Oak Bluffs vacation rentals

We found 1,842 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:Jun 12 - Jun 19

Image gallery for Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.

Exterior
9.8 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)

Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.

East Falmouth

8% off
Price is $815
$5,705 for 7 nights
All fees included
Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.

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Find out more about Oak Bluffs

Why visit Oak Bluffs

  • Beautiful Beaches: Oak Bluffs boasts stunning beaches where visitors can relax and enjoy the ocean views.
  • Historic Lighthouse: The iconic lighthouse is a must-see, offering a glimpse into the town's rich maritime history.
  • Charming Local Culture: Experience the vibrant culture with local shops, art galleries, and community events.
  • Scenic Ferry Rides: Take a ferry to explore nearby islands and enjoy breathtaking views along the way.
  • Cozy Accommodation: Choose from a variety of vacation rentals, from charming cottages to stylish condos.

Popular types of accommodation in Oak Bluffs

Planning a getaway to Oak Bluffs? You're in for a treat. This charming destination offers a variety of vacation rentals, including private homes, cozy cottages, and stylish condos. Whether you're seeking a serene retreat or a lively vacation spot, you’ll find the perfect home for rent. Explore the best Oak Bluffs vacation rentals and Vineyard vacation rentals to make your trip memorable and filled with comfort.

  • Houses: These are the top choice for travelers in Oak Bluffs, ideal for families and groups seeking a spacious, home-like atmosphere.
  • Cottages: A close second, cottages offer a quaint and cozy setting, perfect for romantic getaways or peaceful retreats.
  • Condos: Popular among visitors, condos provide modern amenities and often stunning views, making them a great option for convenience.
  • Apartments: Apartments are a practical choice for those looking for comfortable, self-catering accommodations in the heart of the action.
  • Cabins: While less common, cabins offer a charming escape into nature, perfect for outdoor enthusiasts.**

Top attractions in and around Oak Bluffs

Oak Bluffs, Massachusetts, is an ideal destination for beach lovers and outdoor enthusiasts. Visitors can explore beautiful beaches, take a ferry to nearby islands, and admire the historic lighthouse. The town's attractions cater to travelers seeking a blend of culture and scenic experiences, making it a perfect spot for a memorable vacation. Whether you're traveling solo, with family, or friends, Oak Bluffs offers a delightful escape filled with natural beauty and rich history.

  • Inkwell Beach: Known for its vibrant beach vibes, Inkwell Beach is a popular spot in Oak Bluffs. This picturesque beach offers soft sands and a lively atmosphere, perfect for sunbathing, swimming, and enjoying the local community.
  • Woods Hole Ferry Terminal: Located 7 miles away, this ferry terminal serves as a gateway to Martha's Vineyard and nearby islands. It provides scenic views and easy access to exciting adventures across the waters.
  • Oak Bluffs Harbor: Nestled within Oak Bluffs, this charming harbor boasts stunning scenery and beach vibes. It's ideal for leisurely strolls, waterfront dining, and watching boats come and go.

Things to do recommended for couples

For a romantic getaway in Oak Bluffs, consider a round of golf at the luxurious Cape Cod Country Club, just 11 miles away, or enjoy the serene atmosphere at Twin Brooks Golf Course, located 19 miles from town. Both offer a perfect setting for couples to unwind together.

Things to do recommended for families

Families will delight in the charming Carousel, a historic merry-go-round, and explore the beautiful beaches at Oak Bluffs. Don't miss the colorful Gingerbread Cottages for a perfect photo opportunity and enjoy a bike ride along the scenic paths for a fun-filled day outdoors.

Things to do recommended for groups

Groups visiting Oak Bluffs can enjoy a scenic bike ride along the beautiful coastline, relax at the iconic flying horses carousel, and explore the charming gingerbread cottages. Don't miss a group tour of Martha's Vineyard to experience local culture and delicious seafood dining options.

*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 planning your trip—whether you’re traveling with a group, family, pets, or seeking extended stays—be sure to prioritize your preferences in the search filters. 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 full kitchen or outdoor area for group gatherings. Fortunately, Vrbo allows you to filter for these options and many more.
  • Traveling to Oak Bluffs with young kids: Traveling with young children can present its own set of challenges. 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 vacation isn’t truly a getaway without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer amenities like food bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oak Bluffs: If you're interested in vacation rentals with special rates 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 rental options. Don't forget to include features 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, offers a delightful blend of beach relaxation and scenic views. Visitors can enjoy the charming town beach, breathe in the refreshing ocean air, and soak in exceptional ocean vistas. The friendly atmosphere and recreational opportunities make it an ideal spot for a laid-back getaway. Explore the vibrant local culture and discover the beauty of nearby towns, ensuring a memorable vacation experience filled with stunning scenery.

  • Martha's Vineyard: A picturesque island located 7 miles from Oak Bluffs, Martha's Vineyard is renowned for its stunning beaches and breathtaking outdoor scenery. Visitors flock to this idyllic destination to soak up the sun on family-friendly beaches, hike scenic trails, and enjoy vibrant local culture. Don’t miss the chance to attend a music concert or relax at one of the luxurious resorts. The island also offers excellent golf courses, making it a perfect spot for both relaxation and recreation. Local landmarks such as the iconic Cape Cod views enhance the charm of this beautiful island.
  • Falmouth: Just 7 miles away from Oak Bluffs, Falmouth is a charming coastal city that draws travelers with its beautiful beaches and outdoor activities. This city is perfect for those seeking a mix of relaxation and adventure, featuring pristine family beaches and a variety of golf courses. Falmouth also offers educational attractions and access to country private clubs, providing a well-rounded experience for visitors. The nearby Cape adds to the scenic allure, making it a fantastic place to explore the natural beauty of Cape Cod.
  • Edgartown: Located only 5 miles from Oak Bluffs, Edgartown is a historic city that captivates visitors with its stunning scenery and beach access. Known for its upscale shopping areas and beautiful golf courses, Edgartown offers a blend of leisure and luxury. Travelers can enjoy relaxing at family beaches or exploring the charming streets lined with quaint shops and eateries. With its picturesque landscapes and proximity to the coast, Edgartown is an essential stop for anyone looking to experience the best of 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 SunnyAverageModerately Low
February35.1°F (1.7°C)Light RainMostly CloudyAverageModerately Low
March38.8°F (3.8°C)Light RainMostly SunnyAverageModerately 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 SunnyHighModerately High
July71.1°F (21.7°C)Light RainMostly SunnyHighModerately High
August71.6°F (22.0°C)Light RainMostly SunnyHighModerately 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

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your needs.

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 certainly has its rewards. Join our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash on eligible stays. Sign up now and begin earning.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly area where you can easily plan new trips, continue from where you last stopped, or manage your travel arrangements. You'll see the properties you've saved or booked neatly organized under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: 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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