Search Winchester hotels
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Winchester
Family friendly
Check prices for these dates
Our top choices for Winchester hotels
Truman Gillet House Bed & Breakfast
Truman Gillet House Bed & BreakfastGranby
9.6 out of 10, Exceptional, (113 reviews)
"Cute place. Antiquey Excellent breakfast!"
Valerie
The price is NZ$270
includes taxes & fees
26 July - 27 July
Wilder House Berkshires
Wilder House BerkshiresSheffield
9.8 out of 10, Exceptional, (57 reviews)
"Great stay and the breakfast was fantastic"
Jennifer
The price is NZ$310
includes taxes & fees
19 July - 20 July
Blackberry River Inn
Blackberry River InnNorfolk
9.4 out of 10, Exceptional, (193 reviews)
"Excellent breakfast, very nice staff."
Leslie
The price is NZ$277
includes taxes & fees
19 July - 20 July
Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLCEast Canaan
8.8 out of 10, Excellent, (433 reviews)
"Below average B&B"
Larry
The price is NZ$210
includes taxes & fees
1 Aug - 2 Aug
Home2 Suites by Hilton Bristol
Home2 Suites by Hilton BristolBristol
9.6 out of 10, Exceptional, (241 reviews)
"Overall good stay"
Susan
The price is NZ$291
includes taxes & fees
2 Aug - 3 Aug
Days Inn by Wyndham Torrington
Days Inn by Wyndham TorringtonTorrington
7.4 out of 10, Good, (1,007 reviews)
"Was clean, didn't smell weird and was exactly what we were looking for, just a place to sleep while our home was being repaired, no complaints at all."
Graeme
The price is NZ$204
includes taxes & fees
12 Aug - 13 Aug
The Abner Hotel
The Abner HotelLitchfield Historic District
9.6 out of 10, Exceptional, (75 reviews)
"Great place! People are AWESOME!!!"
Lisa
The price is NZ$468
includes taxes & fees
15 July - 16 July
PLYMOUTH MOTOR LODGE
PLYMOUTH MOTOR LODGETerryville
7.8 out of 10, Good, (198 reviews)
"Everything was nice! I'd stay here again!"
SEMORA
The price is NZ$163
includes taxes & fees
5 Aug - 6 Aug
Hitching Post Country Motel
Hitching Post Country MotelCornwall Bridge
6.8 out of 10, (98 reviews)
"Clean...cheap and comfortable bed"
leo
The price is NZ$259
includes taxes & fees
25 July - 26 July
The Millerton Inn
The Millerton InnMillerton
8.4 out of 10, Very good, (32 reviews)
"We had a beautiful experience, staff was very accommodating."
Bernadette
The price is NZ$493
includes taxes & fees
23 July - 24 July
The Farmington Inn & Suites
The Farmington Inn & SuitesFarmington
8.8 out of 10, Excellent, (1,001 reviews)
"Wonderful breakfast and great staff."
Carol
The price is NZ$408
includes taxes & fees
16 July - 17 July
Sunny Peace Homestay
Sunny Peace HomestayHarwinton
9.4 out of 10, Exceptional, (9 reviews)
"Angela is very respectful and generous to her guests."
Jean
The price is NZ$346
includes taxes & fees
7 Aug - 8 Aug
Sheraton Hartford Hotel at Bradley Airport
Sheraton Hartford Hotel at Bradley AirportWindsor Locks
9.2 out of 10, Wonderful, (1,007 reviews)
"Great location right outside the airport. Food reasonably priced and delicious."
Stacy
The price is NZ$458
includes taxes & fees
9 Aug - 10 Aug
Simsbury 1820 House
Simsbury 1820 HouseSimsbury Center
9.4 out of 10, Exceptional, (1,002 reviews)
"Beautiful historical hotel
Room was lovely
Staff friendly and helpful"
FRANK
The price is NZ$408
includes taxes & fees
15 July - 16 July
Hampton Inn & Suites Hartford/Farmington
Hampton Inn & Suites Hartford/FarmingtonFarmington
9.0 out of 10, Wonderful, (1,012 reviews)
"Great stay and would definitely be back to stay again"
Mary Melissa
The price is NZ$244
includes taxes & fees
2 Aug - 3 Aug
Extended Stay America Suites Hartford Farmington
Extended Stay America Suites Hartford FarmingtonFarmington
8.0 out of 10, Very good, (1,001 reviews)
"Room was clean and location in good area"
Keith
The price is NZ$224
includes taxes & fees
2 Aug - 3 Aug
Cornwall Inn and Lodge
Cornwall Inn and LodgeCornwall Bridge
9.2 out of 10, Wonderful, (166 reviews)
"A charming stopover on our weekend travels. Small, quiet and lovely. Nice conversation with the host over breakfast too."
