Oak Bluffs holiday lettings

We found 1,881 holiday rentals — enter your dates for availability

Discover a selection of 261 homes, 31 apartments and other holiday rentals in Oak Bluffs that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as parking and a hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Oak Bluffs

Showing deals for:16 Jan - 23 Jan

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

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

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

Edgartown, MA

8% off
Price is £15,616
for 7 nights, 1 room
£2,231 per night
includes taxes & fees
Stunning compound steps to Katama Bay, heated pool, dock & amenities

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Oak Bluffs

  • Picturesque Harbour: Explore the charming Oak Bluffs Harbour, perfect for a leisurely stroll and stunning views.
  • Beautiful Beaches: Relax on the sandy shores of Oak Bluffs Town Beach, ideal for sunbathing and swimming.
  • Historic Landmarks: Discover the area's rich culture through its historic lighthouses and quaint streets.
  • Outdoor Activities: Enjoy kayaking and other outdoor adventures in the tranquil waters surrounding the town.
  • Charming Accommodations: Choose from a variety of holiday rentals, including cosy cottages and modern condos.

Popular types of accommodation in Oak Bluffs

You've chosen Oak Bluffs for your getaway, and now the excitement begins – selecting the perfect accommodation. Discover the most sought-after options for your stay, including houses, charming cottages, and modern condos. With a variety of Oak Bluffs holiday rentals available, you’re sure to find the ideal base for your adventures. Explore your options for Oak Bluffs vacation rentals today!

  • Houses: The top choice for visitors to Oak Bluffs, offering spacious and comfortable stays perfect for families or groups.
  • Cottages: A lovely option for those seeking a quaint and charming retreat, ideal for a romantic getaway or peaceful escape.
  • Condos: A popular accommodation type that combines convenience with modern amenities, perfect for a relaxed holiday experience.
  • Apartments: A versatile choice providing all the comforts of home, suitable for solo travellers or couples.
  • Cabins: A delightful option for nature enthusiasts, offering a rustic atmosphere amidst stunning surroundings.**

Top attractions in and around Oak Bluffs

Oak Bluffs promises a delightful vacation filled with beachside relaxation and outdoor adventures. Visitors can explore the picturesque Oak Bluffs Harbour and unwind on its beautiful beaches. The area is rich in culture, featuring historic lighthouses and charming streets, making it an ideal destination for those seeking scenic views and engaging experiences. Whether you’re travelling solo, with family, or as a couple, Oak Bluffs offers something for everyone.

  • Inkwell Beach: A vibrant beach located in Oak Bluffs, Inkwell Beach is known for its lively atmosphere and stunning views. Perfect for sunbathing, swimming, or enjoying a leisurely stroll along the shore, it’s a quintessential seaside experience.
  • Martha's Vineyard Museum: Situated 1.2km from Oak Bluffs, this museum offers a rich insight into the island's history and culture. Explore fascinating exhibits that showcase maritime heritage and local artistry, immersing yourself in the unique story of Martha's Vineyard.
  • Circuit Avenue: A bustling street in Oak Bluffs, Circuit Avenue is lined with charming shops, restaurants, and vibrant nightlife. Experience the lively city vibes while exploring local boutiques and enjoying delicious cuisine in this lively hub.

Things to do recommended for couples

For a romantic getaway in Oak Bluffs, indulge in a round of mini-golf at Island Cove Adventures, just 1.9km away. Alternatively, enjoy the luxury vibes at Cape Cod Country Club, located 6.8km from town. Both offer delightful experiences for couples seeking adventure and charm.

Things to do recommended for families

During your family holiday in Oak Bluffs, enjoy a delightful ride on the Flying Horses Carousel, embrace nature at the serene Fulling Mill Brook Preserve, and explore the tranquil Mashpee River Reservation for relaxation and wellness activities. A perfect blend of fun and tranquillity awaits!

Things to do recommended for groups

In Oak Bluffs, groups can enjoy a film at the Martha's Vineyard Film Center for a cultural experience, play a round of golf at the scenic Farm Neck Golf Club, or cycle along the picturesque Shining Sea Bikeway, perfect for outdoor enthusiasts.

