Oak Bluffs vacation rentals
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Top-rated vacation rentals in Oak Bluffs
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Cottage in Tisbury
4.96 out of 5 average rating, 209 reviewsNot Your Great Aunt's Island Cottage
CAR FERRY RESERVATIONS AVAILABLE - 7/7-7/13, 7/27-8/3, 8/24-31 In town, 1930's winterized cottage, lovingly updated by architect-owner. • Stylish informal decor, open floor plan, outdoor terrace • 2 blocks to Main Street/harbor/ferry/town beach/movie theater/playhouse • Central Air / Daikin Emura Zoned A/C • Close to bike rentals, restaurants, shops, spa, library, mini-golf, etc. • Large yard with wood/gas grills, bocce, corn hole, beach chairs, fire pit • Outdoor shower • 3BR + sleeping loft
Oct 20 – 27
Guest suite in Oak Bluffs
4.94 out of 5 average rating, 301 reviewsLovely 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!
Nov 16 – 23
Guest suite in Oak Bluffs
4.99 out of 5 average rating, 101 reviewsSea 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
Oct 21 – 28
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oak Bluffs vacation rentals
Oak Bluffs home rentals
Home in Oak Bluffs
4.94 out of 5 average rating, 116 reviewsThe Lighthouse
Mar 23 – 30
Home in Oak Bluffs
4.78 out of 5 average rating, 101 reviewsCozy Vacation Getaway On Bike Path
Sep 5 – 12
Home in Edgartown
4.96 out of 5 average rating, 181 reviewsBrand new gorgeous 2 bedroom guest house.
May 1 – 8
Home in Tisbury
4.98 out of 5 average rating, 244 reviewsVineyard Retreat: Just a mile from Tisbury center
Jun 1 – 8
Home in Edgartown
4.92 out of 5 average rating, 140 reviews✅Beach ✅Downtown ✅Restaurants/Bars ✅Bike Path
May 22 – 29
Home in West Tisbury
4.98 out of 5 average rating, 183 reviewsWest Tisbury Escape, Long Point Beach
Nov 11 – 18
Home in Edgartown
5.0 out of 5 average rating, 113 reviewsClose to Edgartown Village Center!
Oct 23 – 30
Home in West Tisbury
4.97 out of 5 average rating, 119 reviewsSecluded Up Island Cottage
Sep 16 – 23
Home in Edgartown
4.89 out of 5 average rating, 109 reviewsEdgartown Village: Walk to Everything
Dec 1 – 8
Home in Edgartown
4.86 out of 5 average rating, 138 reviewsMartha's Vineyard Vacation Home
Apr 14 – 21
Home in Aquinnah
4.98 out of 5 average rating, 124 reviewsMartha's Vineyard Oceanview Retreat
Apr 14 – 21
Home in Woods Hole
4.92 out of 5 average rating, 107 reviewsJuniper Point Cottage With Ocean View
Nov 2 – 9
Oak Bluffs cottage rentals
Cottage in Tisbury
4.98 out of 5 average rating, 309 reviewsMartha's Vineyard Getaway Cottage
Dec 9 – 16
Cottage in Mashpee
4.95 out of 5 average rating, 300 reviews★The Islander | Steps From Water, Fire Pit, AC★
Sep 5 – 12
Cottage in Sandwich
4.95 out of 5 average rating, 155 reviewsWaterfront Lake Cottage, Private Beach, Wow View!
Jan 9 – 16
Cottage in Fairhaven
4.79 out of 5 average rating, 277 reviewsOn the Beach Cottage in Fairhaven
Dec 11 – 18
Cottage in Falmouth
4.94 out of 5 average rating, 133 reviews“Cozy Cottage” on Great Bay
Dec 21 – 28
Cottage in Barnstable
4.99 out of 5 average rating, 120 reviewsBeach Glass Cottage - Pond Front
Nov 14 – 21
Cottage in Barnstable
4.89 out of 5 average rating, 119 reviewsOsterville Charming Cottage in the Heart of Wianno
Jun 25 – Jul 2
Cottage in Barnstable
4.91 out of 5 average rating, 140 reviewsCape Cottage - Walk to Beach, Ferries, and Town!
