Title: Book the Best HISTORIC Hotels in Madison in 2026 | Expedia.ca [Madison Travel Guide](https://expedia.ca/Madison.dx8791)[Hotels in Madison](https://expedia.ca/Madison-Hotels.d8791.Travel-Guide-Hotels)[Vacation Rentals in Madison](https://expedia.ca/Madison-Vacation-Rentals.d8791.Travel-Guide-VacationRentals)[Flights to Madison](https://expedia.ca/Cheap-Flights-To-Madison.d8791.Travel-Guide-Flights)[Madison Car Rentals](https://expedia.ca/Car-Rentals-In-Madison.d8791.Car-Rental-Guide)[Madison Vacation Packages](https://expedia.ca/Madison.d8791.Destination-Travel-Guides) ![A Connecticut home in autumn surrounded by colorful foliage.](https://images.trvl-media.com/place/8791/579db867-4a05-43b0-acaa-e0e5981d4123.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Madison, CT from CA $252 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Madison Historic Hotels Tonight [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-12-17&endDate=2025-12-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Madison historic hotels ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/e52f4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/825be1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/433807ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/6b6b7167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood Cottage @ Saybrook Point Marina, 2 King Beds [](https://www.expedia.ca/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information) Old Saybrook Center 9.6/10 Exceptional (39) "Great property, would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) charles b. [](https://www.expedia.ca/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information) ![Breakfast and brunch served](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/b7b5473a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/d634e2d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/0d578d42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/d9b0e3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omni New Haven Hotel at Yale [](https://www.expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) Downtown New Haven 8.6/10 Excellent (1007) "Great traditional New Haven Hotel. From check in to check out staff was very professional and welcoming. Great job for all of your staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $233 CA $268 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943221/f03e38bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943221/de85c2ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943221/6c2db181.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943221/81d5d1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport NY - King Suite 1 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-NY-King-Suite-1.h71943221.Hotel-Information) Greenport 10/10 Exceptional (5) "Perfect Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dean J. CA $246 CA $383 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-NY-King-Suite-1.h71943221.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/ace6fff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/5a4689b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/d4937d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/d820b069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Studio| Near Yale| Downtown New Haven [](https://www.expedia.ca/New-Haven-Hotels-Charming-Studio-Near-Yale-Downtown-New-Haven.h107557460.Hotel-Information) Downtown New Haven 8.8/10 Excellent (11) "Convenient location. Just off Rte 91\. Easy street parking. The studio is as pictured - exposed brick walls, high ceilings. Everything you need for a short stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lois G. CA $95 CA $252 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/New-Haven-Hotels-Charming-Studio-Near-Yale-Downtown-New-Haven.h107557460.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943243/3e210a29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943243/d6619038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943243/265999f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943243/da3cce8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech - Deluxe King 5 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Deluxe-King-5.h71943243.Hotel-Information) Greenport 8.6/10 Excellent (4) "I thoroughly enjoyed my stay. I was upgraded before arriving at the hotel and was very pleased with my stay. The staff were kind and accommodating, I will definitely return." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ayana M. CA $274 CA $418 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Deluxe-King-5.h71943243.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/91000000/90870000/90868400/90868316/d014d1a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/91000000/90870000/90868400/90868316/d1a711aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90870000/90868400/90868316/7669a961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/91000000/90870000/90868400/90868316/4a7e96de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### #25 \*Massive\* 5 BR in Downtown Southington\* [](https://www.expedia.ca/Southington-Hotels-25-Massive-5-BR-In-Downtown-Southington.h90868316.Hotel-Information) Southington 8.8/10 Excellent (3) "The property was perfect for my family and I. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marguerite CA $219 CA $550 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Southington-Hotels-25-Massive-5-BR-In-Downtown-Southington.h90868316.