Oak Bluffs vacation rentals

We found 1,846 vacation rentals — enter your dates for availability

Discover a selection of 251 homes, 29 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:May 15 - May 22

Image gallery for Charming 6 Bedroom Cottage in East Chop with Water Views! Walk to Beach & Town!

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10 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)

Charming 6 Bedroom Cottage in East Chop with Water Views! Walk to Beach & Town!

Oak Bluffs

18% off
Price is $1,864
$13,050 for 7 nights
All fees included
Charming 6 Bedroom Cottage in East Chop with Water Views! Walk to Beach & Town!

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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)
  • 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)
  • Tisbury Town Beach (2 mi / 3.3 km)
  • Edgartown Beach (2.8 mi / 4.5 km)
  • Lighthouse Beach (4.8 mi / 7.7 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, Massachusetts, United States of America when booking a vacation rental?
When considering a vacation rental in Oak Bluffs, Massachusetts, the Oak Bluffs Village area is a fantastic choice. This charming neighborhood is known for its vibrant setting, making it a popular spot for visitors. Here, you will find a variety of vacation rental options, from cozy cottages to larger homes, providing a range of accommodations to suit different group sizes and preferences.

One of the highlights of staying in this area is the proximity to the stunning beaches, where you can soak up the sun or enjoy a leisurely stroll along the shoreline. Additionally, the iconic Flying Horses Carousel, the oldest operating platform carousel in the United States, is a must-visit attraction that adds a touch of nostalgia to your stay. The neighborhood also boasts a lively dining scene and boutique shopping, ensuring you'll have plenty of options to explore during your vacation.
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, the area around East Chop offers stunning views of the water and is known for its charming cottages and proximity to the beach. Many properties here come with amenities like spacious decks for enjoying sunsets, outdoor grills for summer barbecues, and easy access to the nearby sandy shores.

The Oak Bluffs Harbor area is also a popular choice, where travelers can find vacation rentals that are close to local shops, restaurants, and the vibrant nightlife of the town. Many of these rentals feature modern conveniences such as full kitchens, air conditioning, and some even have access to swimming pools or beach gear for a fun day by the water.

Additionally, the area near the popular Inkwell Beach is ideal for families, as it offers a relaxed atmosphere with easy beach access. Rentals in this vicinity often include outdoor showers, picnic areas, and spacious living areas for family gatherings. The lively option of the nearby Ocean Park adds to the appeal, providing a great blend of relaxation and entertainment.
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 216 available throughout the area. These homes are typically found in charming neighborhoods near the beach and the famous Oak Bluffs Campground, providing a great home base for enjoying the local attractions. Most vacation houses come equipped with multiple bedrooms, spacious living areas, fully stocked kitchens, and outdoor spaces such as decks or patios, ideal for relaxing after a day of exploring.

Additionally, there are about 26 cottages and 25 apartments available, offering a more intimate and cozy experience. Cottages often feature quaint designs and may include amenities like gardens or outdoor seating, while apartments can provide convenient access to local shops and restaurants.
Are there any family house rentals in Oak Bluffs?
In Oak Bluffs, Massachusetts, there is a substantial selection of family-friendly rentals—around 209 available throughout the area. This charming town, known for its picturesque beaches and vibrant community, offers various properties that cater to families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor decks or patios great for relaxing after a day at the beach.

Additionally, visitors can enjoy amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable and convenient stay. Families will appreciate the proximity to local attractions, including the famous Flying Horses Carousel and the beautiful Oak Bluffs Marina, where they can embark on boating adventures or simply enjoy the scenic views.
Can I rent a vacation home with a pool or hot tub in Oak Bluffs?
In Oak Bluffs, there are several vacation homes available for rent that feature pools and hot tubs, with around 14 options to choose from. This charming town on Martha's Vineyard is well-known for its beautiful beaches and vibrant community. Travelers can expect a variety of amenities in these rentals, including private pools, hot tubs, spacious outdoor areas for relaxation, and fully equipped kitchens, making them superb for families or groups looking to enjoy a luxurious getaway.
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, travelers will find a variety of pet-friendly house rentals available, with around 56 options to choose from. Many of these homes are located close to the vibrant Oak Bluffs town center, where visitors can enjoy charming shops, restaurants, and the iconic Gingerbread Cottages. These vacation rentals often come equipped with desirable amenities such as spacious living areas, modern kitchens, and outdoor spaces like decks or patios, ideal for enjoying the pleasant coastal weather.

For pet owners, the nearby beaches provide an excellent opportunity for walks and playtime. The East Chop Beach and the public beaches around Oak Bluffs are accessible and welcome dogs, making it easy to enjoy the sun and sand with furry companions. Additionally, the scenic paths along the coastline offer beautiful views and a great setting for leisurely strolls.
Are there any remote work vacation rentals in Oak Bluffs?
In Oak Bluffs, Massachusetts, there are plenty of remote work vacation rentals available, with around 273 options to choose from. This charming town on Martha's Vineyard offers a picturesque setting for those looking to blend work and leisure. Travelers can expect properties equipped with essential amenities such as high-speed internet access, free Wi-Fi, and dedicated workspaces or desks, ensuring a comfortable and productive environment.

Many rentals also feature cozy living areas, fully equipped kitchens for preparing meals, and outdoor spaces for relaxing during breaks. The vibrant neighborhood is close to local attractions like the stunning beaches, the iconic gingerbread cottages, and the bustling Oak Bluffs Harbor, making it an ideal spot for remote workers to unwind after hours. 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 kitchens, allowing travelers to prepare their own meals, and decks or patios where guests can relax and enjoy the fresh air. Many rentals also come equipped with blenders, great for whipping up smoothies or cocktails. Onsite parking is a convenient feature for those traveling by car, while coffee and tea makers are essential for starting the day off 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 summer months of June through August, with July being particularly popular among travelers. This vibrant season attracts travelers, eager to enjoy the idyllic beaches, charming shops, and lively option that Oak Bluffs has to offer. With temperatures typically ranging from the mid-60s to mid-80s Fahrenheit, the warm weather creates great conditions for outdoor activities like biking along the scenic coastline or exploring the picturesque Martha's Vineyard.

During these peak months, visitors can take part in the local culture, attending events like the famous Oak Bluffs Carnival or enjoying fresh seafood at beachfront restaurants. The bustling energy of fellow travelers enhances the experience, making it an ideal time for those seeking a lively vacation.

If you are looking for a more budget-friendly option, consider visiting in November. While the summer crowds dissipate, you can still appreciate the beauty of Oak Bluffs, with fewer tourists and the stunning fall landscape providing a serene backdrop for leisurely strolls along the shore.

Ultimately, whether you prefer the excitement of peak summer activities or the tranquility of the off-season, Oak Bluffs offers delightful experiences year-round.
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, Massachusetts, United States of America?
In Oak Bluffs, visitors can enjoy a variety of attractions that highlight the area's unique charm. The vibrant Oak Bluffs Harbor is a focal point, offering beautiful views and a lively option with restaurants and shops nearby. The historic Gingerbread Cottages are a must-see, showcasing colorful Victorian architecture that adds to the town's character.

For those seeking outdoor activities, the nearby beaches, such as Inkwell Beach, provide opportunities for swimming and sunbathing, while the scenic Ocean Park offers a lovely green space for picnics and leisurely strolls. The local arts scene is reflected in the Martha's Vineyard Camp Meeting Association, where events and community gatherings often take place.

Additionally, visitors can take advantage of the town's proximity to the ferry terminal, making it easy to explore other parts of Martha's Vineyard, including Edgartown and Vineyard Haven.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the 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 as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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