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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

Charming Vineyard Haven Retreat W/ Heated Pool, Walk To Town, & Tashmoo Beach! - Oak Bluffs, MA
No reviews

Charming Vineyard Haven Retreat W/ Heated Pool, Walk To Town, & Tashmoo Beach!

apartment, Tisbury
This Vineyard Haven retreat is located in Tisbury, offering convenient access to Vineyard Haven town and beaches, with Inkwell Beach and Cape Cod Beaches nearby, and is a short distance from the Woods Hole Ferry Terminal.
This four-bedroom, two-bathroom apartment accommodates up to eight guests and features a private vineyard, a heated swimming pool, air conditioning, and a kitchen equipped with a microwave oven and dishwasher, with parking available.
The Island Inn On Martha's Vineyard - Oak Bluffs, MA
8.4 53 reviews

The Island Inn On Martha's Vineyard

resort, Oak Bluffs
The Island Inn on Martha's Vineyard, a resort in Oak Bluffs, is located less than 2 kilometres from Joseph Sylvia State Beach, Inkwell Beach, and Seaview Beach, with Oceanographic Park and Circuit Avenue also within 3 kilometres.
This establishment offers a seasonal swimming pool, outdoor tennis courts, barbecue grills, complimentary Wi-Fi in common areas, and free on-site parking, with a complimentary shuttle service to the beach.
Luxury! Heated Pool & Spa!tennis! Firepit! Hammock - Oak Bluffs, MA
9.4 33 reviews

Luxury! Heated Pool & Spa!tennis! Firepit! Hammock

house, Oak Bluffs
This family-friendly holiday home is located in Oak Bluffs, just a short distance from the beach, Circuit Avenue, and other local attractions. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The spacious 4-bedroom property spans 223 square metres and features a range of amenities including a private pool, a Jacuzzi, a tennis court, and a barbecue grill. Guests can enjoy the beautiful weather in the private garden or relax in the comfortable living spaces.
Relax & Unwind: Poolside Marthas Vineyard Stay - Oak Bluffs, MA
8.8 3 reviews

Relax & Unwind: Poolside Marthas Vineyard Stay

apartment, Oak Bluffs
This spacious 272 m² holiday home in Oak Bluffs offers convenient access, being just an 11-minute drive from the Martha's Vineyard Preservation Trust Historic Buildings.
The family-friendly property accommodates up to 10 guests with 5 bedrooms and 5 bathrooms, featuring a private swimming pool, terrace with a fire pit, and a well-equipped kitchen with a dishwasher and microwave, alongside Wi-Fi and air conditioning.

Best family friendly Oak Bluffs, MA lodging

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

Charming, Cozy Spacious Home Within 1 Mile Walking Distance To Oak Bluffs - Oak Bluffs, MA
9.8 49 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.
Oak Bluffs Family Retreat - Private Roundabout, Walk To The Beach & Downtown Ob. - Oak Bluffs, MA
10 26 reviews

Oak Bluffs Family Retreat - Private Roundabout, Walk To The Beach & Downtown Ob.

apartment, Oak Bluffs
This charming house is located in Oak Bluffs, a short 1.6km walk from Martha's Vineyard Hospital and less than 1.6km from Oak Bluffs Public Library and Oak Bluffs Harbour. This accommodation has received excellent reviews from previous guests, highlighting its comfortable and convenient features.
This three-bedroom, three-bathroom house offers 186 square metres of space, comfortably accommodating up to six guests. The house features a fully equipped kitchen, laundry facilities, air conditioning, a barbecue grill, and a comfortable living space with a TV and a sofa bed.
Brand New Guest House - Oak Bluffs, MA
10 7 reviews

Brand New Guest House

apartment, Oak Bluffs
This Oak Bluffs apartment is conveniently located near Circuit Avenue and Main Street, offering easy access to attractions such as the Cottage Museum and Martha's Vineyard Museum.
The two-bedroom, two-bathroom property sleeps five guests and includes in-unit laundry facilities, WiFi, air conditioning, and a fully equipped kitchen with a fridge, microwave, and dishwasher; nearby activities include the Flying Horses Carousel and Oak Bluffs Fishing Pier.
Quintessential Mv Home Near Oak Bluffs, Beach & Harbor - Oak Bluffs, MA
9.6 59 reviews

Quintessential Mv Home Near Oak Bluffs, Beach & Harbor

apartment, Oak Bluffs
This charming Victorian house is located on a peaceful lane in East Chop, just a short walk or drive from Oak Bluffs' beach, harbour, and town centre. The property has received excellent ratings for location, cleanliness, and overall experience.
The spacious home spans 232 square metres and comfortably sleeps nine guests across four bedrooms and four bathrooms. Amenities include a fully equipped kitchen, air conditioning, a private garden, a terrace with a barbecue, and a basement with an arcade machine, ensuring a comfortable and enjoyable stay for families or groups.

