Holiday rentals in Oak Bluffs

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Top-rated holiday rentals in Oak Bluffs

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 301 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

4–11 Feb

₹8,595 per night
Guest favourite

Guest suite in Oak Bluffs

4.99 out of 5 average rating, 101 reviews

Sea View Waterfront Beachfront Apartment

Prime location- right across the street from a sandy beach, a few minutes walk to the harbor, downtown, and transportation (boat, bus, etc). This beautiful street-level one-bedroom apartment sits across the street from the ocean, where you can take a dip and enjoy the beach. The apartment was recently redone and has a small bedroom with a queen size bed, small bathroom, full kitchen, and living room area with pull-out couch. Convenient to take the ferry into Oak Bluffs and walk to the apartment

21–28 Oct

₹33,538 per night
Superhost

Home in Oak Bluffs

4.82 out of 5 average rating, 179 reviews

Waterview, Private, Walk to Beach, Mile to Town

Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Please view our entire listing and reviews for more about our unique property.

18–25 Oct

₹38,081 per night

Popular amenities for Oak Bluffs holiday rentals

Stay near Oak Bluffs's top sights

Inkwell Beach31 locals recommend
Lookout Tavern52 locals recommend
Nancy's Restaurant42 locals recommend
The Black Dog Tavern52 locals recommend
The Barn32 locals recommend
Linda Jean's Restaurant48 locals recommend

Other great holiday rentals in Oak Bluffs

Guest favourite

Flat in Oak Bluffs

4.92 out of 5 average rating, 62 reviews

Downtown Oak Bluffs, 2nd floor Harbor house.

19–26 Feb

₹27,199 per night
Guest favourite

Home in Oak Bluffs

4.92 out of 5 average rating, 12 reviews

The Blue Lagoon, Oak Bluffs

11–18 Apr

₹44,907 per night
Guest favourite

Guest house in Oak Bluffs

5.0 out of 5 average rating, 48 reviews

Coastal Bungalow

23–30 May

₹38,765 per night
Guest favourite

Apartment in Oak Bluffs

5.0 out of 5 average rating, 20 reviews

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

26 May – 2 Jun

₹61,580 per night
Guest favourite

Home in Oak Bluffs

5.0 out of 5 average rating, 17 reviews

#CozyBluffs #Oak Bluffs | walk to town/ferry/beach

1–8 Jun

₹57,491 per night
Guest favourite

Home in Oak Bluffs

5.0 out of 5 average rating, 10 reviews

Airy and welcoming O.B apartment

23–30 Jul

₹55,062 per night
Guest favourite

Home in Oak Bluffs

5.0 out of 5 average rating, 45 reviews

New Pristine Luxury Home on Martha's Vineyard

11–18 Dec

₹67,110 per night
Guest favourite

Flat in Oak Bluffs

4.99 out of 5 average rating, 72 reviews

Martha's Vineyard Chic Getaway

26 Aug – 2 Sep

₹54,181 per night
Guest favourite

Home in Oak Bluffs

4.98 out of 5 average rating, 47 reviews

Oak Bluffs Cottage - Walk to Town & Beach

14–21 Oct

₹48,080 per night
Guest favourite

Guest house in Oak Bluffs

4.92 out of 5 average rating, 66 reviews

The Nest, Comfortable, Cozy and Convenient

5–12 Nov

₹36,760 per night
Guest favourite

Guest suite in West Tisbury

4.91 out of 5 average rating, 86 reviews

Studio Guest Suite in Modern Barn House

2–9 Apr

₹10,175 per night
Guest favourite

Home in Oak Bluffs

4.93 out of 5 average rating, 60 reviews

Martha's Vineyard Cottage

5–12 Sep

₹47,750 per night

Quick stats about holiday rentals in Oak Bluffs

Total rentals

680 properties

Rentals with a pool

80 properties have a pool

Pet-friendly rentals

150 properties allow pets

Family-friendly rentals

460 properties are a good fit for families

Total number of reviews

23T reviews

Nightly prices starting at

₹2,501 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Dukes County
  5. Oak Bluffs