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/78e2058f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/e21d51ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/6f63cb0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/52c91315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech - King Suite 2 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-King-Suite.h71943229.Hotel-Information) Greenport 10/10 Exceptional (2) "Excellent one night stay." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Patrick M. CA $246 CA $383 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-King-Suite.h71943229.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0884fbbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/ca1c5177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Petite King Room 7 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) Greenport 9.0/10 Wonderful (4) "We thoroughly enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Parent From The Heart, Inc. E. CA $219 CA $347 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96780000/96774900/96774831/w1024h766x0y1-96bbf316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96780000/96774900/96774831/5536d3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/97000000/96780000/96774900/96774831/w1023h768x0y0-61973062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96780000/96774900/96774831/7f41124c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Loft apartment in the heart of downtown New Haven and blocks from the Omni Hotel [](https://www.expedia.ca/New-Haven-Hotels-Loft-Apartment-In-The-Heart-Of-Downtown-New-Haven-And-Blocks-From-The-Omni-Hotel.h96774831.Hotel-Information) Downtown New Haven CA $143 CA $255 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/New-Haven-Hotels-Loft-Apartment-In-The-Heart-Of-Downtown-New-Haven-And-Blocks-From-The-Omni-Hotel.h96774831.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943253/3f78fdb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943253/ec0d1670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943253/4f3be2fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943253/bfa72810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Two-Bedroom Apartment 8 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Two-Bedroom-Apartment-8.h71943253.Hotel-Information) Greenport CA $398 CA $580 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Two-Bedroom-Apartment-8.h71943253.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2025-12-31&endDate=2026-01-01®ionId=8791&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Madison Hotel Reviews ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg) ### New Haven Hotel 10/10 Excellent "Enjoyed the room how close it was to restaurants and museums. The staff was wonderful. Will stay again!" [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg) ### Omni New Haven Hotel at Yale 10/10 Excellent "Great traditional New Haven Hotel. From check in to check out staff was very professional and welcoming. Great job for all of your staff." [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg) ### Motel 6 New Haven - Branford, CT 10/10 Excellent "Clean room" [](https://expedia.ca/New-Haven-Hotels-Motel-6-New-Haven-Branford.h50320.Hotel-Information) ![La Quinta Inn & Suites by Wyndham New Haven](https://images.trvl-media.com/lodging/1000000/10000/1300/1241/dbc425d9_y.jpg) ### La Quinta Inn & Suites by Wyndham New Haven 10/10 Excellent "Very clean room and an especially kind Front Desk team. " [](https://expedia.ca/New-Haven-Hotels-La-Quinta-Inn-Suites-By-Wyndham-New-Haven.h1241.Hotel-Information) ![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg) ### Madison Beach Hotel 10/10 Excellent "beautiful room and views" [](https://expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Holiday family tradition!" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Holiday Inn Cheshire - Southington by IHG](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/a3c0d287_y.jpg) ### Holiday Inn Cheshire - Southington by IHG 10/10 Excellent "We had a wonderful stay at the hotel. However we pre paid for breakfast and lunch and didn’t receive it for our stay." [](https://expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Hamden Hotel and Suites – Hamden New Haven](https://images.trvl-media.com/lodging/1000000/20000/18000/17931/c3c836db_y.jpg) ### Hamden Hotel and Suites – Hamden New Haven 10/10 Excellent "The stay was ok" [](https://expedia.ca/New-Haven-Hotels-Clarion-Hotel-Suites-Hamden-New-Haven.h17931.Hotel-Information) ![Comfort Inn Wethersfield - Hartford](https://images.trvl-media.com/lodging/1000000/20000/17700/17635/13705d6b_y.jpg) ### Comfort Inn Wethersfield - Hartford 8/10 Good "Nice staff. Bed was comfortable " [](https://expedia.ca/Hartford-Hotels-Comfort-Inn-Wethersfield-Hartford.h17635.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Madison? ### How many historical hotels are there in Madison? ### What are the must-see historical sites and other places to visit in Madison? ### What is a historic hotel like in Madison? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Madison have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Guilford ](https://www.expedia.ca/4Star-Guilford-Hotels.s40-0-d183062.Travel-Guide-Filter-Hotels) - [Hotels near Chamard Vineyards ](https://www.expedia.ca/Chamard-Vineyards-Hotels.0-l6309929-0.Travel-Guide-Filter-Hotels) - [B&B in Chester ](https://www.expedia.ca/Chester-Bed-And-Breakfast.d183058-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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