Deals on vacations and trips to Oak Bluffs

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Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Vineyard Haven (MVY)
This motel features a private beach and luggage storage. Take advantage of the free self parking.
The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 21
found 5 hours ago
Roundtrip flight included
Washington (DCA) to Vineyard Haven (MVY)
Luggage storage is available at this hotel. Take advantage of the free self parking.
Inn on Main

Inn on Main

3.5 out of 5
Save 100% on your flight
per person
Aug 7 - Aug 12
found 3 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Hyannis (HYA)
This bed & breakfast doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A garden, a snack bar/deli, and a library are also on offer.
Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Save 100% on your flight
per person
Aug 7 - Aug 12
found 3 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Hyannis (HYA)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a snack bar/deli are also on offer.
Morgan Hotel

Morgan Hotel

2.5 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 21
found 5 hours ago
Roundtrip flight included
Washington (DCA) to Vineyard Haven (MVY)
This hotel features free WiFi in public areas, luggage storage, and concierge services.

Top Oak Bluffs hotels deals

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
$310 nightly
The price is $346 total per night
$346 total
Jun 8 - Jun 9
Total includes taxes and fees
This hotel features free WiFi in public areas, concierge services, and self parking. A snack bar/deli and luggage storage are also provided.
Free WiFi
Air conditioning
Pequot Hotel

Pequot Hotel

3 out of 5
19 Pequot Avenue, Oak Bluffs, MA
$269 nightly
The price is $300 total per night
$300 total
Jun 8 - Jun 9
Total includes taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A business center, a terrace, and a garden are also on offer.
Breakfast included
Parking included
Morgan Hotel

Morgan Hotel

2.5 out of 5
9 Healy Way, Oak Bluffs, MA
$274 nightly
The price is $306 total per night
$306 total
Jun 9 - Jun 10
Total includes taxes and fees
This hotel features free WiFi in public areas, luggage storage, and concierge services.
Free WiFi
Air conditioning
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
The Attleboro House

The Attleboro House

2.5 out of 5
42 Lake Ave, Oak Bluffs, MA
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Free WiFi in public areas is available at this hotel.
Free WiFi
Air conditioning
The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2 out of 5
30 Island Inn Rd, Oak Bluffs, MA
$403 nightly
The price is $450 total per night
$450 total
Jun 22 - Jun 23
Total includes taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this resort. WiFi in public areas is free. A garden, a picnic area, and barbecue grills are also on offer.
Pool
Pet friendly
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Sandy beaches, farmlands, fishing docks, harbor towns and tall lighthouses, Its Martha's Vineyard! It is around an hour of boat ride from Cape Cod to the Oak Bluffs. MV accessible only by boat or air. This picture was of course taken in summer :) Bright sunny day with blue sky and lush green. In the background is the famous east chop lighthouse. The best of my memories of MV are from East Chop. We rented a bright Red scooter near the Oak Bluffs harbor after getting off from ferry, kicked off our slippers, rode to the sunset ;) I meant we drove to East Chop:) Must Do : Get that pretty but awfully slow red scooter, drive to the light house, live the dream :)

East Chop Light

You can find out about the history of East Chop with a visit to East Chop Light. Stroll along the area's seaside, or simply savor its wineries.

East Chop Light

Inkwell Beach

4.5/5(31 reviews)

If a restful vacation is part of your travel plans, Inkwell Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along this relaxing area's waterfront, or simply enjoy its wineries.

Inkwell Beach

Oak Bluffs Town Beach

4.5/5(10 reviews)

If a restful vacation is part of your travel plans, Oak Bluffs Town Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along the waterfront or visit the shops in this relaxing area.

Oak Bluffs Town Beach

Frequently asked questions

How much are vacation packages to Oak Bluffs?
Treat yourself to an unforgettable experience in Oak Bluffs with a vacation package starting at just $838. Organizing your flights, tours and hotels with Travelocity is so simple. And even better, our great deals will leave you with extra cash for fun, fun, fun!
How long should my Oak Bluffs vacation be?
Most travelers choose to spend around 3 nights in Oak Bluffs, but how long you stay is your call. If you intend to check out all the exciting things this destination has to offer, why not hang around for a couple of extra nights?
Where can I get the best vacation package deals for Oak Bluffs?
You can grab amazing Oak Bluffs package deals with Travelocity. Choose from 400 partner airlines and 1,000,000 worldwide properties and turn those travel fantasies into reality.
Why should I book my Oak Bluffs vacation bundle with Travelocity?
You’ll not only enjoy great savings, but you can also access our 24/7 customer support, quality service and a Price Match Guarantee. Wander across the globe, discover hidden gems and create unforgettable memories — we’ll take care of the little details.
Will I save money on my Oak Bluffs car rental if I combine it with my hotel or flight?
With an Oak Bluffs vacation package, you can combine your car, flight and hotel bookings and save some serious money. If you’re in the mood to see the best of this wonderful region, why not make tracks to Fenway Park? This must-see attraction is 70 mi from Oak Bluffs. With your own wheels, you’ll be there in a jiffy.
Which airport is best for Oak Bluffs?
T.F. Green Airport (PVD) (50 mi away from downtown), Martha’s Vineyard Airport (MVY) (5 mi away from central Oak Bluffs) and Nantucket Memorial Airport (ACK) (30 mi away from central Oak Bluffs) are the main hubs in Oak Bluffs.
What is there to do in Oak Bluffs?
While hopping off the tourist trail can be rewarding, you really shouldn’t miss the big sights that make a place famous. Inkwell Beach and Oak Bluffs Harbor are a couple of them in Oak Bluffs.
Where should I stay when visiting Oak Bluffs?
Many people opt to spend their nights at the MV Surfside Hotel. It’s a great base for your Oak Bluffs escape.

Photos of local treasures

Browse Oak Bluffs vacation photos for more inspiration

Oak Bluffs
Oak Bluffs
Oak Bluffs
Photo by Fun Travelog
Photo by Fun Travelog
Photo by Amritha
Photo by Amritha