Oak Bluffs Vacation Packages 2026 from $863

Oak Bluffs flight + hotel vacation packages

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

Margaritaville Resort Cape Cod

$863

per person

Sep 22 - Sep 26

found 18 hours ago

Roundtrip non-stop flight included

Detroit (DTW) 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. Enjoy the outdoor pool and perks like free self parking and free WiFi.

Chapter House

$897

per person

Aug 10 - Aug 14

found 1 hour ago

Roundtrip flight included

Detroit (DTW) to Hyannis (HYA)

A bar/lounge and a terrace are featured at this guesthouse, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.

Faraway Martha's Vineyard

$2,709

per person

Jul 30 - Aug 2

found 3 hours ago

Roundtrip non-stop flight included

New York (NYC) 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.

Vineyard Harbor Motel - Private Beach

$1,373

per person

Sep 25 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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.

Inn on Main

$1,270

per person

Aug 21 - Aug 24

found 6 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Top Oak Bluffs hotels deals

Summercamp

70 Lake Avenue Oak Bluffs MA

$506 nightly

$565 total

Jul 14 - Jul 15

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

7 Oak Bluffs Avenue Oak Bluffs MA

$246 nightly

$275 total

Jun 30 - Jul 1

Total with taxes and fees

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

$349 nightly

$390 total

Jun 30 - Jul 1

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

9 Healy Way Oak Bluffs MA

$385 nightly

$430 total

Jun 30 - Jul 1

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

$686 nightly

$766 total

Jun 30 - Jul 1

Total with taxes and fees

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

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

Oak Bluffs MA

Get rates

This vacation home features a water park, 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.

Popular places to visit

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

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.

A marina with boats docked along a sandy beach, surrounded by greenery and buildings.

Oak Bluffs Harbor

4.5/5(231 reviews)

Explore the waterfront in Oak Bluffs with a trip to Oak Bluffs Harbor. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

A beach with clear blue water, a sandy shore, and a few boats in the distance.

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.

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 $863. 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.