Oak Bluffs cottage rentals

We found 138 cottage rentals — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any cottage rentals in Oak Bluffs?
Pick one of our 138 cottage rentals and start making plans for your Oak Bluffs trip. Whether you want to stay in Lagoon Heights, East Chop, West Chop or another well-known neighbourhood, these cosy and charming cottages offer more room to move compared to a hotel.
How much does it cost to stay in a cottage rental in Oak Bluffs?
Check out our cottage rental listings in Oak Bluffs for an idea of prices. If you're wanting to save, try using our "Discounts" filter. It'll show you any cottages offering special promotions, whether that's a monthly, weekly or new listing discount.
When is the best time to rent a cottage in Oak Bluffs?
Follow the crowds and book your cottage rental in May. With the average temperatures ranging between 11ºC and 14ºC, this is when most people head to Oak Bluffs. For a more relaxed vibe, it's worth looking at the low season. Whenever you decide to visit this part of Martha's Vineyard, a Stayz cottage will guarantee your holiday is an unforgettable experience.
Where can I rent an Oak Bluffs holiday cottage with great views?
When searching for your cottage rental in Oak Bluffs, use the "Location" filter. This will help you choose the types of areas you prefer to stay in, whether that's near nature or somewhere close to the action.
Does Oak Bluffs have any lakeside cottages?
Get up to beautiful views every morning and lull yourself to sleep with the soothing sounds of nature at night in one of Stayz's lakeside cottage rentals. Throw in some outdoor adventures during the daytime and you've got yourself a superb holiday by the water. To find out if there are any lakeside cottages in Oak Bluffs, use our "Location" filter and then select "Lake."
What are the top things to do in Oak Bluffs?
Arrange a few excursions from your cottage rental, making sure you stop by Old Silver Beach, Inkwell Beach and Falmouth Heights Beach. These leading Oak Bluffs attractions are family friendly, so the whole crew can have a great time together.
Why should I book my holiday cottage with Stayz?
Stayz provides customer support from booking until the end of your trip, so every aspect of your holiday is hassle-free. Plus we think our cottage rentals are pretty special — think amenity-packed stays ideal for families and charming options that set the stage for a romantic break. Book with us and you can also make use of flexible cancellation policies and benefits like deposit and payment protection.