Deals on vacations and trips to Oak Bluffs

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Price found within the past 48 hours. Click for updated prices.
Hyannis Travel Inn

Hyannis Travel Inn

2.5 out of 5
Price was $390, price is now $329 per person
$329
per person
Nov 7 - Nov 10
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Hyannis (HYA)
This hotel features an outdoor pool and an indoor pool. Enjoy the hot tub and free perks like continental breakfast and free self parking. Free WiFi in public areas, a terrace, and express check-out are also on offer.
Hyannis Plaza Hotel

Hyannis Plaza Hotel

2.5 out of 5
Price was $650, price is now $486 per person
$486
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hyannis (HYA)
An outdoor pool is featured at this hotel, along with free self parking. There's a garden and multilingual staff can provide around-the-clock assistance.
The Villa Callo Inn

The Villa Callo Inn

3 out of 5
Save 100% on your flight
Price was $1,195, price is now $956 per person
$956
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Courtyard Resort

Courtyard Resort

2 out of 5
Price was $551, price is now $453 per person
$453
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hyannis (HYA)
This hotel features an indoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a garden, and a picnic area are also offered.
Inn on Main

Inn on Main

3.5 out of 5
Price was $899, price is now $765 per person
$765
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hyannis (HYA)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free cooked-to-order breakfast each morning. A garden, a snack bar/deli, and a library are also on offer.

Top Oak Bluffs hotels deals

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
$241 nightly
The price is $269 total per night
$269 total
Sep 30 - Oct 1
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
$234 nightly
The price is $261 total per night
$261 total
Sep 3 - Sep 4
Total with taxes and fees
This hotel features self parking and a garden. Luggage storage is also provided.
Pet friendly
Air conditioning
Pequot Hotel

Pequot Hotel

3 out of 5
19 Pequot Avenue Oak Bluffs MA
$186 nightly
The price is $208 total per night
$208 total
Sep 27 - Sep 28
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
Morgan Hotel

Morgan Hotel

2.5 out of 5
9 Healy Way Oak Bluffs MA
$281 nightly
The price is $313 total per night
$313 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel features free WiFi in public areas, luggage storage, and concierge services.
Free WiFi
Air conditioning
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
Get rates
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.
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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 $329. 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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