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Oak Bluffs Vacations

Pack those stellar shades. We have Oak Bluffs vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Oak Bluffs – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Oak Bluffs vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Oak Bluffs

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Oak Bluffs vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Oak Bluffs well.

Top Hotel Deals

See all 392 Hotels in Oak Bluffs
Summercamp

Summercamp

70 Lake Avenue, Oak Bluffs
4.0 out of 5.0

Situated in Oak Bluffs, this hotel is steps from Cottage Museum and Trinity Park Tabernacle. Flying Horses Carousel and Oak Bluffs Harbor are also within 5 ...

MV Surfside Hotel

MV Surfside Hotel

7 Oak Bluffs Avenue, Oak Bluffs
3.0 out of 5.0

Situated near the beach, this hotel is steps from Flying Horses Carousel, Oak Bluffs Harbor, and Information Booth. Oak Bluffs Town Beach and Ocean Park are ...

Martha's Vineyard Resort

Martha's Vineyard Resort

117 New York Ave, Oak Bluffs
3.5 out of 5.0

Situated in Oak Bluffs, this bed & breakfast is within a 15-minute walk of Oak Bluffs Public Library and Cottage Museum. Trinity Park Tabernacle and Flying Horses ...

Narragansett House

Narragansett House

46 Narragansett Av., Oak Bluffs
3.0 out of 5.0

Situated near the beach, this bed & breakfast is within a 5-minute walk of Ocean Park, Cottage Museum, and Trinity Park Tabernacle. Inkwell Beach and Flying ...

The Island Inn

The Island Inn

30 Island Inn Road, Oak Bluffs

Situated near the beach, this guesthouse is within 2 mi (3 km) of Inkwell Beach, Ocean Park, and Joseph Sylvia State Beach. Flying Horses Carousel and Trinity ...

Cape on Forest

Cape on Forest

66 Forest Avenue, Oak Bluffs
4.0 out of 5.0

Situated in Oak Bluffs, this vacation home is within 2 mi (3 km) of Farm Neck Golf Club, Oak Bluffs Public Library, and Trinity Park Tabernacle. Cottage Museum ...

The Walker House

The Walker House

27 Huntington, Oak Bluffs
4.0 out of 5.0

Situated in Oak Bluffs, this cottage is within a 10-minute walk of Oak Bluffs Public Library, Cottage Museum, and Trinity Park Tabernacle. Flying Horses Carousel ...

The Oak Bluffs Inn

The Oak Bluffs Inn

64 Circuit Ave, Oak Bluffs
3.5 out of 5.0

Located in Circuit Avenue, this bed & breakfast is steps from Trinity Park Tabernacle and Cottage Museum. Ocean Park and Flying Horses Carousel are also within ...

Sunset Meadows

Sunset Meadows

23 County Rd, Oak Bluffs
3.5 out of 5.0

Situated in Oak Bluffs, this vacation home is within 1 mi (2 km) of Oak Bluffs Public Library, Cottage Museum, and Trinity Park Tabernacle. Flying Horses Carousel ...

Pequot Hotel

Pequot Hotel

19 Pequot Avenue, Oak Bluffs
3.5 out of 5.0

Situated in the historical district, this hotel is within a 5-minute walk of Inkwell Beach and Ocean Park. Trinity Park Tabernacle and Cottage Museum are also ...

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.