and beachgoers alike.
  • Falmouth: Situated 11.3km from Oak Bluffs, Falmouth is a vibrant city that showcases the best of Cape Cod's outdoor charm. The city is known for its stunning beaches and scenic views, making it a popular spot for those seeking relaxation and adventure. Falmouth offers numerous activities, including golfing at private clubs and educational opportunities. Visitors can explore local landmarks like family beaches and the captivating Cape, ideal for a day of exploration. With a welcoming community and diverse attractions, Falmouth is a perfect destination for travelers looking to immerse themselves in coastal beauty.
  • Edgartown: Located just 8.0km from Oak Bluffs, Edgartown is a quintessential New England town that enchants visitors with its historic architecture and waterfront charm. Known for its outdoor and beach experiences, Edgartown features beautiful beaches and serene lakes, perfect for swimming and picnicking. Golf enthusiasts can enjoy premier golf courses and country clubs in the area. With its picturesque streets and rich maritime history, Edgartown offers a delightful blend of relaxation and recreation, making it an ideal spot for a memorable vacation.

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 simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly area where you can easily plan new trips, resume previous ones, or manage your travel arrangements. You’ll see your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/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)
  • Mashpee River Reservation (13.2 mi / 21.2 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)
  • Lambert's Cove Beach (5.6 mi / 9.1 km)
  • Menauhant Beach (6.4 mi / 10.3 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 considering a vacation rental in Oak Bluffs, a popular area to stay is the charming Oak Bluffs Village. This vibrant neighbourhood is renowned for its picturesque streets, colourful gingerbread cottages, and an inviting space. The close proximity to local attractions such as the famous Flying Horses Carousel, which is the oldest operating carousel in the United States, makes it an ideal spot for families and those looking to soak up the local culture.

Another delightful option is the East Chop area, known for its stunning views of the ocean and the classic New England architecture. This neighbourhood offers a more serene environment while still being just a short walk from the bustling village centre. Guests here can easily access the East Chop Lighthouse and enjoy leisurely strolls along the scenic shoreline.
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 travelling 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.
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 is particularly desirable, offering stunning waterfront views and easy access to the beach. Here, you'll find charming cottages and modern homes that often come equipped with outdoor decks, spacious living areas, and fully stocked kitchens, ideal for families and groups seeking a relaxing vacation by the sea. Many properties also feature amenities like private gardens and outdoor grills, superb for enjoying summer barbecues.

Additionally, the proximity to Oak Bluffs' vibrant town centre is a significant draw, with its colourful gingerbread cottages, shops, and restaurants just a short walk away. The nearby Inkwell Beach is another highlight, known for its sandy shores and family-friendly atmosphere, where rental homes may include beach gear and easy access to water sports. 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 rental option, with around 236 available throughout this charming coastal town. These houses often come with spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor patios, making them ideal for families or groups looking to enjoy the area's beautiful beaches and vibrant local culture. Additionally, visitors can find approximately 43 apartments and 41 condos, which provide a more compact and convenient stay, often featuring modern furnishings and easy access to local attractions. Cottages, though less common with about 28 options, offer a quaint and cosy atmosphere for those seeking a great experience.
Are there any family house rentals in Oak Bluffs?
In Oak Bluffs, Massachusetts, there is a substantial selection of family-friendly house rentals, with around 226 properties available. This charming area on Martha's Vineyard is great for families seeking a memorable getaway. Many of these homes provide spacious living areas, full kitchens ideal for preparing family meals, and outdoor spaces for children to enjoy.

Properties often include amenities such as air conditioning, Wi-Fi, and laundry facilities for added convenience. Visitors can explore the picturesque surroundings, including the nearby beaches, vibrant Gingerbread Cottages, and the scenic Oak Bluffs Harbor, all in close proximity to the rental homes.
Can I rent a vacation home with a pool or hot tub in Oak Bluffs?
In Oak Bluffs, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 68 options to choose from. This picturesque town on Martha's Vineyard offers a charming coastal atmosphere, making it a popular destination for travellers seeking relaxation and recreation.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Oak Bluffs?
In Oak Bluffs, there are many pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these properties feature spacious layouts, modern amenities such as fully equipped kitchens, Wi-Fi, and outdoor spaces like patios or gardens where pets can enjoy the fresh air.
Are there any remote work vacation rentals in Oak Bluffs?
In Oak Bluffs, Massachusetts, there is a strong selection of remote work vacation rentals available, with around 337 properties to choose from. This charming town on Martha's Vineyard offers a picturesque backdrop for working remotely, combining beautiful coastal scenery with the conveniences of home. Many of these rentals feature dedicated workspaces, including desks and comfortable office chairs, ensuring a productive environment. Additionally, high-speed Wi-Fi is commonly provided, allowing for seamless connectivity. 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 travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Oak Bluffs?
In Oak Bluffs, popular rental amenities include well-equipped kitchens, which are essential for preparing meals during your stay. Most vacation rentals feature microwaves and refrigerators, making it convenient for guests to store and reheat food. Additionally, cookware, dishware, and utensils are typically provided, ensuring that travellers have everything they need for a comfortable self-catering experience.
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 season from June to August, with July being particularly popular. This vibrant period attracts families and leisure travellers looking to enjoy the picturesque beaches, charming Victorian architecture, and lively atmosphere of Martha's Vineyard. With temperatures averaging around 25 to 30 degrees Celsius, it's the great weather for sunbathing, swimming, and exploring the local shops and eateries.

The summer months are bustling with activity, making it an ideal time for those who thrive on socializings and community events. You can partake in various outdoor activities such as cycling, kayaking, and enjoying the many festivals that take place in the area. The beautiful waterfront views enhance the experience, ensuring that every moment spent outdoors is enjoyable and memorable.

If you're seeking a more tranquil experience, consider visiting in November. This month offers a quieter alternative, great for those who appreciate the off-season charm of Oak Bluffs. You can enjoy leisurely strolls along the beach and take in the stunning coastal scenery without the summer crowds, making it a wonderful time for reflection and relaxation.
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 highlight the charm of this picturesque seaside town. The vibrant Oak Bluffs Harbour is a focal point, where colourful gingerbread cottages line the streets and the famous Flying Horses Carousel, the oldest operating carousel in the United States, offers a nostalgic experience for families.

The nearby Martha's Vineyard Camp Meeting Association grounds are a must-see, with their unique Victorian architecture and beautiful gardens. For those looking to relax, the beaches such as Inkwell Beach provide stunning views and a great spot for sunbathing or swimming.
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 makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy 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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