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

Serene Private Home W/ Large Deck & Yard On Conservation Land - Oak Bluffs, MA
No reviews

Serene Private Home W/ Large Deck & Yard On Conservation Land

apartment, Oak Bluffs
This Oak Bluffs residence is situated on a private acre in a quiet cul-de-sac, offering a serene retreat yet conveniently located a 1.6 to 2.4 kilometre drive from beautiful beaches and within walking distance to a bus stop and local parks.
This spacious 201 square metre holiday home accommodates up to 12 guests with 4 bedrooms and 3 bathrooms, featuring a large deck, a fully equipped kitchen with a dishwasher and microwave, central air conditioning, and a dog-friendly policy, all set within 4,048 square metres of land adjacent to conservation woods.
4 Mi To Inkwell Beach: Home In Oak Bluffs! - Oak Bluffs, MA
No reviews

4 Mi To Inkwell Beach: Home In Oak Bluffs!

house, Oak Bluffs
This Oak Bluffs holiday home is situated 6.4 km from Inkwell Beach and 3 km from Martha's Vineyard Airport, offering convenient access to key attractions.
The 158 square metre property boasts three bedrooms, two bathrooms, and sleeps thirteen guests, featuring a fully equipped kitchen with dishwasher, air conditioning, a private garden, on-site parking, and free Wi-Fi.
Sunny Side Up - Oak Bluffs, MA
No reviews

Sunny Side Up

house, Oak Bluffs
Sunny Side Up, a four-bedroom house in Oak Bluffs, is situated 1.8-2.6 km from Eastville, Inkwell, and Oak Bluffs Town beaches and 11.7 km from Edgartown Lighthouse.
This self-catering property sleeps eight, boasting three bathrooms, a well-equipped kitchen with dishwasher, patio, garden, and parking, plus cable TV and a fireplace; its proximity to Martha's Vineyard Airport (7 km) adds to its convenience.
Breezy Oak Bluffs Condo - Steps To Inkwell Beach! - Oak Bluffs, MA
9.9 60 reviews

Breezy Oak Bluffs Condo - Steps To Inkwell Beach!

house, Oak Bluffs
This Oak Bluffs apartment is located a short walk from Inkwell Beach and Oak Bluffs Town Beach, approximately 2.4km from Joseph Sylvia State Beach, and 9.4km from Edgartown Lighthouse.
The 102 square metre property features two bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, in-unit laundry, a private balcony with sea views, and free Wi-Fi; it comfortably accommodates families or groups.

Best Oak Bluffs, MA accommodations with a kitchen

Cozy Downtown Studio - Walk To Ferry & Town - Oak Bluffs, MA
9.5 4 reviews

Cozy Downtown Studio - Walk To Ferry & Town

apartment, Oak Bluffs
This downtown Oak Bluffs studio flat is located a short walk from the ferry and the shops and restaurants of Circuit Avenue, offering glimpses of Oak Bluffs Harbour and Nantucket Sound.
This compact 34-square-metre studio apartment accommodates up to four guests, featuring a galley kitchen with a fridge and dishwasher, one bathroom with an extra-large shower, and air conditioning.
Beach Home Just 0.8 Miles To Farm Neck Golf Club! - Oak Bluffs, MA
9.6 139 reviews

Beach Home Just 0.8 Miles To Farm Neck Golf Club!

apartment, Oak Bluffs
This charming holiday home is situated in a peaceful neighbourhood in Oak Bluffs, just 1.6 kilometres from the pond and less than 1.6 kilometres from Farm Neck Golf Course, offering a tranquil retreat whilst being close to the island's attractions. The property has received excellent ratings for its cleanliness, location and user experience, making it a popular choice for families and groups.
The spacious home comprises three bedrooms and two bathrooms, comfortably accommodating up to six guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, a large deck, a fire pit, and a shared outdoor space, perfect for relaxing and enjoying the beautiful surroundings.
Bright 2-bedroom Apt Near Walking & Biking Trails - Oak Bluffs, MA
10 46 reviews

Bright 2-bedroom Apt Near Walking & Biking Trails

apartment, Oak Bluffs
This Oak Bluffs apartment is conveniently located on Martha's Vineyard, approximately 16km from Edgartown, Vineyard Haven, and Oak Bluffs itself, offering easy access to public transport, walking trails, the YMCA, and tennis courts.
The self-catering flat comprises two bedrooms, one bathroom, and sleeps four, featuring a full kitchen with dishwasher, air conditioning, a private yard with outdoor seating, and access to an outdoor shower; upcoming upgrades include new furniture and a larger kitchen table.
East Chop Cottage - Oak Bluffs, MA
10 2 reviews

East Chop Cottage

house, Oak Bluffs
This Martha's Vineyard cottage is located in a quiet district, 500 metres from the beach and 1.2 kilometres from Oak Bluffs.
This accommodation sleeps up to four guests and features a private patio, an outdoor shower, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher, all within a 5-minute walk of the beach and a 15-minute walk to Oak Bluffs.
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