Oak Bluffs holiday lettings

We found 1,938 holiday rentals — enter your dates for availability

Discover a selection of 270 homes, 36 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:2 Oct - 9 Oct

Image gallery for THE PARK ESTATE! Your Martha's Vineyard Getaway!

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9.8 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)

THE PARK ESTATE! Your Martha's Vineyard Getaway!

Oak Bluffs

8% off
Price is £43,429
for 7 nights, 1 home
£6,204 per night
includes taxes & fees
THE PARK ESTATE! Your Martha's Vineyard Getaway!

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Why visit Oak Bluffs

  • Stunning Beaches: Enjoy the golden sands and refreshing waters at Oak Bluffs Town Beach, perfect for sunbathing and swimming.
  • Unique Architecture: Admire the vibrant gingerbread cottages that showcase the town's distinctive and charming architectural style.
  • Historic Lighthouse: Explore the historic lighthouse, offering picturesque views and a glimpse into Oak Bluffs' maritime heritage.
  • Outdoor Activities: Engage in various outdoor pursuits, including cycling, hiking, and water sports, amidst beautiful scenery.
  • Iconic Attractions: Visit the famous Flying Horses Carousel, a delightful experience for visitors of all ages.

Popular types of accommodation in Oak Bluffs

Discover the charm of Oak Bluffs, Massachusetts, where vibrant gingerbread cottages and stunning waterfront views await. This delightful city offers a range of attractions, including the iconic Flying Horses Carousel and beautiful beaches. For your stay, consider our popular vacation rentals, featuring private homes, cosy cottages, and comfortable condos. Experience the perfect getaway with transparency, savings, and reassurance as you explore the unique delights of Oak Bluffs.

  • Private Holiday Homes: The most sought-after accommodation in Oak Bluffs, offering spacious and comfortable living tailored for families and groups.
  • Cottages: Charming and quaint, these cosy retreats provide a perfect blend of rustic charm and modern convenience.
  • Condos: Stylish and often centrally located, these contemporary spaces are ideal for those seeking a vibrant atmosphere.
  • Flats: Convenient and practical, these self-contained units are perfect for couples or solo travellers.
  • Cabins: A delightful option for those looking to immerse themselves in nature, providing a serene getaway.**

Top attractions in and around Oak Bluffs

Oak Bluffs, Massachusetts, is a charming seaside town perfect for beach lovers and outdoor enthusiasts. Visitors can enjoy stunning beaches, explore the historic lighthouse, and stroll along picturesque streets. The area offers myriad outdoor activities, from cycling and hiking to water sports, ensuring a memorable experience for those seeking both culture and adventure. With its scenic beauty and rich history, Oak Bluffs is an ideal destination for a delightful vacation.

  • Inkwell Beach: A picturesque beach known for its vibrant atmosphere and stunning views. Ideal for sunbathing, swimming, and relaxing, it offers a quintessential seaside experience.
  • Circuit Avenue: The bustling heart of Oak Bluffs, Circuit Avenue is lined with charming shops, eateries, and galleries, perfect for enjoying the local culture and vibrant city vibes.
  • Martha's Vineyard Preservation Trust Historic Buildings: A collection of beautifully preserved historic structures that showcase the rich history and cultural heritage of Martha's Vineyard, providing a fascinating glimpse into the past.

Things to do recommended for couples

Experience romance in Oak Bluffs with a sunset stroll along the picturesque Harbour, followed by a scenic bike ride through the charming gingerbread cottages. Enjoy a candlelit dinner at a local seafood restaurant, and don’t miss the enchanting views from the iconic Flying Horses Carousel.

Things to do recommended for families

Families will delight in the charm of Oak Bluffs, exploring the scenic beaches and the historic gingerbread cottages. Enjoy a fun-filled day at the Flying Horses Carousel, the oldest operating carousel in the U.S., or take a leisurely bike ride along the picturesque coastal paths.

Things to do recommended for groups

Groups visiting Oak Bluffs can enjoy a charming stroll along the colourful Gingerbread Cottages, indulge in fresh seafood at local eateries, and take a scenic bike ride along the picturesque coastline. Don't miss a sunset at the beach or a visit to the vibrant Oak Bluffs Campground.

*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

If you’re travelling with a group, family, or pets, or if you’re interested in extended stays, it’s important to apply the right filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Oak Bluffs with a group: Take into account the number of bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Oak Bluffs with young kids: Travelling with young children can be quite demanding. It is essential to prioritise their comfort and safety, along with ensuring that there are 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, a family holiday isn’t truly complete without their four-legged companion by their side. If you can relate to this, explore the 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 longer, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include 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 relaxation for visitors. Stroll along the charming Oak Bluffs Town Beach, where golden sands meet refreshing waters, perfect for a day of sunbathing or swimming. Explore the vibrant gingerbread cottages that adorn the area, showcasing unique architecture. With its friendly atmosphere and outdoor recreational options, Oak Bluffs promises a memorable getaway filled with picturesque views and tranquil experiences.

  • Martha's Vineyard: A picturesque island located 11km from Oak Bluffs, Martha's Vineyard is renowned for its stunning beaches and enchanting outdoor scenery. Visitors flock here to enjoy the tranquillity of family-friendly beaches, explore charming seaside towns, and partake in vibrant music concerts. The island is also home to luxurious resorts and beautiful golf courses, offering a perfect blend of relaxation and recreation. Don't miss the iconic lighthouses and captivating coastal views that make Martha's Vineyard a must-visit destination.
  • Falmouth: Situated 11km from Oak Bluffs, Falmouth is a delightful coastal city that attracts those seeking beachside relaxation and outdoor adventures. With its scenic beaches and lush landscapes, Falmouth is perfect for family outings and leisurely strolls. The city is well-known for its golf courses and private country clubs that cater to enthusiasts and novices alike. Explore the charming downtown area, where you'll find educational institutions and local shops that showcase the unique character of this lovely seaside town.
  • Edgartown: Just 8km away from Oak Bluffs, Edgartown is a quaint city steeped in maritime history, known for its beautiful beaches and vibrant shopping areas. Visitors can enjoy a day of golfing or explore the numerous boutiques and galleries that line the streets. Edgartown’s stunning coastal landscape is ideal for outdoor activities, making it a favourite spot for families. Be sure to visit the historic whaling captain's houses and the scenic Martha's Vineyard coastline while soaking in the charming atmosphere of this enchanting destination.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 eager to save on your next getaway? We recommend being flexible with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo accommodation 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 provides a convenient area for you to plan new journeys, refine your existing arrangements, or review and manage your bookings. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about 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)
  • Mashpee River Reservation (13.2 mi / 21.2 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.

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