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Oak Bluffs Cottage Rentals & Holiday Homes
Find the best cottages in Oak Bluffs - We found 45 exact matches
- Oak Bluffs
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- East Chop
- 0.12 mi to center
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Breakfast
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Parking
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Ocean View
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Balcony/Terrace
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Breakfast
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Parking
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Ocean View
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Balcony/Terrace
- Massachusetts
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- Oak Bluffs
- 1.00 mi to center
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Balcony/Terrace
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View
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Air Conditioner
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Internet
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Balcony/Terrace
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View
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Air Conditioner
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Internet
- Massachusetts
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- Oak Bluffs
- 1.21 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
- Massachusetts
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- Oak Bluffs
- 1.07 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Massachusetts
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- Oak Bluffs
- 1.13 mi to center
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Balcony/Terrace
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View
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Air Conditioner
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Internet
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Balcony/Terrace
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View
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Air Conditioner
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Internet
- Massachusetts
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- Oak Bluffs
- 0.91 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
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- Oak Bluffs
- 1.00 mi to center
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Parking
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Internet
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Child Friendly
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Security/Safety
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Parking
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Internet
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Child Friendly
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Security/Safety
- Massachusetts
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- Oak Bluffs
- 0.89 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
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Kitchen
- Massachusetts
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- Oak Bluffs
- 1.21 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
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- Oak Bluffs
- 0.79 mi to center
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Parking
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Ocean View
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View
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Kitchen
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Parking
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Ocean View
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View
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Kitchen
- Oak Bluffs
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- East Chop
- 0.96 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
- Oak Bluffs
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- Lagoon Heights
- 1.21 mi to center
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Hot Tub
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Parking
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Kitchen
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Air Conditioner
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Hot Tub
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Parking
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Kitchen
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Air Conditioner
- Oak Bluffs
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- Lagoon Heights
- 0.95 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Oak Bluffs
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- East Chop
- 0.16 mi to center
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Oceanfront
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Hot Tub
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Parking
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Ocean View
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Oceanfront
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Hot Tub
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Parking
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Ocean View
- Massachusetts
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- Oak Bluffs
- 0.46 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Massachusetts
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- Oak Bluffs
- 1.24 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
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- Oak Bluffs
- 0.85 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Oak Bluffs
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- Lagoon Heights
- 0.47 mi to center
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Kitchen
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Air Conditioner
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Internet
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Child Friendly
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Kitchen
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Air Conditioner
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Internet
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Child Friendly
- Oak Bluffs
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- Circuit Avenue
- 0.02 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
- Massachusetts
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- Oak Bluffs
- 0.88 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
- Massachusetts
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- Oak Bluffs
- 1.12 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
- Oak Bluffs
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- Lagoon Heights
- 0.86 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Massachusetts
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- Oak Bluffs
- 1.27 mi to center
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Oceanfront
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Ocean View
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Balcony/Terrace
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View
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Oceanfront
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
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- Oak Bluffs
- 0.88 mi to center
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Ocean View
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Balcony/Terrace
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View
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Kitchen
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Ocean View
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Balcony/Terrace
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View
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Kitchen
About Oak Bluffs Cottage Rentals on Peter Bay Villas
Searching for cottages to rent near Oak Bluffs? Peter Bay Villas features more than 45 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Oak Bluffs have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Peter Bay Villas’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Oak Bluffs.
Are you planning to travel to the lakeside, beach, or mountain area? Peter Bay Villas’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Peter Bay Villas boasts of 45 holiday cottages and places to stay in Oak Bluffs. The site provides unique Airbnb, VRBO, Peter Bay Villas-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Oak Bluffs Cottage Rentals
What are the top rated Cottage Rentals in Oak Bluffs?
There are a lot of options in Oak Bluffs. If you plan on staying in the Oak Bluffs area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Oak Bluffs:
- Arrowsmith Cottage - Oak Bluffs Near Eastville Beach; Steps to bike path.
- Well-loved, classic OB Cottage w/updated essentials and an unbeatable location.
- 6 Beds! Walk to Beach, Ferry, Ocean Park and OB!
- Quiet Getaway Within Walking Distance Of All Oak Bluffs Has To Offer.
- Cottage w/ distant WATERVIEW, 0.2 miles off Circuit Ave, quiet & private
- Sunny Oak Bluffs cottage minutes from beach
- Delilah & Joseph Pierce House
- 1-Bedroom cottage, 200ft from the beach
- This Charming OB Cottage has Everything in Great location
- Waterfront Family Escape with Dock & Private Beach in Oak Bluffs
How much does it cost to rent a cottage in Oak Bluffs?
The average cost for a cottage rental in Oak Bluffs is $852 per night. Peterbayvillas has a wide list of great cottages near Oak Bluffs that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Oak Bluffs that allow pets?
Yes, here are the top cottage rentals in Oak Bluffs that allow you to bring your pet:
- Beautiful Carriage House on the Chop
- Oak Bluffs Cottage
- The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs
- 4 bedroom cottage in Oak Bluffs Martha's Vineyard
See all pet-friendly vacation rentals in Oak Bluffs on Peterbayvillas
Do you have any rental cottages in Oak Bluffs that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Oak Bluffs to find one that works for you.
Are there quality cottages in Oak Bluffs that have indoor swimming pools?
As of 2026, the data from Peterbayvillas shows that there are Over 45 private swimming pools or cottages with indoor pools in the Oak Bluffs area along with other great amenities.