Oak Bluffs Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
9.2/10 Wonderful! (1,003 reviews)
Amazing staff and I love the complementary coffee experience
Reviewed on Nov 3, 2025
MV Surfside Hotel
7 Oak Bluffs Avenue, Oak Bluffs, MA
8.8/10 Excellent! (830 reviews)
The location was convenient and the property was exactly what we needed - clean, basic, accommodations. Two minor issues - the room reeked of bleach when we arrived and we had to open the windows to air it out. Second, the frint desk hours aren’t posted and it was hard to reach someone to check in ...
Reviewed on Oct 12, 2025
Morgan Hotel
9 Healy Way, Oak Bluffs, MA
8.4/10 Very Good! (193 reviews)
Great little hotel. All communication is done via texting. There is no one on site at this hotel. However it’s a great little hotel near restaurants and bars.
Reviewed on Nov 3, 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 Self-Guided Audio Tour Bundle: 10+ Tours
￥7,631
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
￥7,631
per traveler
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