What do I need to keep in mind when booking a vacation in 'Oak Bluffs

When travelling with a group, family, or pets, or if you're seeking longer stays, it's important to filter your options according to your specific needs. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Oak Bluffs with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas suitable for group gatherings. Thankfully, you can easily filter for all these options, and much more, on Vrbo.
  • Traveling to Oak Bluffs with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Oak Bluffs: For many, a family holiday isn’t truly complete without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Oak Bluffs: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect 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, offers a delightful blend of scenic beauty and outdoor activities, making it an ideal destination for a relaxing beach holiday. Visitors can unwind at the Oak Bluffs Town Beach, explore the charming neighbourhoods, or enjoy kayaking adventures in the tranquil waters. The friendly atmosphere and picturesque surroundings create an inviting experience for all who venture here, ensuring unforgettable moments in this charming coastal town.

  • Martha's Vineyard: Martha's Vineyard is a picturesque island located 4.3km from Oak Bluffs. Known for its stunning outdoor scenery and pristine beaches, it offers a delightful escape for nature lovers. Visitors can partake in various activities, including music concerts and golfing, while enjoying the relaxed island atmosphere. Key attractions include beautiful family-friendly beaches and tranquil lakes, perfect for leisurely days in the sun. The charming towns on the island, with their quaint shops and restaurants, add to the overall experience, making Martha's Vineyard a must-visit destination.
  • Falmouth: Situated 4.3km from Oak Bluffs, Falmouth is a vibrant town that beckons visitors with its beautiful outdoor spaces and inviting beaches. Known for its scenic views, Falmouth is ideal for beachgoers and outdoor enthusiasts alike. Popular activities include enjoying the golf courses and exploring the local private country clubs. Attractions such as family-friendly beaches and the stunning Cape Cod coastline are easily accessible, providing endless opportunities for relaxation and adventure. Falmouth combines the charm of a coastal town with a rich variety of experiences to make your visit unforgettable.
  • Edgartown: Just 3.1km from Oak Bluffs, Edgartown is a charming town that showcases the classic New England coastal experience. With its beautiful beaches and scenic landscapes, it attracts travellers seeking outdoor adventures and relaxation. Visitors can enjoy golfing at local courses and family-friendly beach outings. The town is known for its historic architecture and lovely waterfront views, making it perfect for leisurely strolls. Edgartown's unique blend of natural beauty and rich history provides a delightful backdrop 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

Are you hoping to keep costs down on your next getaway? It might be worth considering some flexibility with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform to help you plan new journeys, resume your previous arrangements, or manage your travel plans with ease. You can easily view and organise your saved or booked properties, which are conveniently sorted into Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/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 well known for its beaches, shopping and local tours. With a holiday 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 hoping to find attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that makes Oak Bluffs a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

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

Exploring the natural landscape of Oak Bluffs

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Oak Bluffs is a great place to get outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

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

Seasonal weather in Oak Bluffs

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 20°C.

Transport 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 centre. 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 holiday rental?
When considering a holiday rental in Oak Bluffs, the East Chop neighbourhood is an excellent choice. This picturesque area is renowned for its stunning coastal views and charming Victorian architecture, making it a delightful spot for a getaway. East Chop is home to the iconic East Chop Lighthouse, which offers a lovely backdrop for photos and a glimpse into the area's maritime history. Additionally, the nearby beaches provide plenty of opportunities for relaxation and water activities.

Another fantastic area to consider is the Oak Bluffs Harbour district. This vibrant waterfront area boasts a lively atmosphere, characterised by its array of shops, restaurants, and art galleries. Visitors can enjoy a leisurely stroll along the harbour, where they can admire the colourful Gingerbread Cottages, a unique feature of the town. The proximity to the ferry terminal also makes this location convenient for those arriving from the mainland.
How much does it cost to rent a holiday home in Oak Bluffs?
Prices for holiday 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 holiday 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 along East Chop is particularly desirable. This scenic neighbourhood features stunning views of the ocean and is known for its charming Victorian cottages. Many beach houses in this region come equipped with amenities such as large decks for outdoor dining, beach access, and spacious living areas ideal for families or groups.

