Best Oak Bluffs Vacation Rentals
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Best-rated
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Beach access
Capricorn House
- Heating
- Terrace
The 7-room Capricorn House Apartment Oak Bluffs includes a terrace and is located around a 25-minute walk from the historic East Chop Lighthouse. This apartment features Wi-Fi in the rooms.
Capricorn House
- Heating
- Terrace
Capricorn House
The 7-room Capricorn House Apartment Oak Bluffs includes a terrace and is located around a 25-minute walk from the historic East Chop Lighthouse. This apartment features Wi-Fi in the rooms.
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Beach access
Breezy Oak Bluffs Condo - Steps To Inkwell Beach!
- Cookware/ Kitchen utensils
- Free parking
- Ironing facilities
- Heating
- Sun loungers
The 2-bedroom Breezy Oak Bluffs Condo - Steps To Inkwell Beach! villa offers quick access to such tourist spots as the Oak Bluffs Town Beach, situated only a 6-minute walk away. The welcoming holiday home is suitable for 4 guests and provides bicycles for hire.
A variety of outdoor activities such as hiking can be enjoyed in the surroundings.
Breezy Oak Bluffs Condo - Steps To Inkwell Beach!
- Cookware/ Kitchen utensils
- Free parking
- Ironing facilities
- Heating
- Sun loungers
Breezy Oak Bluffs Condo - Steps To Inkwell Beach!
The 2-bedroom Breezy Oak Bluffs Condo - Steps To Inkwell Beach! villa offers quick access to such tourist spots as the Oak Bluffs Town Beach, situated only a 6-minute walk away. The welcoming holiday home is suitable for 4 guests and provides bicycles for hire.
A variety of outdoor activities such as hiking can be enjoyed in the surroundings.
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Beach access
Brewster House
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
- Garden area
Brewster House Villa Oak Bluffs is located merely an 11-minute walk from the Oak Bluffs Public Library and invites guests to join fishing.
Brewster House
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
- Garden area
Brewster House
Brewster House Villa Oak Bluffs is located merely an 11-minute walk from the Oak Bluffs Public Library and invites guests to join fishing.
Cheap Oak Bluffs Vacation Rentals
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Beach access
Garage Suite
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Garage Suite Oak Bluffs lies in a prime location in Oak Bluffs, nearly a 5-minute walk from the Long Point Wildlife Refuge. To elevate their stay, guests can make the most of fishing available on site.
Garage Suite
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Garage Suite
Garage Suite Oak Bluffs lies in a prime location in Oak Bluffs, nearly a 5-minute walk from the Long Point Wildlife Refuge. To elevate their stay, guests can make the most of fishing available on site.
Martha'S Vineyard Apt ~ 1 Mile To Inkwell Beach!
- Cookware/ Kitchen utensils
- Free parking
- Flat-screen TV
- Sun loungers
The spacious Martha'S Vineyard Apt ~ 1 Mile To Inkwell Beach! Oak Bluffs features a prime location a 20-minute walk from the Circuit Avenue and hosts up to 6 guests. This apartment offers parking on site and modern comforts like Wi-Fi.
A range of activities, such as hiking are offered in the area.
Martha'S Vineyard Apt ~ 1 Mile To Inkwell Beach!
- Cookware/ Kitchen utensils
- Free parking
- Flat-screen TV
- Sun loungers
Martha'S Vineyard Apt ~ 1 Mile To Inkwell Beach!
The spacious Martha'S Vineyard Apt ~ 1 Mile To Inkwell Beach! Oak Bluffs features a prime location a 20-minute walk from the Circuit Avenue and hosts up to 6 guests. This apartment offers parking on site and modern comforts like Wi-Fi.
A range of activities, such as hiking are offered in the area.
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Beach access
Bird'S Paradise
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
- Garden area
Bird'S Paradise Oak Bluffs villa entices guests to enjoy fishing and is located 3.5 km from such natural sites as the Scenic Inkwell Public Beach.
Bird'S Paradise
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
- Garden area
Bird'S Paradise
Bird'S Paradise Oak Bluffs villa entices guests to enjoy fishing and is located 3.5 km from such natural sites as the Scenic Inkwell Public Beach.
