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Oak Bluffs, MA place to stay
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1282 Lodgings in Oak Bluffs, MA

Best Oak Bluffs, MA lodging with a pool

Among the 1282 accommodations in Oak Bluffs, MA, here are the 4 best ones with a pool

Luxury Log Villa With Endless Pool, Hot Tub & Expansive Grounds - Oak Bluffs, MA
No reviews

Luxury Log Villa With Endless Pool, Hot Tub & Expansive Grounds

house, Edgartown
This luxury log villa is located in Edgartown, offering secluded accommodation on 0.3 hectares of landscaped grounds, within easy cycling distance of Edgartown village, State Beach and local shops.
This four-bedroom, three-bathroom residence accommodates up to eight guests and features an E2000 Endless Pool Swim Spa & Hot Tub, a wood-burning fireplace, a wood-burning stove, extensive outdoor entertaining spaces with a barbecue, and a private outdoor shower.
Privacy & Relaxation On Martha's Vineyard - Oak Bluffs, MA
10 11 reviews

Privacy & Relaxation On Martha's Vineyard

apartment, Tisbury
This six-bedroom Vineyard Haven holiday home, sleeping twelve, is ideally located within 3.2km of Lake Tashmoo, Tisbury Town Beach, and the Vineyard Haven ferry terminal.
The property boasts a private pool, tennis court, spa, and fully equipped kitchen, alongside free Wi-Fi and a DVD player, making it perfect for large families or groups seeking a luxurious self-catering stay.
Privacy On Martha's Vineyard - Oak Bluffs, MA
10 3 reviews

Privacy On Martha's Vineyard

apartment, Tisbury
This six-bedroom, six-bathroom house is located in a peaceful golfing community in Tisbury, under 3.2 kilometres from Vineyard Haven's town centre and ferry services.
The property boasts a large heated swimming pool (52 x 20ft), a lower-level entertainment room, a private garden with a firepit, and accommodates up to twelve guests, offering easy access to a private beach and Mink Meadows Golf Club.
4-br, Hot Tub, Wifi, Ac, Fire Pit. - Oak Bluffs, MA
9.9 57 reviews

4-br, Hot Tub, Wifi, Ac, Fire Pit.

apartment, Oak Bluffs
This spacious five-bedroom house in a quiet Oak Bluffs neighbourhood is situated 3.2 kilometres from Oak Bluffs town centre and the Atlantic Ocean.
The 1.2-acre property boasts a private heated pool (open May 15th - September 7th), hot tub, extensive outdoor amenities including a basketball court, a fully equipped gourmet kitchen, game room with consoles, seven smart TVs, and accommodates up to ten guests.

Best family friendly Oak Bluffs, MA lodging

Among the 1282 accommodations in Oak Bluffs, MA, here are the 4 best for families

Estate With Saltwater Pool, Pond Kayaks Sleeps 12 - Oak Bluffs, MA
No reviews

Estate With Saltwater Pool, Pond Kayaks Sleeps 12

apartment, Oak Bluffs
This expansive estate in Oak Bluffs' Fresh Pond Estates, set within 0.8 kilometres of woodland, offers exceptional privacy while being just 3.2 kilometres from the town's shops, restaurants, Gingerbread Cottages, and Ocean Park, and 152 metres from the bike path.
This family-friendly property accommodates up to 12 guests across a main house and an attached carriage house, boasting a heated saltwater pool, a spa, kayaks, two kitchens, two laundry facilities, and extensive amenities including air conditioning and WiFi, with numerous children's and beach toys provided.
Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path And Town - Oak Bluffs, MA
9.8 57 reviews

Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path And Town

apartment, Oak Bluffs
This family-friendly property is located in Oak Bluffs, just a mile from Farm Neck Golf Club and Oak Bluffs Public Library, and within two miles of Inkwell Beach and Eastville Beach. It has consistently received excellent user ratings.
The house has three bedrooms and two bathrooms, accommodating up to seven guests in its 117 square metres of space. Enjoy the spa tub, garden, and barbecue grills, as well as the fully equipped kitchen, internet, and air conditioning.
️Walking To The Beach️bars And Restaurants - Oak Bluffs, MA
9.8 12 reviews

