Oak Bluffs vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

1 of 3 pages
1 of 3 pages

Popular amenities for Oak Bluffs vacation 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

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

$30 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.

Destinations to explore

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