Pet Friendly Vacation Rentals Oak Bluffs Massachusetts
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Beach access
Victorian By The Sea
- Air conditioning
- Tea and coffee facilities
- Heating
- Garden area
- Patio
At Victorian By The Sea Villa Oak Bluffs, guests can enjoy fishing as well as a location just 9 minutes' walk from the Trinity Park Tabernacle.
Victorian By The Sea
- Air conditioning
- Tea and coffee facilities
- Heating
- Garden area
- Patio
Victorian By The Sea
At Victorian By The Sea Villa Oak Bluffs, guests can enjoy fishing as well as a location just 9 minutes' walk from the Trinity Park Tabernacle.
Yellow Brick Road House
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
Yellow Brick Road House Oak Bluffs villa is located nearly 25 minutes' walk from the Niantic Park, giving access to various tourist spots nearby. Guests can enjoy fishing at this Oak Bluffs holiday home, located just 1.9 km from the Flying Horses Carousel.
Yellow Brick Road House
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
Yellow Brick Road House
Yellow Brick Road House Oak Bluffs villa is located nearly 25 minutes' walk from the Niantic Park, giving access to various tourist spots nearby. Guests can enjoy fishing at this Oak Bluffs holiday home, located just 1.9 km from the Flying Horses Carousel.
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Beach access
Island Sanctuary
- BBQ facilities
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Heating
- Garden area
Island Sanctuary Villa Oak Bluffs is located about a 25-minute walk from the Trinity Park Tabernacle and provides fishing for active guests.
Island Sanctuary
- BBQ facilities
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Heating
- Garden area
Island Sanctuary
Island Sanctuary Villa Oak Bluffs is located about a 25-minute walk from the Trinity Park Tabernacle and provides fishing for active guests.
Oak Bluffs Vacation Rentals Oceanfront
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Beach access
Family Getaway
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
- Garden area
Situated 3.8 km from the Ocean Park, Family Getaway Villa Oak Bluffs entices guests to enjoy fishing in the area.
Family Getaway
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
- Garden area
Family Getaway
Situated 3.8 km from the Ocean Park, Family Getaway Villa Oak Bluffs entices guests to enjoy fishing in the area.
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Beach access
Sea Glen Cottage
- Ironing facilities
- Tea and coffee facilities
- Heating
- Garden area
- Patio
Sea Glen Cottage Oak Bluffs is located 4.8 km from the Cottage Museum and provides fishing for active guests.
Sea Glen Cottage
- Ironing facilities
- Tea and coffee facilities
- Heating
- Garden area
- Patio
Sea Glen Cottage
Sea Glen Cottage Oak Bluffs is located 4.8 km from the Cottage Museum and provides fishing for active guests.
Canary Cottage
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Patio
Situated 25 minutes' walk from the Eastville Point Beach, Canary Cottage Oak Bluffs invites guests to relax at a patio.
Canary Cottage
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Patio
Canary Cottage
Situated 25 minutes' walk from the Eastville Point Beach, Canary Cottage Oak Bluffs invites guests to relax at a patio.
Oak Bluffs Vacation Rentals with Private Pool
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Beach access
Oak Bluffs Cottage
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Patio
Situated just 6 minutes' walk from the Martha's Vineyard Camp Meeting Association, Oak Bluffs Cottage entices guests with fishing in the area.
Oak Bluffs Cottage
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Patio
Oak Bluffs Cottage
Situated just 6 minutes' walk from the Martha's Vineyard Camp Meeting Association, Oak Bluffs Cottage entices guests with fishing in the area.
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Top location
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Beach access
Winthrop Cottage
- Tea and coffee facilities
- Heating
- Patio
Winthrop Cottage Oak Bluffs enjoys a prime location only an 8-minute walk from the Cottage Museum, and invites guests to spend time on a patio. The holiday home features opportunities for fishing in the area, within a few blocks of the A Gallery Martha's Vineyard.
