Oak Bluffs holiday lettings

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

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

Image gallery for Cape Cod (New Seabury) Family Compound private pool near beach/dining/shopping

Beautiful courtyard with private pool and bar
9.8 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)

Cape Cod (New Seabury) Family Compound private pool near beach/dining/shopping

Mashpee

11% off
Price is £5,808
for 7 nights, 1 home
£830 per night
includes taxes & fees
Cape Cod (New Seabury) Family Compound private pool near beach/dining/shopping

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

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

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

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

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

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

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

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

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

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

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

The town's vibrant nightlife can be experienced at local bars and live music venues, particularly during the summer months when the atmosphere becomes lively with events and gatherings.
Can I change or cancel my Oak Bluffs home rental booking on Vrbo?
To find Oak Bluffs 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Oak Bluffs 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.
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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

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

More holiday ideas