Another excellent option is the vicinity near Oak Bluffs Town Beach, where you can find properties that are just a short stroll from the sandy shores. These rentals often include conveniences like outdoor showers, private patios, and fully equipped kitchens, making them great for a relaxing beach holiday. The proximity to local shops, restaurants, and the famous Oak Bluffs Carousel adds to the appeal, providing plenty of entertainment options for visitors.
What is the most popular type of holiday rental accomodation in Oak Bluffs?
In Oak Bluffs, holiday houses are the most popular type of accommodation, with around 236 available across the charming neighbourhoods close to the waterfront and scenic beaches. These houses typically offer spacious layouts, multiple bedrooms, fully equipped kitchens, and often outdoor areas such as patios or decks for enjoying the pleasant summer weather.
Are there any family house rentals in Oak Bluffs?
In Oak Bluffs, Massachusetts, there is a substantial selection of family-friendly house rentals available, with around 226 properties to choose from. This charming town on Martha's Vineyard is well-known for its picturesque beaches and vibrant community atmosphere, making it an ideal spot for family holidays.

Visitors can find homes that offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to play. Many rentals also come with amenities such as air conditioning and Wi-Fi, ensuring a comfortable stay for everyone.

The locale is close to popular attractions, including the iconic Gingerbread Cottages and Oak Bluffs Campground, which provide a delightful glimpse into the area's history and culture. Additionally, families can enjoy nearby beaches like Inkwell Beach, where kids can swim and build sandcastles, or explore the scenic bike paths that wind through the island.
Can I rent a holiday home with a pool or hot tub in Oak Bluffs?
In Oak Bluffs, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 68 options to choose from. This charming town on Martha's Vineyard is known for its picturesque beaches, vibrant gingerbread cottages, and lovely waterfront views. Many of the rental properties come equipped with private pools, hot tubs, and spacious outdoor areas, great for relaxing after a day of exploring the island.
Can I find long-stay holiday rentals in Oak Bluffs?
A long-stay holiday 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 numerous pet-friendly house rentals available, with around 80 options to choose from. Many of these properties offer a variety of amenities, such as fully equipped kitchens, spacious living areas, and outdoor spaces like decks or patios superb for enjoying the pleasant coastal climate.
Are there any remote work holiday rentals in Oak Bluffs?
In Oak Bluffs, there are numerous remote work holiday rentals available, with around 337 options to choose from. This charming town on Martha's Vineyard is great for those looking to balance work and leisure. Many properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desks, and comfortable office chairs, ensuring a productive environment. Additionally, some rentals offer features such as laptop workspaces and even computer monitors for added convenience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oak Bluffs holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday 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 holiday rental?
The best time to visit Oak Bluffs for a holiday rental is during the vibrant summer months, particularly in July. This peak season, which spans from June to August, draws numerous travellers seeking sun-soaked days and the charm of Martha's Vineyard. Visitors will find a delightful mix of outdoor activities, from relaxing on the picturesque beaches to exploring the quaint streets lined with colourful gingerbread cottages.

July offers warm temperatures, typically in the high 20s Celsius, making it ideal for enjoying the stunning coastal scenery and participating in water sports. The lively atmosphere during this period ensures plenty of opportunities to mingle with fellow holidayers, attend local events, and savour fresh seafood at various eateries.

For those looking for a more budget-friendly option, November presents a wonderful opportunity to experience Oak Bluffs in a quieter setting. While the weather may be cooler, averaging around 10°C, the off-season allows for peaceful walks along the beach and the chance to appreciate the natural beauty without the crowds.
How early should I book a Oak Bluffs holiday rental?
Book your Oak Bluffs holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oak Bluffs?
In Oak Bluffs, visitors can enjoy a variety of attractions that showcase the area's charm and natural beauty. The vibrant Oak Bluffs Harbour is a picturesque spot, great for leisurely strolls and offers access to ferry services. Nearby, the iconic Gingerbread Cottages, with their colourful Victorian architecture, provide a unique glimpse into the town's history and are a favourite for photographers.
Can I change or cancel my Oak Bluffs home rental booking on Vrbo?
To find Oak Bluffs holiday 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 holiday 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.

More holiday ideas