️Walking To The Beach️bars And Restaurants

apartment, Oak Bluffs
This apartment is located in Oak Bluffs, just a short walk from the bustling harbour and the charming gingerbread cottages. The property has received excellent ratings for its cleanliness, location and overall experience.
The apartment has three bedrooms and three bathrooms, comfortably accommodating up to seven guests. It is equipped with a fully fitted kitchen, a garden, air conditioning, parking, and internet access, ensuring a comfortable and enjoyable stay.
Waterfront Cottage, Downtown W/ Beach - Oak Bluffs, MA
10 129 reviews

Waterfront Cottage, Downtown W/ Beach

apartment, Tisbury
This charming cottage is located in Vineyard Haven, just a short walk from the Martha's Vineyard Chamber of Commerce and Vineyard Haven Terminal. The cottage has received excellent ratings for location, cleanliness, and user experience.
The cottage has one bedroom and can accommodate up to two guests. It features a fully equipped kitchen, two bathrooms, a washing machine, a balcony, a Smart TV, a fireplace, and a private garden.

Frequently asked questions about accommodations in Oak Bluffs, MA

  • What are the must-see sites in or near Oak Bluffs, MA?

    Oak Bluffs is full of charm! You've got to see the iconic gingerbread cottages in the historic district, the Flying Horses Carousel, and the impressive Martha's Vineyard Museum. If you're up for a short drive, the lighthouses at Gay Head and Edgartown are well worth the trip.
  • How can travelers reach Oak Bluffs, MA?

    The easiest way to get to Oak Bluffs is by ferry from Woods Hole or Falmouth on the mainland. You can also fly into Martha's Vineyard Airport, which is just a short drive from Oak Bluffs. If you're driving, you'll need to take a ferry to the island.
  • What outdoor activities can visitors enjoy in and around Oak Bluffs, MA?

    Oak Bluffs is a haven for outdoor enthusiasts! You can swim, sunbathe, or go kayaking at the beautiful beaches like Oak Bluffs Harbor, Joseph Sylvia State Beach, and East Beach. There's also great hiking and biking on the Island, with the Martha's Vineyard Trail offering stunning views.
  • When is the ideal time to plan a trip to Oak Bluffs, MA?

    The best time to visit Oak Bluffs depends on what you're looking for. If you want warm weather and lots of sunshine, July and August are ideal. If you prefer a more relaxed atmosphere and lower prices, spring and fall are great options.
  • What are the best walking or cycling routes in Oak Bluffs, MA?

    A walk or bike ride along the Oak Bluffs Harbor is a must-do. For a more challenging route, try the paved Martha's Vineyard Trail, which stretches for 15 miles across the island. You can also explore the charming streets of the historic district, taking in the gingerbread cottages and Victorian architecture.
  • What nearby towns or cities can be explored from Oak Bluffs, MA?

    Oak Bluffs is a great base for exploring the rest of Martha's Vineyard. You can easily visit Edgartown, a charming town with a historic harbour, or head to the busier town of Vineyard Haven for more shops and restaurants. If you're looking for stunning views, take a trip to Aquinnah, where you can see the Gay Head Cliffs.
  • What amenities can travelers expect from accommodations in Oak Bluffs, MA?

    You'll find a wide range of accommodation options in Oak Bluffs, from charming bed and breakfasts and cozy cottages to modern hotels and vacation rentals. Most accommodations offer amenities like Wi-Fi, parking, and laundry facilities. Many also have outdoor spaces like patios or balconies, perfect for enjoying the island's fresh air.

