Find Historic Hotels in Oak Bluffs, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Oak Bluffs Historic Hotels

Tonight
Jan 26 - Jan 27
Tomorrow
Jan 27 - Jan 28
This weekend
Jan 30 - Feb 1
Next weekend
Feb 6 - Feb 8

Our top choices for Oak Bluffs historic hotels

Indoor pool

Inn on the Square

Inn on the Square
3.5 star property
Falmouth
8.6 out of 10, Excellent, (1,003 reviews)
"Familiar hotel "
United States
Wilfrido
The price is NT$3,551
NT$4,802 total
includes taxes & fees
Jan 27 - Jan 28
Inn on the Square
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.
View all properties

Top Oak Bluffs Hotel Reviews

Inn on the Square

Inn on the Square

10/10 Excellent
"Familiar hotel "
Wilfrido 4-night trip
Posted 8 days ago
Inn on the Square

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 walkable area.
How many historical hotels are located in Oak Bluffs?
In Oak Bluffs, there are 347 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 Cottage Museum and East Chop Light 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.

Explore a world of travel with Expedia