Find Historic Hotels in South Orleans, MA

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Our top choices for South Orleans historic hotels

Indoor pool
Courtyard Resort

Courtyard Resort

Courtyard Resort
2.0 star property
Hyannis
8.2 out of 10, Very Good, (45)
"Clean and inexpensive"
United States
Robert
$109 nightly
The price is $125
Jan 4 - Jan 5, 2026
Total with taxes and fees
Courtyard Resort
Free daily continental breakfast
Comfort Inn Hyannis - Cape Cod

Comfort Inn Hyannis - Cape Cod

Comfort Inn Hyannis - Cape Cod
2.5 star property
Hyannis
8.0 out of 10, Very Good, (1000)
"Nice hotel had a perfect stay"
United States
David
$98 nightly
The price is $112
Dec 24 - Dec 25
Total with taxes and fees
Comfort Inn Hyannis - Cape Cod
Pelham 1 King + Balcony + Sleeper | Premium bedding, iron/ironing board, free WiFi, bed sheets
Pelham on Main

Pelham on Main

Pelham on Main
2.5 star property
West Dennis
8.6 out of 10, Excellent, (401)
"Would definitely stay again! Staff is welcoming, area is quiet and convenient. Renovated rooms are also a plus. 10/10."
United States
Nate
$193 nightly
The price is $221
Dec 18 - Dec 19
Total with taxes and fees
Pelham on Main
TV, fireplace, books
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (101)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
$365 nightly
The price is $418
Dec 18 - Dec 19
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Interior
Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach

Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach

Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach
Dennis
9.6 out of 10, Exceptional, (177)
"Fenced in yard was perfect and close walk to both beach and restaurants."
United States
Mike Kayla B.
$306 nightly
The price is $350
Dec 26 - Dec 27
Total with taxes and fees
Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach
Outdoor dining
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (50)
"House was perfect for our family reunion! "
United States
Gregg H.
$465 nightly
The price is $533
Dec 18 - Dec 19
Total with taxes and fees
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
TV, books
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
Chatham
8.6 out of 10, Excellent, (26)
"This was a very nice place to stay, the location was perfect. A short walk to town and centrally located on the Cape as a whole. This home had all of the amenities need for a comfortable stay."
United States
Jeffrey A.
$473 nightly
The price is $541
Dec 18 - Dec 19
Total with taxes and fees
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
Beach nearby, sun loungers, beach towels
Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location

Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location

Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location
Dennis
10.0 out of 10, Exceptional, (32)
"The place was adorable and the location was perfect. We could walk to the beach, to an amazing little bakery and it gave us great access to our weekend of wedding events.Irene had suggested sunset at Mayflower Beach and it was spectacular. We will be back in the future."
United States
Natalie D.
$643 nightly
The price is $736
Jan 1 - Jan 2, 2026
Total with taxes and fees
Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location
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 South Orleans Hotel Reviews

Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"yes"
david 2-night trip
Posted 2 days ago
Bayside Resort Hotel

Frequently asked questions

What should a history enthusiast expect from a trip to South Orleans?
A trip to the historical places in South Orleans is likely at the top of your sightseeing list. You can also explore all there is to see and do such as the seafood restaurants and beaches
How many historical hotels will I find in South Orleans?
South Orleans is home to 45 hotel accommodations bookable on Expedia though you won't find many designated historic hotels.
What are the must-see historical places and other sights in South Orleans?
A favorite place to visit is Cape Cod Beaches. You'll also find Nickerson State Park and Orleans Bowling Center in the area.
What is a historic hotel like in South Orleans?
By choosing a historic hotel, you can sleep in a place that has an official historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be considered a historic hotel as long as it's of special interest. Traditional architecture and period features can be admired in the guestrooms or communal spaces of historic hotels in South Orleans, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, while "historic hotel" is a term often used in the U.S. though overall the terms are quite similar. The building and architecture of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value as well as how it influenced the community.
Do historic hotels in South Orleans have modern facilities?
Yes, every effort is made to preserve historic facades and treasured traditions, while interiors have safety features and modern conveniences. Visitors can expect the usual amenities from a contemporary hotel such as Smart TVs, WiFi, and updated bathroom facilities. When you book a historic hotel in South Orleans, it doesn't mean you're picking a place that's rundown or uncomfortable for guests.

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