Oak Bluffs vacation rentals

We found 1,896 vacation rentals — enter your dates for availability

Discover a selection of 260 homes, 33 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.

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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)
  • 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)
  • Stand Up & Paddle Cape Cod (15.1 mi / 24.3 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 the best area to stay in Oak Bluffs, Massachusetts for a vacation rental, the charming neighbourhood of Oak Bluffs itself is a fantastic choice. This area is renowned for its vibrant setting and picturesque setting, making it a favourite among visitors. The neighbourhood boasts a delightful array of colourful Victorian gingerbread cottages, which add a unique charm to the surroundings. One of the top attractions here is the famous Flying Horses Carousel, the oldest operating carousel in the United States, where both children and adults can enjoy a ride on beautifully crafted wooden horses.

Another highlight of Oak Bluffs is the serene Oak Bluffs Town Beach, great for sunbathing, swimming, or simply enjoying the stunning views of the Atlantic Ocean. The area has a variety of vacation rental properties, ranging from quaint cottages to larger family homes, providing options to suit different needs and budgets. Staying in Oak Bluffs not only offers easy access to these attractions but also places you in a lively hub with shops, restaurants, and local art galleries that contribute to the area's vibrant community spirit.
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, the area around the scenic East Chop offers a delightful selection of properties with stunning views of the ocean. Many houses here feature amenities such as spacious decks, private beach access, and well-equipped kitchens, making them ideal for families and groups seeking a relaxing seaside retreat. The proximity to the East Chop Lighthouse adds a charming touch to the neighbourhood, and guests can enjoy leisurely walks along the coastline.

Another great option is the area near Oak Bluffs Town Beach, known for its vibrant setting and easy accessibility. Here, visitors can find beach houses that often come with outdoor showers, BBQ grills, and picnic areas, superb for entertaining and enjoying warm summer evenings. Being close to local shops and restaurants enhances the convenience, allowing for a delightful blend of relaxation and exploration.

Furthermore, the nearby Oak Bluffs Ferry Terminal provides easy access to Martha's Vineyard, making it a great base for day trips. The properties in this vicinity typically offer a mix of modern comforts and traditional charm, with many featuring air conditioning, Wi-Fi, and comfortable living spaces.
What is the most popular type of vacation rental accomodation in Oak Bluffs?
In Oak Bluffs, vacation houses are the predominant type of vacation rental, with approximately 864 available in charming neighbourhoods close to the beach and local attractions. These spacious homes typically feature multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or gardens, great for enjoying the pleasant Massachusetts weather. Cottages are also a popular option, with around 104 available, offering a quaint, cosy atmosphere ideal for couples or small families. Many cottages come with essential amenities, including kitchen facilities and comfortable living areas. Additionally, there are about 100 apartments and 40 condos, which cater to those seeking a more compact living space. These rentals often include modern conveniences like Wi-Fi and laundry facilities, making them suitable for longer stays.
Are there any family house rentals in Oak Bluffs?
In Oak Bluffs, Massachusetts, there are numerous family-friendly house rentals available, with around 209 options to choose from. This charming town on Martha's Vineyard is well-suited for families, offering spacious properties that often feature multiple bedrooms, comfortable living areas, and well-equipped kitchens, making meal preparation a breeze. Many homes also come with outdoor spaces where children can play and families can gather for barbecues.

Visitors can enjoy the beautiful beaches, such as Inkwell Beach and Joseph Sylvia State Beach, both of which are great for a day of sun and sand. The vibrant setting of Oak Bluffs is enhanced by attractions like the Flying Horses Carousel and the picturesque Oak Bluffs Campground, known for its colourful gingerbread cottages.
Can I rent a vacation home with a pool or hot tub in Oak Bluffs?
In Oak Bluffs, there are around 14 vacation homes available for rent that feature pools or hot tubs, making it an excellent choice for travellers seeking relaxation and leisure during their stay. This charming town on Martha's Vineyard is known for its vibrant setting and beautiful coastal scenery.

Visitors can find properties in various neighbourhoods, including the picturesque Oak Bluffs Village, where many rentals offer easy access to the beach and local attractions. The amenities in these homes typically include private pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, ideal for both unwinding and entertaining. Some rentals may also provide additional features like outdoor dining spaces and beautifully landscaped gardens, ensuring a delightful vacation experience.
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 a number of pet-friendly house rentals available, with around 56 options for travellers seeking accommodations that welcome their furry companions. Many of these rentals are situated close to the picturesque beaches and charming town centre, allowing for easy access to local shops and eateries. Expect amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, which cater well to families and groups.

The area is known for its vibrant setting, with attractions like the scenic Oak Bluffs Marina and the famous Gingerbread Cottages, both of which provide delightful settings for leisurely strolls with pets. Additionally, nearby parks and open spaces offer ample opportunities for outdoor activities, ensuring that both guests and their pets can enjoy the beautiful natural surroundings.
Are there any remote work vacation rentals in Oak Bluffs?
In Oak Bluffs, Massachusetts, there are a considerable number of remote work vacation rentals available, with around 1,092 options to choose from. This charming town, located on Martha's Vineyard, offers a picturesque seaside atmosphere, ideal for combining work and leisure. Many properties are equipped with essential amenities such as free Wi-Fi, allowing for seamless connectivity while you work.

Travellers can expect a range of accommodations, from cosy cottages to spacious family homes, often featuring dedicated workspaces, comfortable seating, and well-equipped kitchens for preparing meals. The proximity to local attractions like the famous Gingerbread Cottages and the stunning beaches provides a great backdrop for unwinding after a day of remote work. 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 kitchens, which allow guests to prepare their own meals, and outdoor decks or patios ideal for enjoying the pleasant weather. Many rentals also feature blenders for making smoothies or cocktails, alongside onsite parking for convenience. Additionally, travellers can expect coffee and tea makers to help start their mornings right.
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 season from June to August, with July being the most popular month. This vibrant period attracts families and beachgoers eager to enjoy the sun, sand, and the charming atmosphere of Martha's Vineyard. Visitors can indulge in a range of outdoor activities, from relaxing on the beautiful beaches to exploring the quaint streets filled with delightful shops and restaurants.

During these summer months, temperatures typically hover around 20 to 30 degrees Celsius, providing superb conditions for swimming, cycling, and enjoying local events such as the lively fireworks displays and outdoor concerts. The bustling environment is ideal for those who thrive in a lively option, where meeting fellow travellers and soaking in the energy of the island is part of the experience.

If you're looking for a more budget-friendly option, consider visiting in November, when the crowds have thinned and the island offers a peaceful retreat. The crisp autumn air allows for lovely walks and a chance to appreciate the natural beauty of the area without the hustle and bustle of summer tourists.
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 town. The iconic Gingerbread Cottages, located close to the centre, showcase colourful Victorian architecture and are a must-see for those exploring the area. The nearby Oak Bluffs Marina offers scenic views of the harbour and is great for leisurely strolls or dining at waterfront restaurants.

The Flying Horses Carousel, one of the oldest operating carousels in the United States, provides a delightful experience for families and children. For those interested in nature, the beautiful beaches such as Inkwell Beach and Joseph Sylvia State Beach offer opportunities for sunbathing and swimming, along with lovely walking paths.

The town's vibrant nightlife can be experienced at local bars and live music venues, particularly during the summer months when the atmosphere becomes lively with events and gatherings.
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 cabin or a beach house, 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 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.
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.

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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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