Oak Bluffs Vacation Packages 2026 from $1,349

Oak Bluffs flight + hotel vacation packages

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

The Villa Callo Inn

$1,349

per person

Dec 26 - Dec 31

found 1 day ago

Roundtrip flight included

New Orleans (MSY) 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.

Vineyard Harbor Motel - Private Beach

$1,561

per person

Dec 24 - Dec 30

found 4 hours ago

Roundtrip flight included

Columbus (CMH) 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.

Anchor In Distinctive Waterfront Lodging

$1,398

per person

Dec 24 - Dec 30

found 4 hours ago

Roundtrip flight included

Columbus (CMH) to Hyannis (HYA)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a snack bar/deli are also on offer.

Margaritaville Resort Cape Cod

$1,969

per person

Dec 24 - Dec 30

found 4 hours ago

Roundtrip flight included

Columbus (CMH) to Hyannis (HYA)

This smoke-free resort features a full-service spa, a water park, and 2 restaurants. There's fun for all ages with a lazy river and a children's pool, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas.

Harbor View Hotel

$1,925

per person

Dec 24 - Dec 30

found 4 hours ago

Roundtrip flight included

Columbus (CMH) to Vineyard Haven (MVY)

This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour 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.

Top Oak Bluffs hotels deals

Summercamp

70 Lake Avenue Oak Bluffs MA

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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

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

Pequot Hotel

19 Pequot Avenue Oak Bluffs MA

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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

9 Healy Way Oak Bluffs MA

$149 nightly

$171 total

Nov 8 - Nov 9

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

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

Quaint, ranch style home in Oak Bluffs with central air

Oak Bluffs MA

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A garden is available at this vacation home.

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 $1,349. 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.