Popular destinations

Best Oak Bluffs, MA accommodations with a balcony

Charming, Cozy Spacious Home Within 1 Mile Walking Distance To Oak Bluffs - Oak Bluffs, MA
9.8 48 reviews

Charming, Cozy Spacious Home Within 1 Mile Walking Distance To Oak Bluffs

apartment, Oak Bluffs
This charming house is conveniently located just under 2 kilometres from Oak Bluffs Harbour and Inkwell Beach, offering easy access to the town’s attractions. It has consistently received excellent user ratings.
The property spans 158 square metres and comfortably accommodates up to 8 guests across its 5 bedrooms. It boasts a fully equipped kitchen, air conditioning, a private garden, a terrace, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Charming Vacation Home In Oak Bluffs. - Oak Bluffs, MA
No reviews

Charming Vacation Home In Oak Bluffs.

apartment, Oak Bluffs
This Oak Bluffs holiday home is situated within 3-5km of Farm Neck Golf Club, Oak Bluffs Public Library, and Circuit Avenue.
The four-bedroom property, sleeping eight, boasts a fully equipped kitchen, private balcony, free Wi-Fi, and pet-friendly accommodation, perfect for families or groups.
Newer Construction Edgartown Home With Ac, New  Furniture, On The Bike Path. - Oak Bluffs, MA
10 155 reviews

Newer Construction Edgartown Home With Ac, New Furniture, On The Bike Path.

apartment, Edgartown
This waterfront property in Edgartown is situated just 1.6km from Felix Neck Wildlife Sanctuary and Gus Ben David's World of Reptiles and Birds Park, offering a peaceful escape close to nature. The property has received excellent reviews from previous guests.
This 3-bedroom house has a floor area of 177 square metres and comfortably accommodates up to 6 guests. The property features a range of amenities, including a fully equipped kitchen, a Jacuzzi, a terrace, a garden, and parking, ensuring a comfortable and enjoyable stay.
Luxury Loft Historic Center Oak Bluffs - Oak Bluffs, MA
9.6 50 reviews

Luxury Loft Historic Center Oak Bluffs

apartment, Oak Bluffs
This Oak Bluffs holiday home is centrally located, within a short walk of Inkwell Beach and Oak Bluffs ferry terminal.
The 232 square metre (2500 square feet) property sleeps 13 guests in six bedrooms and three bathrooms, boasting a well-equipped kitchen, terrace, garden, spa, and tennis court access.

Best Oak Bluffs, MA accommodations with a kitchen

Cozy 3 Bedroom Apartment With King Bed On Main St. - Oak Bluffs, MA
9.9 97 reviews

Cozy 3 Bedroom Apartment With King Bed On Main St.

apartment, Oak Bluffs
This Oak Bluffs apartment is conveniently located just 0.5 km from the ferry, beaches, and public transport, making it easy to explore the island's attractions. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment has three bedrooms and can accommodate up to eight guests, making it ideal for families or groups of friends. The apartment features a fully equipped kitchen, air conditioning, a garden, and parking, along with a welcome package that includes beach towels, sunscreen, and other essentials.
Central Location For Your Vacation - Oak Bluffs, MA
9.6 307 reviews

Central Location For Your Vacation

apartment, Oak Bluffs
This raised ranch apartment, situated 8km from Oak Bluffs, offers easy access to Vineyard Haven (3km) and Edgartown (10km), providing a convenient base for exploring Martha's Vineyard.
The 93 square metre property features two bedrooms sleeping six, a fully equipped kitchen including a dishwasher, a garden, spa, and parking, plus high-speed internet and cable TV; Hulka Healing Therapies are also available.
Fresh Pond Chateau - Oak Bluffs, MA
8.0 1 review

Fresh Pond Chateau

house, Oak Bluffs
Fresh Pond Chateau is located in Hartsville, 8 kilometres from Edgartown Lighthouse and 5 kilometres from Martha's Vineyard Airport.
This 69 square metre cottage offers accommodation for up to 11 guests with two bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, a garden with a patio and outdoor fireplace, and on-site dining.
East Chop Cottage - Walk To Lighthouse & Beach! - Oak Bluffs, MA
9.8 149 reviews

East Chop Cottage - Walk To Lighthouse & Beach!

apartment, Oak Bluffs
This Oak Bluffs holiday home is situated in East Chop, a 0.8 km walk from East Chop Lighthouse, 1.9 km from Oak Bluffs harbour, and 1.6 km from the Oak Bluffs ferry, with a public beach 0.8 km away.
The self-catering property features a queen-size bed upstairs, a queen-size sleeper sofa downstairs, a basic kitchenette with refrigerator, toaster oven and kettle, plus a private driveway, outdoor shower, charcoal grill and covered porch seating six; it sleeps two guests.
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