Oak Bluffs Holiday Rentals from €200: Search Short-Term Rentals

Q: Can I find holiday rentals in Oak Bluffs?

Yes, there are holiday rentals in Oak Bluffs close to Flying Horses Carousel, or you can select a more secluded option if you're looking for a relaxing stay. The shops and waterfront are just a few reasons why tourists like Oak Bluffs. Allow lots of time to check out the beaches and wineries during your visit.

Q: What are some of the best holiday rentals that Oak Bluffs has to offer?

Victorian cottage overlooking downtown Oak Bluffs and the Harbor. : This highly rated holiday home rental in Oak Bluffs offers a fireplace, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Oak Bluffs are Quaint, ranch style home in Oak Bluffs with central air and Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs .

Q: How many holiday rentals will I find in Oak Bluffs?

Choose from 271 Expedia holiday rentals in Oak Bluffs for a memorable holiday.

Q: What can I see and do in Oak Bluffs?

Ocean Park and Oak Bluffs Town Beach are a couple of scenic spots to enjoy the outdoors, whereas Cottage Museum is one of the cultural attractions. Other places in town to visit include Circuit Avenue and Oak Bluffs Harbor.

Q: What are holiday rentals like in Oak Bluffs?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Bluffs. Holiday rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.

Check prices for these dates

In two weeks

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Our top choices for Oak Bluffs holiday rentals

A wooden deck with a white railing, two chairs, and a small table.

1. Make Lasting Memories In This Adorable Vineyard Cottage!

Oak Bluffs

Karen C.

includes taxes & fees

2 Sept - 3 Sept

A living room with a flat-screen TV on a stand, a black leather chair, and a sofa. There are two windows with curtains, one of which offers a view of the sea.

2. Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Oak Bluffs

Cassandra

includes taxes & fees

10 Sept - 11 Sept

A gravel driveway leading to a house surrounded by trees and a garden.

3. Lovely two bedroom apartment with indoor fireplace

Oak Bluffs

Aviva M.

includes taxes & fees

7 Sept - 8 Sept

An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

4. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Oak Bluffs

Katelyn K.

includes taxes & fees

1 Sept - 2 Sept

5. Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

Oak Bluffs

Rachael C.

includes taxes & fees

24 Sept - 25 Sept

A cozy living room with a wooden ceiling, a stone fireplace, a leather sofa, and a dining area with a table and chairs.

6. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

Oak Bluffs

"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...

Kate K.

includes taxes & fees

7 Sept - 8 Sept

A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

7. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Oak Bluffs

Sherri R.

includes taxes & fees

1 Oct - 2 Oct

A modern kitchen with white cabinets, a central island with blue drawers, and stainless steel appliances.

8. Brand New Guest house

Oak Bluffs

Elizabeth O.

includes taxes & fees

1 Oct - 2 Oct

A circular stone patio with Adirondack chairs and a small table in a forested area.

9. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Bethann N.

includes taxes & fees

1 Sept - 2 Sept

A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

Oak Bluffs

includes taxes & fees

1 Sept - 2 Sept

A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

16. Brand new! Lovely apartment-Vineyard Haven

Tisbury

Nancy K.

includes taxes & fees

7 Sept - 8 Sept

A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

17. The Club at New Seabury

New Seabury

Grayson

includes taxes & fees

7 Sept - 8 Sept

A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

18. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Tisbury

Adrienne W.

A modern living room with a sofa, chairs, a coffee table, and a dining area.

19. New Seabury Cape Condo + Pool & Beach Escape

New Seabury

Jeff V.

includes taxes & fees

7 Sept - 8 Sept

A wooden deck with wicker furniture, a table with a vase of flowers, and a view of a marina with boats.

20. WATERFRONT Downtown Cottage w/ Beach

Tisbury

John M.

includes taxes & fees

8 Sept - 9 Sept

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Top Oak Bluffs Hotel Reviews

Morgan Hotel

10/10 Excellent

"Room was spacious and clean. Convenient location to the beach and shops...all walkable. I will stay here again."

Faraway Martha's Vineyard

8/10 Good

"I enjoyed my stay in the Chappy House – Room 409, a suite with its on entrance from the outside. It was very well appointed and similar to a spacious one bedroom apartment without the kitchen. Must be capable of maneuvering stone pathways and steps to access it. Very nice for a long-term stay. I’d be interested in purchasing one! (Luxury vinyl plank flooring needs repairing in one hallway spot — barely noticeable.) 🙂"

Find out more about Oak Bluffs

Everything you need to know about Oak Bluffs holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Bluffs holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Bluffs holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oak Bluffs holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Bluffs. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Bluffs holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Bluffs holiday rentals we have selected for you start as low as €200 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oak Bluffs rentals

At Expedia, we put the best Oak Bluffs holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oak Bluffs rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Bluffs holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Bluffs. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find holiday rentals in Oak Bluffs?

Yes, there are holiday rentals in Oak Bluffs close to Flying Horses Carousel, or you can select a more secluded option if you're looking for a relaxing stay. The shops and waterfront are just a few reasons why tourists like Oak Bluffs. Allow lots of time to check out the beaches and wineries during your visit.

What are some of the best holiday rentals that Oak Bluffs has to offer?

Victorian cottage overlooking downtown Oak Bluffs and the Harbor.: This highly rated holiday home rental in Oak Bluffs offers a fireplace, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Oak Bluffs are Quaint, ranch style home in Oak Bluffs with central air and Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs.

How many holiday rentals will I find in Oak Bluffs?

Choose from 271 Expedia holiday rentals in Oak Bluffs for a memorable holiday.

What can I see and do in Oak Bluffs?

Ocean Park and Oak Bluffs Town Beach are a couple of scenic spots to enjoy the outdoors, whereas Cottage Museum is one of the cultural attractions. Other places in town to visit include Circuit Avenue and Oak Bluffs Harbor.

What are holiday rentals like in Oak Bluffs?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Bluffs. Holiday rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.

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Check prices for these dates

Our top choices for Oak Bluffs holiday rentals

1. Make Lasting Memories In This Adorable Vineyard Cottage!

2. Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

3. Lovely two bedroom apartment with indoor fireplace

4. Walk to Beach & Lighthouse: Oak Bluffs Studio!

5. Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

6. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs