Oak Bluffs vacation rentals

Why visit Oak Bluffs

• Stunning beaches: Oak Bluffs boasts beautiful sandy shores perfect for sunbathing and relaxation.
• Charming architecture: Explore historic homes and picturesque streets that reflect the town's unique character.
• Outdoor activities: Engage in various recreational pursuits, from biking to hiking, amidst scenic landscapes.
• Historic lighthouses: Visit iconic lighthouses that offer stunning views and a glimpse into maritime history.
• Welcoming community: Experience the friendly atmosphere and local culture that make Oak Bluffs a delightful destination.

Popular types of accommodation in Oak Bluffs

If you're exploring options for your stay in Oak Bluffs, we have you covered. The most popular types of holiday rentals here include private holiday homes, cozy cottages, and modern condos. Whether you're seeking a spacious house rental for the whole family or a charming getaway for two, Oak Bluffs offers a variety of holiday rentals that cater to your needs, ensuring a memorable experience while you soak in the beauty of this lovely destination.

• Private Holiday Homes: The most sought-after option for visitors in Oak Bluffs, offering spacious accommodations ideal for families or groups.
• Cottages: Charming and cozy, these quaint dwellings provide a quintessential New England experience for a relaxing getaway.
• Condos: Convenient and modern, condos are perfect for those seeking comfort with amenities close to the beach.
• Apartments: A practical choice for individuals or couples, providing a home-like atmosphere with essential facilities.
• Cabins: Rustic and inviting, cabins offer a unique retreat surrounded by nature for a peaceful holiday experience.**

Top attractions in Oak Bluffs

Oak Bluffs offers a delightful holiday experience with its stunning beaches, outdoor activities, and picturesque scenery. Visitors can explore historic lighthouses and charming streets while immersing themselves in the local culture. Whether you're seeking relaxation on the beach or adventure in nature, Oak Bluffs has something for every traveller looking to enjoy a vibrant coastal getaway.

• Inkwell Beach: This charming beach offers a laid-back atmosphere with soft sand and gentle waves, perfect for sunbathing and swimming. The vibrant beach vibes create a welcoming environment for families and friends to relax and enjoy the seaside.
• Oak Bluffs Harbor: Stroll along the picturesque harbor, where stunning scenery meets the tranquil waters. It's an ideal spot for enjoying fresh sea air, watching boats, and soaking up the coastal beauty.
• Circuit Avenue: Experience the lively energy of this bustling street filled with eclectic shops, eateries, and local art. The city vibes make it a great place for shopping and dining while immersing yourself in the local culture.

Things to do recommended for couples

Discover the charm of Oak Bluffs with a romantic stroll along the picturesque waterfront, or enjoy a sunset sail on the tranquil waters. Don't miss the enchanting gingerbread cottages, perfect for a cozy photo op, and indulge in a delightful dinner at a local seafood restaurant for a memorable evening together.

Things to do recommended for families

Families visiting Oak Bluffs can enjoy a day at the stunning beaches, explore the iconic Gingerbread Cottages, and take a ride on the Flying Horses Carousel. Don’t miss the opportunity for a scenic bike ride through the beautiful landscapes of Martha’s Vineyard.

Things to do recommended for groups

Groups visiting Oak Bluffs can enjoy a scenic bike ride along the picturesque coastline, explore the charming gingerbread cottages in the Tabernacle area, and relax on the beautiful beaches. Don't miss the vibrant Oak Bluffs Marina for a lovely afternoon stroll and local dining options.

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

When you're planning a trip, whether it's with a group, family, pets, or for an extended stay, be sure to set your priorities with the right filters. Here are some helpful Vrbo booking tips to guide you.

• Traveling to Oak Bluffs with a group: Think about how many bedrooms you'll require, along with features like a complete 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: Traveling with young children can present its challenges. It's essential to prioritize their comfort and safety, along with 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 getaway isn't truly complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Oak Bluffs: If you're in search of vacation rentals offering discounts for stays of a month or more, 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 consider including features like a parking spot, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Oak Bluffs

Oak Bluffs, Massachusetts, is a charming coastal destination perfect for a relaxing getaway. With its stunning beaches and picturesque scenery, visitors can immerse themselves in the vibrant atmosphere of friendly locals and outdoor recreation. Explore the elegant homes and exceptional views that define this lovely town. Whether you're soaking up the sun or enjoying leisurely strolls, Oak Bluffs promises a memorable holiday experience surrounded by natural beauty and inviting vibes.

• Martha's Vineyard: This picturesque island, located 11km from Oak Bluffs, is renowned for its stunning beaches and breathtaking scenery. Visitors flock to Martha's Vineyard for its outdoor activities, including beach days and scenic hikes. The island is a cultural hub with lively music concerts and various resort options. You can explore its charming towns, relax on family-friendly beaches, or take in the captivating vistas of the Cape, making it an ideal destination for nature lovers and families alike.
• Falmouth: Situated 11km from Oak Bluffs, Falmouth is a vibrant city that offers a delightful blend of coastal charm and outdoor adventure. Known for its beautiful beaches and scenic landscapes, Falmouth is perfect for those looking to enjoy sun-soaked days by the water. Popular activities include golf and visits to local education centres, ensuring a well-rounded experience. The area is dotted with family-friendly beaches and majestic Cape views, making it a great spot for family outings and leisurely strolls along the shore.
• Edgartown: Just 8km from Oak Bluffs, Edgartown is a charming city known for its rich maritime history and stunning coastal scenery. Visitors can enjoy outdoor activities such as golfing and shopping in its quaint downtown area. Edgartown offers a unique blend of upscale boutiques and local eateries, perfect for a leisurely day out. With its beautiful family-friendly beaches and picturesque views of the Cape, it’s an inviting destination for those seeking relaxation and exploration.

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 hoping to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices can fluctuate. Additionally, consider booking a longer stay to enjoy considerable savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of holiday rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, manage your ongoing arrangements, or review and organize your bookings. Your saved or booked properties are organized into categories: Potential, Upcoming, or Current Trips, making it easy to keep everything in order. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/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 known for its beaches, shopping and local tours. With a vacation 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 looking for top things to see and do in the city? Venture out of your cozy vacation rental and experience everything that makes Oak Bluffs a fun place to get away. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

• Farm Neck Golf Club (1.2 mi / 2 km)
• Shining Sea Bikeway (9.2 mi / 14.8 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 take in the scenery, Oak Bluffs is a great place to get outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

• 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)
• Lambert's Cove Beach (5.6 mi / 9.1 km)
• Menauhant Beach (6.4 mi / 10.3 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 68°F.

Transportation 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 center. 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.