
Oak Bluffs Vacations
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Find the Best Oak Bluffs Vacation Packages
Oak Bluffs Beach Vacation
There's nothing like an Oak Bluffs vacation to put a bounce in your step. The soothing melody of rolling surf and the smell of fresh ocean air will help refresh your mind and body. To be close to the town center on your trip to Oak Bluffs, find a hotel around Inkwell Beach (0.64 kilometers away). If the plan is to hang around a while, consider securing one of our Oak Bluffs vacation packages. Not only will you save some money, you'll also have other stunning beaches around you to explore, like Joseph Sylvia State Beach and Eastville Point Beach. We call that a win-win!
Things You Should Know About Oak Bluffs
- Spend your vacation by the water and let the hassles of daily life drift away with the ocean breeze. Book one of our Oak Bluffs beach hotels and enjoy a little beachside bliss.
- No matter your budget or style, you'll find an ideal place to stay for your vacation in Oak Bluffs. Why not take a look at some private vacation homes, like The Attleboro House and Marthas Vineyard Resort? They're popular with visitors of all sorts.
- Some 3,800 people live in Oak Bluffs. If you'd like advice about what to see and do in this area, why not start a conversation with one or two of the locals? Our Oak Bluffs things to do page is also a handy source of information.
- Inkwell Beach, Oak Bluffs Harbor and Flying Horses Carousel are just some of the attractions that should be on your sightseeing list. With our Oak Bluffs vacation deals, you'll have more money in your back pocket to explore.
Oak Bluffs Hotel Deals

Summercamp
70 Lake Avenue, Oak Bluffs, MA
The price is ¥68,024 per night from Sep 4 to Sep 5
¥68,024
¥75,983 total
Sep 4 - Sep 5
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Staff is amazing which makes this place my number one hotel in Martha’s Vineyard. Clean and modern atmosphere. Will return again."
Reviewed on Jul 29, 2025

The Island Inn on Martha's Vineyard
30 Island Inn Rd, Oak Bluffs, MA
The price is ¥34,505 per night from Sep 3 to Sep 4
¥34,505
¥69,644 total
Sep 3 - Sep 4
includes taxes & fees
8/10 Very Good! (7 reviews)
"Staff, cleanliness and the property"
Reviewed on Aug 2, 2025

Pequot Hotel
19 Pequot Avenue, Oak Bluffs, MA
The price is ¥48,495 per night from Sep 1 to Sep 2
¥48,495
¥54,168 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (532 reviews)
"Would recommend this hotel to friends and family. Plan on returning in the future."
Reviewed on Jul 29, 2025
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.
What to do in Oak Bluffs

Massachusetts Highlights: Freedom Trail, Salem & More Tour
¥7,383
per adult

Massachusetts: Smartphone-Based Audio Tour Bundle
¥7,383
per traveler

New Budget Friendly Shared 4 hour African American Heritage Tour
¥19,200
per adult
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.