Choose from 548 vacation rentals located in Oak Bluffs, Massachusetts. Top filters in Oak Bluffs include Internet / Wifi, Kitchen / Kitchenette, and TV. Prices range from $90 to $3,143 per night. Our most popular vacation rental types near Oak Bluffs are Condo and Hotel.

Top vacation rentals in Oak Bluffs

Deck off Living Room with Lagoon Pond view
5.0
Outstanding(98 Reviews)
House
 in Tisbury
Lagoon Pond House with Beach Access - Kayaker Paradise
6 guests · 2 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

Discover the beauty of Oak Bluffs with a stay at Lagoon Pond House with Beach Access - Kayaker Paradise, a top rated House with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

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Exterior
4.8
Outstanding(92 Reviews)
House
 in Oak Bluffs
Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!
7 guests · 4 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

Nestled in Oak Bluffs, this House is perfect for your next vacation. Enjoy Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!'s top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

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Welcome to the Cottage!!
4.8
Outstanding(124 Reviews)
Cottage
 in Oak Bluffs
Make Lasting Memories In This Adorable Vineyard Cottage!
4 guests · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Looking to create some memories in Oak Bluffs? Look no further than our Cottage, Make Lasting Memories In This Adorable Vineyard Cottage!. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

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Property view
4.1
Excellent(396 Reviews)
Condo
 in Oak Bluffs
Island Inn
Garden · Pool · Kitchen / Kitchenette

This Condo in Oak Bluffs, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

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Vacation rentals with internet & wifi in Oak Bluffs

Welcome to Blue Hollow
5.0
Outstanding(74 Reviews)
House
 in Vineyard Haven
Light-filled Contemporary Year-Round Pet-friendly Retreat
6 guests · 3 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette

House in Oak Bluffs, for $200 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

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Welcome to Pirate's Reef
5.0
Outstanding(67 Reviews)
House
 in Oak Bluffs
Modern, luxury 5-bed, 4.5-bath w\/full basement! Now booking for 2024!
12 guests · 5 bedrooms · 5 baths
Garden · Kitchen / Kitchenette · Air conditioner

Indulge in a peaceful retreat at Modern, luxury 5-bed, 4.5-bath w\/full basement! Now booking for 2024!, our elegant House in Oak Bluffs. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.

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Kitchen with stools for 4
5.0
Outstanding(75 Reviews)
House
 in Oak Bluffs
Multiple Ensuites, Central Air, Perfect Location
8 guests · 4 bedrooms · 4 baths
Garden · Kitchen / Kitchenette · Air conditioner

This House for $800 in Oak Bluffs, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Property view
4.3
Excellent(571 Reviews)
Hotel
 in Oak Bluffs
3star
Summercamp
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Indulge in a peaceful retreat at Summercamp, our elegant Hotel in Oak Bluffs. Enjoy amenities including Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.

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Oak Bluffs

Oak Bluffs travel guide

Let us help you plan your perfect Oak Bluffs vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Oak Bluffs, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Oak Bluffs?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • TV

What are the must-visit tourist attractions in Oak Bluffs, MA?

Oak Bluffs, MA is a popular tourist destination, with many attractions to explore. Here are the top four must-visit attractions:

  • The Flying Horses Carousel
  • The Martha's Vineyard Campmeeting Association Historic District
  • Oak Bluffs Harbor
  • The Tabernacle
Visitors to Oak Bluffs, MA should take the time to explore these amazing attractions and get a glimpse of the unique beauty and culture of the area.

How can I get around in Oak Bluffs, MA?

You can get around in Oak Bluffs, MA by:

  • Biking
  • Walking
  • Taking public transportation

Where can I find affordable accommodation in Oak Bluffs, MA?

Oak Bluffs, MA is a great destination for affordable accommodation options. Here are four great places to stay:

  • Seaside Inn: an affordable and cozy getaway from the hustle and bustle of everyday life.
  • Oceanview Properties: offering fully-furnished apartments at affordable prices.
  • The Summer House: a great value hotel with an outdoor pool and bar.
  • Cottage Court: a family-friendly motel with an outdoor pool and free Wi-Fi.

No matter what your budget or needs, Oak Bluffs, MA has something for everyone!

What is the culture like in Oak Bluffs, MA?

Oak Bluffs, MA is a small town located on Martha's Vineyard, and is known for its vibrant culture and community. Here are just a few of the things that make it so unique:

  • The town’s main attraction is its colorful, historic Victorian-style cottages.
  • The town is home to the annual Illumination Night, which is a celebration of lights around the harbor.
  • Every summer, Oak Bluffs hosts the Oak Bluffs Arts Festival, which is a celebration of the town’s art scene.
  • The town has a rich history of fishing, whaling, and farming, as well as a vibrant music scene.
  • The town is known for its delicious seafood, and has several restaurants and food vendors to choose from.

Is Oak Bluffs, MA safe to travel to?

Oak Bluffs, MA is safe to travel to. Here are a few safety tips to keep in mind:

  • Stay aware of your surroundings
  • Be mindful of any suspicious activity
  • Be aware of the local laws and regulations

By following these tips, you can enjoy a safe and pleasant trip to Oak Bluffs, MA.

What are the popular shopping destinations in Oak Bluffs, MA?

Oak Bluffs, MA is home to several popular shopping destinations. Here are a few of the most popular:

  • Oak Bluffs Town Hall: A great spot for local souvenirs and gifts.
  • Oak Bluffs Harbor: Find a variety of shops, restaurants, and galleries.
  • Oak Bluffs Public Library: A great place to purchase books, magazines, and other reading materials.

Where is Oak Bluffs, MA?

Oak Bluffs, MA is a town located on the island of Martha's Vineyard, off the coast of Massachusetts. It is known for its brightly colored Victorian cottages, beaches, and the Flying Horses Carousel, the oldest operating platform carousel in the United States.

What are the top things to do in Oak Bluffs, MA?

Oak Bluffs, MA is a charming seaside town located on the island of Martha's Vineyard. With its beautiful beaches, historic lighthouses, and unique attractions, there is plenty to do in Oak Bluffs. Here are some of the top things to do in Oak Bluffs:

  • Visit the Flying Horses Carousel
  • Explore the Inkwell Beach
  • Take a stroll along the Oak Bluffs Harbor
  • Check out the East Chop Lighthouse

What do I need to know before visiting Oak Bluffs, MA?

Before visiting Oak Bluffs, MA, it’s important to know that the town is known for its old-fashioned charm and vibrant, lively culture. Specifically, there are a few things that visitors should be aware of:

  • Oak Bluffs is a walking community, so it’s best to wear comfortable shoes and plan on doing a lot of walking.
  • Oak Bluffs is generally a safe area, but visitors should take precautions to keep themselves and their belongings safe.
  • There are plenty of restaurants, cafes, and shops to explore, and it’s best to budget extra time to explore all the town has to offer.

Visitors should also be prepared for the weather - it can get quite cool in the summer and very cold in the winter, so make sure to pack appropriately. With the right preparation, visitors can enjoy the beauty and charm of Oak Bluffs with ease!

What is the price range for rentals in Oak Bluffs?

Vacation rentals in Oak Bluffs have a price range between $90-$3,143. The average price for rentals in Oak Bluffs is $428 per night.

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