Oak Bluffs Holidays

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Oak Bluffs Beach Holiday

There's nothing like an Oak Bluffs holiday 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 centre on your trip to Oak Bluffs, find a hotel around Inkwell Beach (0.64 kilometres away). If the plan is to hang around a while, consider securing one of our Oak Bluffs holiday 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 holiday 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 holiday in Oak Bluffs. Why not take a look at some private holiday 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 Harbour and Flying Horses Carousel are just some of the attractions that should be on your sightseeing list. With our Oak Bluffs holiday deals, you'll have more money in your back pocket to explore.

Top hotels in Oak Bluffs

Morgan Hotel

Morgan Hotel

2.5 out of 5
9 Healy Way Oak Bluffs MA
The price is S$238 per night from 16 Apr to 17 Apr
S$238
16 Apr - 17 Apr
includes taxes & fees
8.4/10 Very Good! (211 reviews)
We reserved a queen room and were upgraded to a king with a balcony. What a nice surprise! I called for help with the OpenKey app to open the front door. Friendly staff answered immediately and talked me through process while staying on the line. Stylish clean lobby. Simple white bedding with soft ...

Reviewed on 31 Mar, 2026

Morgan Hotel
The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
30 Island Inn Rd Oak Bluffs MA
8/10 Very Good! (32 reviews)
Clean room

Reviewed on 27 Dec, 2025

The Island Inn on Martha's Vineyard
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue Oak Bluffs MA
The price is S$251 per night from 27 Apr to 28 Apr
S$251
27 Apr - 28 Apr
includes taxes & fees
8.8/10 Excellent! (830 reviews)
Staff members, Alex and Amoy were wonderful. They were very accommodating and friendly.

Reviewed on 14 Oct, 2025

MV Surfside Hotel
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.

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What to do in Oak Bluffs

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.