A row of colorful, historic houses with a central path.

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Our top choices for Oak Bluffs historic hotels

A cozy living room with a fireplace, bookshelves, a dining area, and a staircase.

1. Madison Inn

Madison Inn
2.5 star property
Oak Bluffs
9.8 out of 10, Exceptional, (84 reviews)
"Good location, friendly staff. More breakfast/drink options would have been good."
United States
Melissa
The price is NT$6,802
NT$7,785 total
includes taxes & fees
Nov 22 - Nov 23
Madison Inn
A modern living room with a sofa, armchairs, and a coffee table. A neon sign with the name "MORGAN" is visible on the wall.

2. Morgan Hotel

Morgan Hotel
2.5 star property
Oak Bluffs
8.6 out of 10, Excellent, (277 reviews)
"Location was Perfect!"
United States
Anika
The price is NT$4,847
NT$5,548 total
includes taxes & fees
Nov 16 - Nov 17
Morgan 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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Top Oak Bluffs Hotel Reviews

The Coonamessett

The Coonamessett

10/10 Excellent
"The Coonamessett is a beautiful inn overlooking the water. The suite I stayed in was absolutely stunning. Breakfast is excellent with some vegan options such as mixed fruit and oat milk. The inn is extremely comfortable, clean, and well-maintained. My suite even had two walk-in closets."
Janet 3-night trip
Posted 2 days ago
The Coonamessett

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 373 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 Flying Horses Carousel.
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.

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