Find Historic Hotels in Oak Bluffs, MA

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Pick from 2 Oak Bluffs Historic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Madison Inn
2.5 star property
9.6 out of 10, Exceptional, (76)
"Great location! Very clean rooms and friendly staff."
Madison Inn
Pequot Hotel
3.0 star property
9.4 out of 10, Exceptional, (453)
"Pequot Hotel was clean and great location (a block away from beach, several blocks from main street with restaurants and shops). The room we stayed (Middle Queen Room) was so tiny. It just enough to put the queen bed in. No fridge or microwave."
The price is AED 988
AED 1,104 total
includes taxes & fees
12 Jun - 13 Jun
Pequot Hotel
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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.

Frequently asked questions

What can a history enthusiast expect from a trip to Oak Bluffs?
You’re likely already making plans to see the historical sites while you’re staying in Oak Bluffs. Visit the shops and waterfront while you’re in town. You can also take some time enjoying the beaches in this relaxing area.
How many historical hotels are located in Oak Bluffs?
In Oak Bluffs, there are 398 hotel accommodations bookable on Expedia but not many designated as historic hotels.
What are the most important historical places and other sights to visit in Oak Bluffs?
Landmarks like East Chop Light and Cottage Museum in Oak Bluffs might be worth a visit. Natural beauty is on display at Oak Bluffs Town Beach, Inkwell Beach, and Ocean Park. A couple of additional sights to add to your agenda are Circuit Avenue and Oak Bluffs Harbor.
What is a historic hotel like in Oak Bluffs?
Guests who book a historic hotel can stay in a place that has an officially recognized historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be identified as a historic hotel provided that it’s of special interest. Traditional architecture and period features are often found in the guestrooms or communal spaces of historic hotels in Oak Bluffs, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
“Heritage hotel” is a term often used in Asia and Europe, while “historic hotel” is a term often used in the U.S. but overall the terms are quite similar. The physical building and architecture of a historic hotel is generally the most important aspect. For a heritage hotel, often it’s the cultural value and how it shaped the community.
Do historic hotels in Oak Bluffs have modern facilities?
Hotels include modern conveniences and safety features you might expect, while every effort is made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities, and the popular amenities found in most hotels will be available in a historic hotel. Rest assured that when you select a historic hotel in Oak Bluffs, you won’t be staying at a place that is rundown or uncomfortable.

Recent reviews of Oak Bluffs hotels
Expedia verified reviews