Find Historic Hotels in Oak Bluffs, MA

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Check availability on Oak Bluffs Historic Hotels

Tonight
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Oak Bluffs Historic Hotels

Fridge, microwave, oven, stovetop
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

Barnstable
10.0 out of 10, Exceptional, (30)
"House is beautiful and well equipped, and located in a lovely quiet neighborhood. Host was quickly responsive to all of our inquiries. Overall a great spot for a family vacation. "
United States
Sheila B.
The price is SAR 1,876
SAR 3,655 total
includes taxes & fees
4 Jan - 5 January 2026
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Terrace/patio
The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard

Katama
9.8 out of 10, Exceptional, (24)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is SAR 845
SAR 2,038 total
includes taxes & fees
8 Dec - 9 Dec
The Seashell Cove - Martha's Vineyard
Courtyard
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 star property
Vineyard Haven
9.0 out of 10, Wonderful, (608)
"Love the stay, w I’ll definitely stay again!"
United States
Jerrick
The price is SAR 494
SAR 551 total
includes taxes & fees
18 Dec - 19 Dec
Vineyard Harbor Motel - Private Beach
Beach nearby
The Palmer House Inn

The Palmer House Inn

3.5 star property
Falmouth
9.6 out of 10, Exceptional, (175)
"Nice place to stay"
United States
Brian
The price is SAR 716
SAR 820 total
includes taxes & fees
31 Dec - 1 January 2026
The Palmer House Inn
Exterior
Inn on the Square

Inn on the Square

3.5 star property
Falmouth
8.6 out of 10, Excellent, (1017)
"Great location Comfortable beds Reasonably price "
United States
Thomas
The price is SAR 406
SAR 552 total
includes taxes & fees
18 Dec - 19 Dec
Inn on the Square
Exterior
Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!

Onset
9.6 out of 10, Exceptional, (22)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is SAR 639
SAR 1,577 total
includes taxes & fees
5 Dec - 6 Dec
Spacious and Bright , Very Close to Beach!
Exterior
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Onset
9.8 out of 10, Exceptional, (28)
"The space was perfect for our needs. The beds were comfortable, the rooms were very clean. If needed, we would definitely come back to this rental."
United States
Lynn
The price is SAR 639
SAR 1,577 total
includes taxes & fees
7 Dec - 8 Dec
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
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
"The room was very clean and it was wonderful to have a restaurant onsite. It was only open for breakfast and lunch, but I had an excellent omlette. The staff at the Inn were professional and polite. I definitely would stay there again. The location is extremely convenient. Short walk to shops and restaurants."
Barbara 2-night trip
Posted 1 day ago
Inn on the Square

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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 348 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 Ocean Park, Oak Bluffs Town Beach, and Inkwell Beach. 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.