Photo by Kim Knox Beckius
Winsted Hotels
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Winsted
Check prices for these dates
Our top choices for Winsted hotels
9.2 out of 10, Wonderful, (1004)
Immerse yourself in the historic charm of this restored inn, offering a peaceful atmosphere with an indoor pool and fitness centre. Enjoy free breakfast, then explore nearby attractions or rent bikes to discover the area's vineyards and performing arts venues.
"Friendly, welcoming, and helpful staff. The room was beautiful and clean. The bar and restaurant were cozy; drinks and food delicious. "
Christina
The price is €170
includes taxes & fees
6 Jan - 7 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
8.8 out of 10, Excellent, (714)
Experience comfort in Great Barrington at this welcoming hotel with clean rooms and attentive service. Visit nearby Lake Mansfield Park or explore the Housatonic River after enjoying the indoor pool, fitness centre, and complimentary WiFi.
"We stay here every year and it never disappoints "
Elizabeth
The price is €93
includes taxes & fees
25 Jan - 26 Jan 2026
8.4 out of 10, Very good, (819)
Located in Westfield, this hotel offers a complimentary breakfast that guests rave about. Take a refreshing dip in the indoor pool, work out in the fitness centre, or visit nearby General Wareham Park. Free WiFi and parking add convenience.
"Very pet friendly and the night check in agent was super kind and friendly"
olivia townsend
The price is €111
includes taxes & fees
21 Jan - 22 Jan 2026
9.0 out of 10, Wonderful, (811)
"Yes it was clean & staff was very polite. "
Barbara L.
8.4 out of 10, Very good, (1000)
Set in a serene location near Housatonic River Walk, this hotel offers free breakfast, WiFi, and parking. Enjoy the fitness centre or explore nearby trails for hiking and skiing. Guests praise the helpful staff and quiet atmosphere in this convenient Great Barrington retreat.
"My go to place for my ski weekends"
Ryan
The price is €72
includes taxes & fees
13 Jan - 14 Jan 2026
8.6 out of 10, Excellent, (548)
Surrounded by natural attractions like Monument Mountain, this welcoming motel offers complimentary WiFi and parking. Daily housekeeping ensures comfort while the attentive staff enhances every stay in this charming Berkshires location.
"Perfect for pets "
Maria
The price is €104
includes taxes & fees
1 Jan - 2 Jan 2026
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.
Save an average of 15% on thousands of hotels when you're signed in
Stay near popular Winsted attractions
Learn more about Winsted
Highland Lake offers refreshing swimming and boating during summer months, with a small beach perfect for families. Explore the American Museum of Tort Law founded by Ralph Nader, then grab coffee at one of Main Street's welcoming cafes.
Photo by Kim Knox Beckius
Open Photo by Kim Knox Beckius
More cheap stays in Winsted
Extended Stay America Suites Hartford Farmington
1 Batterson Park Rd Farmington CT
The price is €73 per night from 4 Jan to 5 Jan
€73
4 Jan - 5 Jan 2026
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Frequently asked questions
Explore a world of travel with Expedia
- 3 Star Hotels in Lime Rock
- Avon Hotels
- Bethlehem Hotels
- Bloomfield Hotels
- Hotels near Bradley Intl.
- Bristol Hotels
- Burlington Hotels
- Canaan Hotels
- Canton Hotels
- Hotels near Central Connecticut State University
- Cottages in Colebrook
- Apartments in Connecticut
- Villas in Connecticut
- Hotels near Copernican Observatory & Planetarium
- Beach Hotels in Connecticut
- Hotels with Restaurant in Connecticut
- Downtown Hartford Hotels
- Cheap Hotels in Farmington
- Farmington Hotels
- Granby Hotels
- Hotels near Harney and Sons Tea Tasting Room
- Cheap Hotels in Hartford
- Hartford Hotels
- Hotels near Lake Compounce
- Lime Rock Hotels
- Hotels near Mohawk Mountain Ski Area
- Hotels with Spa in Norfolk
- Norfolk Hotels
- Plainville Hotels
- Salisbury Hotels
- Sharon Hotels
- Simsbury Hotels
- Torrington Hotels
- Caravan Parks in Warren
- Warren Hotels
- Watertown Hotels
- West Cornwall Hotels
- West Hartford Hotels
- West Simsbury Hotels
- Windsor Locks Hotels
- Flights to Bradley Intl.
- Flights to Hartford
- Flights to Torrington
- Flights to Windsor Locks
- Flights from Bradley Intl.
- Flights from Izmir (ADB) to Hartford (BDL)
- Flights from Boston (BOS) to Hartford (BDL)
- Flights from Dublin (DUB) to Hartford (BDL)
- Flights from Newark Liberty Intl. Airport (EWR) to Hartford (BDL)
- Flights from New York (JFK) to Hartford (BDL)
- Flights from London (LHR) to Hartford (BDL)
- Flights from Orlando (MCO) to Hartford (BDL)
- Flights from Nador (NDR) to Hartford (BDL)
- Flights from Philadelphia (PHL) to Hartford (BDL)
- Flights from Poughkeepsie (POU) to Hartford (BDL)
- Flights from Seattle (SEA) to Hartford (BDL)
- Flights from Seward (SWD) to Hartford (BDL)
- Flights from Villavicencio (VVC) to Hartford (BDL)
- Flights from Toronto (YYZ) to Hartford (BDL)
- Alamo Rent A Car Rental Cars in Bradley Intl.
- Avis Rental Cars in Bradley Intl.
- Budget Rental Cars in Bradley Intl.
- Car hire Avon
- Rental cars Bradley Intl. airport
- Car hire Hartford
- Compact Car Hire near Bradley Intl.
- Dollar Rent A Car Rental Cars in Bradley Intl.
- Drive-A-Matic Rental Cars in Bradley Intl.
- Enterprise Rental Cars in Bradley Intl.
- First Car Rental Rental Cars in Bradley Intl.
- Fox Rental Cars Rental Cars in Bradley Intl.
- Hertz Rental Cars in Bradley Intl.
- Luxury Car Hire near Bradley Intl.
- National Car Rental Rental Cars in Bradley Intl.
- Ok Mobility Rental Cars in Bradley Intl.
- Payless Rental Cars in Bradley Intl.
- Pickup Car Hire near Bradley Intl.
- Right-Cars Rental Cars in Bradley Intl.
- Sixt Rental Cars in Bradley Intl.
- Suv Car Hire near Bradley Intl.
- Thrifty Car Rental Rental Cars in Bradley Intl.
- Top Rent a Car Rental Cars in Bradley Intl.
- People Carrier Car Hire near Bradley Intl.
