Oak Bluffs Vacation Packages 2025/2026 from $1,343

Oak Bluffs flight + hotel vacation packages

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

Inn on Main

$1,343

per person

Nov 5 - Nov 9

found 6 hours ago

Roundtrip non-stop 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.

The Christopher, The Edgartown Collection

$1,766

per person

Oct 17 - Oct 19

found 1 day ago

Roundtrip flight included

Indianapolis (IND) 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.

The Sydney, The Edgartown Collection

$1,742

per person

Oct 17 - Oct 19

found 1 day ago

Roundtrip flight included

Indianapolis (IND) 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.

Summercamp

$1,523

per person

Oct 17 - Oct 19

found 1 day ago

Roundtrip flight included

Indianapolis (IND) to Vineyard Haven (MVY)

This hotel features free WiFi in public areas, concierge services, and self parking. A snack bar/deli and luggage storage are also provided.

Morgan Hotel

$1,549

per person

Oct 17 - Oct 19

found 1 day ago

Roundtrip flight included

Indianapolis (IND) to Vineyard Haven (MVY)

This hotel features free WiFi in public areas, luggage storage, and concierge services.

Top Oak Bluffs hotels deals

Summercamp

70 Lake Avenue, Oak Bluffs, MA

$236 nightly

$264 total

Oct 6 - Oct 7

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.

MV Surfside Hotel

7 Oak Bluffs Avenue, Oak Bluffs, MA

$380 nightly

$425 total

Sep 10 - Sep 11

Total with taxes and fees

This hotel features self parking and a garden. Luggage storage is also provided.

The Island Inn on Martha's Vineyard

30 Island Inn Rd, Oak Bluffs, MA

$350 nightly

$391 total

Oct 1 - Oct 2

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.

Pequot Hotel

19 Pequot Avenue, Oak Bluffs, MA

$169 nightly

$189 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.

Morgan Hotel

9 Healy Way, Oak Bluffs, MA

$296 nightly

$331 total

Sep 23 - Sep 24

Total with taxes and fees

This hotel features free WiFi in public areas, luggage storage, and concierge services.

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

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This vacation home features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.

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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

Sandy beaches, farmlands, fishing docks, harbor towns and tall lighthouses, Its Martha's Vineyard! It is around an hour of boat ride from Cape Cod to the Oak Bluffs. MV accessible only by boat or air.
This picture was of course taken in summer :) Bright sunny day with blue sky and lush green. In the background is the famous east chop lighthouse. The best of my memories of MV are from East Chop. We rented a bright Red scooter near the Oak Bluffs harbor after getting off from ferry, kicked off our slippers, rode to the sunset ;) I meant we drove to East Chop:)

Must Do : Get that pretty but awfully slow red scooter, drive to the light house, live the dream :)

East Chop Light

You can find out about the history of East Chop with a visit to East Chop Light. Stroll along the area's waterfront, or simply savor its wineries.

Inkwell Beach

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.

Oak Bluffs Town Beach

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 $1,343. 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.