Deals on vacations and trips to Oak Bluffs

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Price found within the past 48 hours. Click for updated prices.
Hyannis Plaza Hotel

Hyannis Plaza Hotel

2.5 out of 5
Price was $668, price is now $583 per person
$583
per person
Dec 24 - Dec 27
found 20 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
Price was $2,049, price is now $1,667 per person
$1,667
per person
Dec 17 - Dec 23
found 18 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Vineyard Haven (MVY)
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.
Harbor View Hotel

Harbor View Hotel

5 out of 5
Price was $2,043, price is now $1,664 per person
$1,664
per person
Dec 17 - Dec 23
found 18 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
Price was $1,585, price is now $1,386 per person
$1,386
per person
Dec 17 - Dec 23
found 18 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Vineyard Haven (MVY)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and luggage storage are also on offer.
Courtyard Resort

Courtyard Resort

2 out of 5
Price was $1,265, price is now $1,119 per person
$1,119
per person
Dec 17 - Dec 23
found 18 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.

Top Oak Bluffs hotels deals

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
$179 nightly
The price is $200 total per night
$200 total
Oct 30 - Oct 31
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
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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
$184 nightly
The price is $205 total per night
$205 total
Oct 13 - Oct 14
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
$199 nightly
The price is $222 total per night
$222 total
Oct 5 - Oct 6
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
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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
Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

Oak Bluffs MA
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This vacation home includes a garden and barbecue grills.
Kitchen
Washer
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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 $583. 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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