Vacation rentals in Bend-in-the-Road Beach

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Top-rated vacation rentals in Bend-in-the-Road Beach

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Rental unit in Oak Bluffs

Sunny Private Apartment with Free Kayaking!

Studio apartment for 2 with a private entrance and private deck for you to relax on your island retreat. Full kitchen, beach chairs, beach bag/cooler and beach towels provided, along with free kayaking or paddle Boarding with Island Spirit Kayak! One mile from town and a 12 minute bike ride to the beach. This is the perfect location for access to Oak Bluffs restaurants, outdoor recreation and a peaceful neighborhood. Plus, you can join us in feeding the goats and chickens on the property!

$146 per night

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Home in Edgartown

Brand new gorgeous 2 bedroom guest house.

This is a gorgeous brand new 2 bedroom guest house on the bike path that leads to downtown Edgartown and both State Beach and South Beach, as well as 1/4 of a mile from the famous Morning Glory Farm Stand. There are cathedral ceilings in the living room, which provide a open, spacious feel. There is a large deck on the front of the house with a grill, table and chairs. Part of it is covered in shade. Separate parking for guests with privacy, as it sits 200+ feet from the main house.

$279 per night

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Cottage in Oak Bluffs

2022 brand new walk to everything Oak Bluffs!111I

This is a beautiful and brand new cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.

$262 per night