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
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!
19–26 Jan
€ 127 per night
4.94 out of 5 average rating, 300 reviews
Guest favourite
Guest suite in Oak Bluffs
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
17–24 JanIndividual Host,
€ 434 per night
4.99 out of 5 average rating, 101 reviews
Superhost
Home in Oak Bluffs
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 OctIndividual Host,
€ 512 per night
4.82 out of 5 average rating, 179 reviews

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
Guest house in Oak Bluffs
Coastal Bungalow
31 Aug – 7 Sep
€ 569 per night
5.0 out of 5 average rating, 48 reviews
Guest favourite
Guest house in Oak Bluffs
Oak bluffs cottage Perfect place to honeymoon!
12–19 AprIndividual Host,
€ 293 per night
4.98 out of 5 average rating, 64 reviews
Guest favourite
Apartment in Oak Bluffs
LOCATION LOCATION!! Ocean- View TOP Floor Condo
15–22 SepIndividual Host,
€ 826 per night
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Oak Bluffs
Airy and welcoming O.B apartment
28 Aug – 4 Sep
€ 757 per night
5.0 out of 5 average rating, 10 reviews
Guest favourite
Guest house in Oak Bluffs
The Nest, Comfortable, Cozy and Convenient
9–16 DecIndividual Host,
€ 458 per night
4.92 out of 5 average rating, 66 reviews
Guest favourite
Flat in Oak Bluffs
Martha's Vineyard Chic Getaway
26 Aug – 2 SepProfessional Host,
€ 704 per night
4.99 out of 5 average rating, 72 reviews
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
12–19 Jun
€ 855 per night
5.0 out of 5 average rating, 45 reviews
Guest favourite
Home in Oak Bluffs
Vineyard Stroll
24–31 OctIndividual Host,
€ 697 per night
4.93 out of 5 average rating, 70 reviews
Guest favourite
Home in Oak Bluffs
#CozyBluffs #Oak Bluffs | walk to town/ferry/beach
8–15 FebIndividual Host,
€ 517 per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Oak Bluffs
NEW Modern Open Floor Plan House in Heart of OB
4–11 MayIndividual Host,
€ 1,103 per night
5.0 out of 5 average rating, 19 reviews
Guest favourite
Guest house in Oak Bluffs
Mermaid Cottage
29 Dec – 5 JanIndividual Host,
€ 427 per night
4.99 out of 5 average rating, 73 reviews
Guest favourite
Home in Oak Bluffs
Oak Bluffs Cottage - Walk to Town & Beach
6–13 DecIndividual Host,
€ 636 per night
4.98 out of 5 average rating, 47 reviews

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

23K reviews

Nightly prices starting at

€ 28 before taxes and fees

Destinations to explore

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