Deals on vacations and trips to Oak Bluffs

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Price found within the past 48 hours. Click for updated prices.
The Villa Callo Inn

The Villa Callo Inn

3 out of 5
Price was $2,015, price is now $1,704 per person
$1,704
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Houston (HOU) to Hyannis (HYA)
This bed & breakfast features a terrace, barbecue grills, and free self parking. Enjoy the free local cuisine breakfast each morning. A garden and a picnic area are also provided.
Harbor View Hotel

Harbor View Hotel

5 out of 5
Price was $1,931, price is now $1,708 per person
$1,708
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip flight included
Houston (HOU) to Vineyard Haven (MVY)
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and free valet parking. Enjoy the seasonal outdoor pool and perks like free self parking.
The Christopher, The Edgartown Collection

The Christopher, The Edgartown Collection

3 out of 5
Price was $2,064, price is now $1,852 per person
$1,852
per person
Oct 22 - Oct 25
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
Free WiFi in public areas, a terrace, and a garden are available at this bed & breakfast. Enjoy the free self-serve breakfast each morning. A communal living room and express check-out are also provided.
Faraway Martha's Vineyard

Faraway Martha's Vineyard

4 out of 5
Price was $1,942, price is now $1,757 per person
$1,757
per person
Oct 22 - Oct 25
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
The Sydney, The Edgartown Collection

The Sydney, The Edgartown Collection

3.5 out of 5
Price was $1,905, price is now $1,733 per person
$1,733
per person
Oct 22 - Oct 25
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
This hotel features self parking and free WiFi in public areas. Enjoy the free self-serve breakfast each morning. Express check-out is also provided.

Top Oak Bluffs hotels deals

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
$212 nightly
The price is $237 total per night
$237 total
Oct 7 - Oct 8
Total with 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
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue Oak Bluffs MA
$239 nightly
The price is $267 total per night
$267 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel features self parking and a garden. Luggage storage is also provided.
Pet friendly
Air conditioning
Morgan Hotel

Morgan Hotel

2.5 out of 5
9 Healy Way Oak Bluffs MA
$288 nightly
The price is $322 total per night
$322 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel features free WiFi in public areas, luggage storage, and concierge services.
Free WiFi
Air conditioning
Pequot Hotel

Pequot Hotel

3 out of 5
19 Pequot Avenue Oak Bluffs MA
$169 nightly
The price is $189 total per night
$189 total
Oct 4 - Oct 5
Total with 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
The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
30 Island Inn Rd Oak Bluffs MA
Get rates
This resort's 3 outdoor tennis courts and seasonal outdoor pool are among the featured amenities. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free beach shuttle. A garden, a picnic area, and laundry facilities are also on offer.
Pool
Pet friendly
The Attleboro House

The Attleboro House

2.5 out of 5
42 Lake Ave Oak Bluffs MA
$205 nightly
The price is $229 total per night
$229 total
Oct 7 - Oct 8
Total with taxes and fees
Free WiFi in public areas is available at this hotel.
Free WiFi
Air conditioning
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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.

Stay near popular Oak Bluffs attractions

A beach with a lifeguard tower, a rocky breakwater, and the ocean.

Inkwell Beach

9.0/10 (154 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.
See properties

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 $1,704. 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

A row of colorful, historic houses with a central path.
A row of colorful Victorian-style houses with front porches and a well-maintained lawn.
A row of colorful Victorian-style houses with blue and yellow trim, a tree with white blossoms, and a paved street.
A rocky shoreline at sunset with a calm sea reflecting the colors of the sky.
A white lighthouse with a black top, surrounded by trees and a bench, overlooking a body of water.

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