Winthrop Cottage
- Tea and coffee facilities
- Heating
- Patio
Winthrop Cottage
Winthrop Cottage Oak Bluffs enjoys a prime location only an 8-minute walk from the Cottage Museum, and invites guests to spend time on a patio. The holiday home features opportunities for fishing in the area, within a few blocks of the A Gallery Martha's Vineyard.
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Great deal
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Beach access
Sankofa Studio
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
To enjoy your vacation in Oak Bluffs, stay at Sankofa Studio Oak Bluffs, which is only 1.1 km from the Niantic Park and a mere 7 minutes on foot from the Art Gallery Artist Co-Op. Various sport options, such as fishing, are provided in the area.
Sankofa Studio
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
Sankofa Studio
To enjoy your vacation in Oak Bluffs, stay at Sankofa Studio Oak Bluffs, which is only 1.1 km from the Niantic Park and a mere 7 minutes on foot from the Art Gallery Artist Co-Op. Various sport options, such as fishing, are provided in the area.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Oak Bluffs, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Capricorn House |
8.9 / 10 (166 Reviews) |
From 325$ | |
| Breezy Oak Bluffs Condo - Steps To Inkwell Beach! |
10.0 / 10 (3 Reviews) |
From 571$ | |
| Brewster House |
9.0 / 10 (1 Reviews) |
From 224$ | |
| Garage Suite |
10.0 / 10 (1 Reviews) |
From 685$ | |
| Martha'S Vineyard Apt ~ 1 Mile To Inkwell Beach! |
8.7 / 10 (4 Reviews) |
From 828$ |
Frequently Asked Questions
Which Oak Bluffs vacation rentals are best for beach access?
Breezy Oak Bluffs Condo and Martha'S Vineyard Apt are both just steps away from Inkwell Beach. You can easily enjoy sunbathing, swimming, and beach activities without a long walk.
To skip crowds, plan your beach visits during weekdays before 10am.
Which Oak Bluffs vacation rentals have a view of the water?
Victorian By The Sea and Bird'S Paradise offer beautiful views of the ocean. You can enjoy stunning sunrises and sunsets right from your rental.
Book rooms on upper floors for the best views and stronger sea breezes.
What are the best vacation rentals in Oak Bluffs for large groups?
Family Getaway and Oak Bluffs Cottage provide spacious accommodations suitable for large parties. These rentals offer multiple bedrooms and communal areas for socializing.
Consider booking during the off-peak season, which runs from late September to early June, to find better rates on large rentals.
Which Oak Bluffs vacation rentals are best for families with kids?
Winthrop Cottage and Canary Cottage are both family-friendly with spacious layouts. They are equipped with kitchens and outdoor spaces for children to play.
Check for properties with playgrounds or family attractions nearby to keep kids entertained.
What vacation rentals in Oak Bluffs offer a hot tub or jacuzzi?
Bird'S Paradise and Vintage By The Sea feature hot tubs for relaxation. These amenities provide a perfect end to your busy beach days.
Book midweek stays to unlock lower prices for hot tub rentals.
Which Oak Bluffs vacation rentals are pet-friendly?
Capricorn House and Canary Cottage welcome pets. They offer ample space for your furry friends to roam.
Contact the property owner directly to confirm their specific pet policies and any associated fees.
What are the best luxury vacation rentals in Oak Bluffs?
Island Sanctuary and Bird'S Paradise are among the top luxury rentals, offering elegant interiors and stunning locations. They provide high-end amenities for an upscale stay.
Look for last-minute deals to find discounted rates on luxury rentals.
What are some unique local events in Oak Bluffs?
You can enjoy the Oak Bluffs Fireworks on the first Wednesday in August. It's a community celebration that's great for families and everyone can enjoy the show from various beaches.
Arrive early to grab a good spot on the beach, as crowds gather quickly.
How can I get around Oak Bluffs easily?
Biking is a popular and fun way to explore Oak Bluffs. Rentals are available around town, and many attractions are within cycling distance.
Consider renting a bike on weekdays to avoid the rental rush during weekends.
What local foods should I try during my visit?
The lobster rolls at Giordano's and the fried clam plate at The Seafood Shanty are must-tries. These local favorites highlight the fresh seafood available on the island.
Visit these restaurants early to avoid long wait times during peak lunch hours.