Mar 11 – 18
Cottage in Oak Bluffs
4.94 out of 5 average rating, 51 reviews55 Farm Pond Road, Oak Bluffs
Jun 1 – 8
Cottage in Tisbury
5.0 out of 5 average rating, 25 reviewsClassic Vineyard Cottage - Steps to Beach/Downtown
Apr 8 – 15
Cottage in Edgartown
5.0 out of 5 average rating, 54 reviewsStroll to Edgartown, AC, NEW Remodel, NEW Listing!
Dec 20 – 27
Cottage in Tisbury
4.97 out of 5 average rating, 33 reviewsWATERFRONT Cottage, Downtown w/ Beach
Apr 19 – 26
Oak Bluffs condo rentals
Condo in Oak Bluffs
4.95 out of 5 average rating, 21 reviewsLOCATION LOCATION!! Ocean- View TOP Floor Condo
Jun 16 – 23
Condo in Oak Bluffs
5.0 out of 5 average rating, 6 reviewsOcean View Gem, Walk to it All, No Car Needed!
Sep 12 – 19
Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsSunny 2bedroom condo w pool, walk to town
Nov 10 – 17
Condo in Mashpee
5.0 out of 5 average rating, 54 reviewsThe Cape Escape with Private Pool
Jun 5 – 12
Condo in Tisbury
4.98 out of 5 average rating, 44 reviewsShort Walk into Town - Nice Comfortable Reasonable
Nov 26 – Dec 3
Condo in Vineyard Haven
5.0 out of 5 average rating, 17 reviewsRelax....You're on Island Time......
Oct 19 – 26
Condo in Tisbury
4.76 out of 5 average rating, 17 reviewsLovely studio above garage
Jun 9 – 16
Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsPrivate 3bdrm Condo Tashmoo Woods
Jan 9 – 16
Condo in Mattapoisett
4.95 out of 5 average rating, 22 reviewsBrand new! Whole apartment, huge tub, full kitchen
Oct 19 – 26
Condo in Mashpee
4.97 out of 5 average rating, 99 reviewsSleep 6 @ New Seabury w/ Pool Access, All Seasons!
Jun 24 – Jul 1
Condo in Falmouth
4.97 out of 5 average rating, 34 reviewsLocation, location! Historic Downtown Falmouth!
Sep 30 – Oct 7
Condo in Barnstable
4.52 out of 5 average rating, 61 reviewsOceanside Cottage Apt across Craigville beach
Sep 27 – Oct 4
Quick stats about vacation 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 |
Frequently Asked Questions
What types of vacation rentals are available in Oak Bluffs?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Oak Bluffs. From over 30 condo rentals, over 410 house rentals to over 50 cottage rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Where should I stay in Oak Bluffs?
Make yourself at home in Oak Bluffs by choosing from our most frequently booked neighborhoods. We have over 630 vacation rentals in Eastville, over 630 vacation rentals in East Chop, and over 630 vacation rentals in West Chop.
Are there vacation rentals with a dedicated workspace in Oak Bluffs?
Yes! Work meets play with ease at over 320 vacation rentals in Oak Bluffs featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Oak Bluffs?
Four-legged friends are welcome in Oak Bluffs. Choose from more than 150 vacation rentals for guests traveling with pets.
How much does it cost to stay in cottage rentals in Oak Bluffs?
Experience the best of Oak Bluffs with our cottage rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Oak Bluffs have a bbq area?
Absolutely! We offer over 30 cottage rentals with a bbq area in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Oak Bluffs have self check-in?
Absolutely! We offer over 20 cottage rentals with self check-in in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Oak Bluffs have wifi?
Absolutely! We offer over 50 cottage rentals with wifi in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Are there Oak Bluffs house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Oak Bluffs, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Oak Bluffs have a gym?
Absolutely! We offer over 20 house rentals with a gym in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
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