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

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is S$197 per night from 27 Oct to 28 Oct
S$197
27 Oct - 28 Oct
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"People at the front desk were amazing. Very nice exceptional service."

Reviewed on 24 Sept, 2025

Summercamp
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue, Oak Bluffs, MA
The price is S$376 per night from 1 Oct to 2 Oct
S$376
1 Oct - 2 Oct
includes taxes & fees
8.8/10 Excellent! (823 reviews)
"I didnt like that there was no elevator. I am in my 60's. I was on the 3rd floor, no elevator. Loved everything else...I will return. Hopefully to an elevator."

Reviewed on 23 Aug, 2025

MV Surfside Hotel
Pequot Hotel

Pequot Hotel

3 out of 5
19 Pequot Avenue, Oak Bluffs, MA
The price is S$244 per night from 5 Oct to 6 Oct
S$244
5 Oct - 6 Oct
includes taxes & fees
9.2/10 Wonderful! (548 reviews)
"Easily walkable to all the shops. Superior staff"

Reviewed on 23 Sept, 2025

Pequot 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.

Popular places to visit

What to do in Oak Bluffs

* 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.