Book a Historical Hotel in Windham County

Name: Holiday Inn Express Hotel & Suites Brattleboro by IHG
Price range: $158 total

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Top cities in Windham County

We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!

Brattleboro

Love our public lands! This Army Corps campground has a clean rushing stream in the middle and mountains all around. Seasonal.

Londonderry

Featured Windham County Historic Hotels

$201 nightly

$221 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

Guests of The Wilmington Inn enjoy access to free WiFi in public areas, spa services, and coffee in a common area. Free parking is available if you drive. Front-desk staff can assist with tours/tickets and luggage storage. Other amenities at this golf bed & breakfast include a refrigerator in a common area, a meeting room, and an arcade/game room.

Breakfast included

Spa

Guests staying at Grafton Inn enjoy an outdoor pool, a gym, and outdoor tennis courts. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include free WiFi in public areas, a business center, and free use of bicycles.

Pool

Breakfast included

$235 nightly

$258 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

Guests of Inn on Putney Road enjoy access to free WiFi in public areas, a 24-hour business center, and spa services. You can take advantage of free parking, along with a free train station shuttle. Helpful staff can provide concierge services, luggage storage, and a safe deposit box at the front desk. Additional amenities include a computer station, a library, and express check-out.

Breakfast included

Spa

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$123 total

Dec 25 - Dec 26

Total with taxes and fees

At Latchis Hotel, guests have access to karaoke, free WiFi in public areas, and conference space. You can take advantage of free parking if you drive. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Additional amenities include coffee/tea in a common area, local meal delivery service, and wedding services.

Pet friendly

Parking included

$142 nightly

$157 total

Dec 25 - Dec 26

Total with taxes and fees

Colonel Williams Inn features free WiFi in public areas, coffee in a common area, and microwave in a common area. A stay here includes free parking. Helpful staff is there to provide concierge services, as well as offer insight about the area. Additional amenities include a refrigerator in a common area, a library, and a terrace.

Breakfast included

Parking included

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$132 total

Dec 25 - Dec 26

Total with taxes and fees

Guests of Colonial Motel And Spa have access to a full-service spa, 2 indoor pools, and a gym. You can put free parking to good use if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Other amenities at this spa motel include a sauna, free WiFi in public areas, and a hot tub.

Pool

Hot Tub

$159 nightly

$175 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

The Nutmeg features free WiFi in public areas, a seasonal outdoor pool, and coffee in a common area. There's free parking if you drive. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Additional amenities include an arcade/game room, a picnic area, and a garden.

Pool

Breakfast included

At Quality Inn & Conference Center, guests enjoy an indoor pool, a gym, and free WiFi in public areas. You can take advantage of free parking if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include meeting rooms, conference space, and coffee/tea in a common area.

Pool

Breakfast included

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$161 total

Dec 30 - Dec 31

Total with taxes and fees

At Hampton Inn Brattleboro, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. If you plan to drive, free parking is available. The front desk is staffed 24 hours a day to help with dry cleaning/laundry and securing valuables. Additional amenities include a hot tub, a 24-hour business center, and coffee/tea in a common area.

Pool

Hot Tub

Free Cancellation

Reserve now, pay when you stay

$53 nightly

$58 total

Dec 28 - Dec 29

Total with taxes and fees

Travelodge by Wyndham Brattleboro VT features free WiFi in public areas and a vending machine. You can take advantage of free parking if you drive. Front-desk staff are standing by 24/7 to assist with any requests.

Pet friendly

Parking included

Free Cancellation

Reserve now, pay when you stay

$117 nightly

$129 total

Dec 28 - Dec 29

Total with taxes and fees

Guests of Comfort Inn & Suites Brattleboro I-91 have access to an indoor pool, a gym, and free WiFi in public areas. There's free parking if you drive. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Additional amenities include meeting rooms, a business center, and laundry facilities.

Pool

Breakfast included

Dalem's Chalet features an outdoor pool, a gym, and a business center. You can take advantage of free parking if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include a terrace, a garden, and a reception hall.

Pool

Parking included

Riverside Hotel, an Ascend Collection Hotel

Free Cancellation

$152 nightly

$165 total

Jan 22 - Jan 23, 2026

Total with taxes and fees

At Riverside Hotel, an Ascend Collection Hotel, guests have access to a 24-hour gym, free WiFi in public areas, and a conference center. A stay here includes free parking. The 24-hour front desk has staff standing by to help with securing valuables, concierge services, and luggage storage. Additional amenities include express check-out, a terrace, and wedding services.

Parking included

Free WiFi

$110 nightly

$121 total

Dec 29 - Dec 30

Total with taxes and fees

Guests of Black Mountain Inn enjoy access to free WiFi in public areas, a seasonal outdoor pool, and coffee in a common area. A stay here includes free parking. The front desk has multilingual staff that can answer questions about the accommodations, services, and more. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include express check-out, laundry facilities, and a garden.

Pool

Breakfast included

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Free Cancellation

$144 nightly

$158 total

Dec 31 - Jan 1, 2026

Total with taxes and fees

Guests of Holiday Inn Express Hotel & Suites Brattleboro by IHG have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. You can take advantage of free parking, along with limo/town car service. Front-desk staff can answer questions 24/7, and assist with luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include meeting rooms, conference space, and a business center.

Pool

Breakfast included

Don't see what you're looking for?

See all available properties in Windham County

View all properties

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.

Uncover the Intrigue of a Windham County Historic Hotel

Featuring a variety of historic hotels, Windham County offers travelers a rich tapestry of one-of-a-kind local experiences. Whether you choose opulence or rustic charm, you can embrace life in a different era for a night, a weekend, or an extended stay.

Upgrades and restores
Historic hotels have often been painstakingly restored to reflect their original glory or to update them with a contemporary vibe. You can choose to rough it in humble historic accommodations, or experience the good life in the area's sophisticated restored mansions and original hotels.

Historic hotels allow you to embrace each hotel’s heyday. Sip drinks in a retro bar, relish a candlelit dinner in a lavish dining room, or enjoy a private fire in your own well-appointed suite.

Many historic hotels even feature original grand facades and modern interiors with newly renovated lobbies and rooms. Others have been meticulously restored to reflect every historic detail of the building’s past. Choose how you wish to experience the history of Windham County!

Get a glimpse of the past at a Windham County historic hotel
Whether you’re looking for a retro experience or you want something from a different century, a stay at a famous hotel in Windham County offers an unforgettable escape that will take your vacation to a new and unexpected level.

Discover life in Windham County from a different perspective with a trip back in time and book your historic hotel stay today.

Windham County Historic Hotels essential information

Historic Hotels in Windham County	22
Highest price	$258
Cheapest price	$58
Total number of hotels in Windham County	1,376
Popular hotels	The Wilmington Inn, Grafton Inn, Inn on Putney Road, Latchis Hotel, Colonel Williams Inn, Colonial Motel And Spa, The Nutmeg, Quality Inn & Conference Center, Hampton Inn Brattleboro, Travelodge by Wyndham Brattleboro VT, Comfort Inn & Suites Brattleboro I-91, Dalem's Chalet, Riverside Hotel, an Ascend Collection Hotel, Black Mountain Inn, Holiday Inn Express Hotel & Suites Brattleboro by IHG