Oak Bluffs holiday lettings

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.

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 Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.1°F (1.7°C)	Light Rain	Mostly Sunny	Average	Moderately Low
February	35.1°F (1.7°C)	Light Rain	Mostly Cloudy	Average	Moderately Low
March	38.8°F (3.8°C)	Light Rain	Mostly Sunny	Average	Moderately Low
April	46.4°F (8.0°C)	Light Rain	Mostly Sunny	Average	Average
May	54.5°F (12.5°C)	Light Rain	Mostly Sunny	Average	Average
June	63.0°F (17.2°C)	Light Rain	Mostly Sunny	High	Moderately High
July	71.1°F (21.7°C)	Light Rain	Mostly Sunny	High	Moderately High
August	71.6°F (22.0°C)	Light Rain	Mostly Sunny	High	Moderately High
September	66.6°F (19.2°C)	Light Rain	Mostly Sunny	Average	Average
October	58.5°F (14.7°C)	Light Rain	Mostly Sunny	Low	Average
November	48.9°F (9.4°C)	Light Rain	Mostly Sunny	Low	Average
December	41.4°F (5.2°C)	Light Rain	Mostly Sunny	Low	Average

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)
• Farm Neck Golf Club (1.2 mi / 2 km)
• Cape Cod Winery (8.6 mi / 13.8 km)
• Cape Cod Country Club (11.5 mi / 18.5 km)
• Stand Up & Paddle Cape Cod (15.1 mi / 24.3 km)
• Fulling Mill Brook Preserve (9.7 mi / 15.6 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.