Oak Bluffs vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Oak Bluffs vacation rentals

Stay near Oak Bluffs's top sights

Inkwell Beach31 locals recommend
Flying Horses Carousel82 locals recommend
ArtCliff Diner58 locals recommend
Lookout Tavern52 locals recommend
The Black Dog Tavern52 locals recommend
Linda Jean's Restaurant48 locals recommend

Quick stats about vacation rentals in Oak Bluffs

  • Total rentals

    760 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    26K reviews

  • Family-friendly rentals

    510 properties are a good fit for families

  • Pet-friendly rentals

    170 properties allow pets

  • Rentals with a pool

    80 properties have a pool

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 50 cottage rentals, over 460 house rentals to over 30 condo 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 710 vacation rentals in West Chop, over 710 vacation rentals in Eastville, and over 710 vacation rentals in East Chop.

  • Are there vacation rentals with a dedicated workspace in Oak Bluffs?

    Yes! Work meets play with ease at over 350 vacation rentals in Oak Bluffs featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Oak Bluffs?

    Experience the best of Oak Bluffs with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget 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 170 vacation rentals for guests traveling with pets.

  • Do house rentals in Oak Bluffs have a bbq area?

    Absolutely! We offer over 250 house rentals with a bbq area in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oak Bluffs have self check-in?

    Absolutely! We offer over 160 house rentals with self check-in in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oak Bluffs have wifi?

    Absolutely! We offer over 460 house rentals with wifi in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oak Bluffs have a gym?

    Absolutely! We offer over 30 house rentals with a gym 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 20 house rentals with pools in Oak Bluffs, available on Airbnb. Make a splash and soak up the sun in style!

Destinations to explore

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