Oak Bluffs holiday lettings

We found 1,986 holiday rentals — enter your dates for availability

Select from 260 houses, 40 flats and other holiday rentals to find the perfect place for your stay in Oak Bluffs. 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:17 Oct - 24 Oct

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.

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.

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

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.

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?
Among the most sought-after neighbourhoods to get a holiday property in Oak Bluffs is Lagoon Heights. Find your perfect stay on Vrbo and experience this area just like a local.
What is the most popular type of holiday rental accommodation in Oak Bluffs?
The most desirable types of holiday rentals in Oak Bluffs are houses. After something a little different? Vrbo has a variety of options to match our guests' requirements, so you'll see holiday homes in all shapes and sizes. The ideal fit is waiting for you --- snap up yours today.
How much does it cost to rent a holiday rental in Oak Bluffs?
The average price for a holiday rental in Oak Bluffs is determined by a number of factors, like length of stay, property type and season. Whether you're thinking about a sprawling villa with space for extended family or an apartment for just you and the kids, just add your dates of travel to find stays that offer great value.
How much does it cost to rent a beach house in Oak Bluffs?
The average price for a holiday rental near the beach in Oak Bluffs depends on when you're visiting the area and the style and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering your dates of travel. Then use our filters to choose the number of bedrooms and amenities that you require, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday rentals in Oak Bluffs?
With 310 holiday rentals that welcome four-legged guests, your furry buddy can also come along on your Oak Bluffs holiday. Use the filter tool to browse our pet-friendly holiday rentals and find a holiday home that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Oak Bluffs?
Pack your swimwear and inflatable unicorn, because there are 67 houses with a private pool in Oak Bluffs. Unwind at one of these terrific holiday rentals and every day can be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Oak Bluffs?
When it comes to rental amenities that guests are looking for in Oak Bluffs, tennis, a firepit and a chef are at the top of the list. With Vrbo holiday homes, you'll find options to fit your style and taste, whether you're going on a holiday with your partner, family members or even pets.
Are there large group holiday rentals in Oak Bluffs?
You'll find 62 holiday rentals in Oak Bluffs that can host 10 or more people. Whether you're organising a get-together with extended family or a celebration like a birthday, there's ample space to get your group together under the same roof.
Are there holiday rentals in Oak Bluffs that welcome kids?
Bring the entire group together for a fun-packed adventure in Oak Bluffs at one of our 310 family-friendly holiday properties. These stays provide conveniences that are just perfect for getaways with children, such as full kitchens, living rooms and patios. Just click on the "Properties good for families" filter box and pick out your favourite.
What are the top attractions for families in Oak Bluffs?
Keeping the kids happy during your Oak Bluffs holiday is child's play with these top family-friendly attractions:

  • Inkwell Beach
  • Oak Bluffs Town Beach
  • Falmouth Heights Beach

Are there one-bedroom holiday rentals in Oak Bluffs?
There are 30 one-bedroom properties in Oak Bluffs to select from. A one-bedroom holiday rental is a great choice if it's only you and your partner or if you're travelling on your own. Add in more convenience, privacy and space compared to a hotel, and you've got the makings of a break to remember.
Can I find two-bedroom holiday rentals in Oak Bluffs?
Gather your loved ones and experience complete comfort and privacy in one of the 59 two-bedroom holiday rentals Oak Bluffs has to offer.
Are there holiday rentals with WiFi in Oak Bluffs?
Whether you want to keep up with the headlines, make a video call or surf social media, there are 89 holiday homes with WiFi in Oak Bluffs. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Oak Bluffs?
There are 280 Vrbo holiday homes with air conditioning in Oak Bluffs providing that gentle, cool breeze and extra bit of comfort. Enter your preferred travel dates and then take advantage of our filters to find stays with air conditioning.
How old do you have to be to rent a holiday rental in Oak Bluffs?
The age limit can differ across properties on Vrbo, so be sure to check the rules of the holiday home in Oak Bluffs you're considering. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Oak Bluffs for?
The amount of time you can stay in an Oak Bluffs holiday rental for depends on each property. Just tap in your preferred travel dates to see options that offer long-term stays. They come with everything you need to make your extended trip more comfortable and convenient, such as kitchens and yards. Some holiday homes may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

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