Janice
The price is NZ$423
includes taxes & fees
19 July - 20 July
The Litchfield Inn
The Litchfield InnLitchfield
9.2 out of 10, Wonderful, (1,004 reviews)
"Staff were all very friendly and helpful. Breakfast was great!"
Evan
The price is NZ$582
includes taxes & fees
27 July - 28 July
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 Winchester attractions
Top Winchester Hotel Reviews
Recent Reviews in Winchester
Home2 Suites by Hilton Bristol
8/10 Good
More cheap accommodation in Winchester
PLYMOUTH MOTOR LODGE
325 Main St Terryville CT
The price is NZ$163 per night from 5 Aug to 6 Aug
NZ$163
5 Aug - 6 Aug
includes taxes & fees
7.8/10 Good! (198 reviews)
Frequently asked questions
Explore a world of travel with Expedia
- Winery Hotels in Litchfield
- Luxury Hotels in Litchfield
- Family Hotels in Connecticut
- Cheap Hotels in Connecticut
- Luxury Hotels in Connecticut
- Historic Hotels in Torrington
- Apartments in Riverton
- Guest Houses in Goshen
- B&B in Lime Rock
- Apartments in Lakeville
- Motels in Bristol
- B&B in Sharon
- Cottages in New Preston
- B&B in Torrington
- Caravan Parks in Morris
- Cottages in Connecticut
- Motels in Connecticut
- Holiday Homes in Connecticut
- Apartments in Connecticut
- Farmstay in Colebrook
- Marriott Hotels & Resorts in Bantam
- Bristol Hotels
- Warren Hotels
- Hotels near University of Connecticut-Hartford
- Morris Hotels
- Hartford County Hotels
- Norfolk Hotels
- Hotels near Lake Waramaug State Park
- Torrington Hotels
- Bethlehem Hotels
- Granby Hotels
- Farmington Hotels
- Burlington Hotels
- Avon Hotels
- Hotels near Warner Theater
- Goshen Hotels
- Cornwall Hotels
- Canton Hotels
- Salisbury Hotels
- Hotels near Elizabeth Park
- Hotels near Bradley Intl.
- Wolcott Hotels
- Litchfield Hotels
- Bloomfield Hotels
- Riverton Hotels
- West Cornwall Hotels
- West Hartford Hotels
- Harwinton Hotels
- Plymouth Hotels
- Sharon Hotels
- Bantam Hotels
- Flights to Granby
- Flights to Torrington
- Flights from Bradley Intl.
- Flights from Bristol
- Flights from Goshen
- Flights from West Hartford
- Flights from East Hartland
- Flights from Sharon
- Flights from Terryville
- Flights from Washington (IAD) to Hartford (BDL)
- Flights from St. Moritz (SMV) to Hartford (BDL)
- Flights from San Francisco (SFO) to Hartford (BDL)
- Flights from Auckland (AKL) to Hartford (BDL)
- Flights from Westfield (BAF) to Hartford (BDL)
- Flights from Orlando (MCO) to Hartford (BDL)
- Flights from SĆ£o TomĆ© Island (TMS) to Hartford (BDL)
- Flights from Seattle (SEA) to Hartford (BDL)
- Flights from Gap (GAT) to Hartford (BDL)
- Flights from San Diego (SAN) to Hartford (BDL)
- Flights from Kitchener (YKF) to Hartford (BDL)
- Flights from Dallas (DFW) to Hartford (BDL)
- Visit Canton
- Visit Lime Rock
- Visit Unionville
- Visit Morris
- Visit Bantam
- Visit New Preston
- Visit Salisbury
- Visit Torrington
- Visit Bethlehem Village
- Visit Falls Village
- Flamig Farm
- Bantam Holidays
- Bristol Public Library
- Rosedale Farms & Vineyards
- Connecticut Holidays
- Warner Theater
- Miranda Vineyard
- Bethlehem Holidays
- Car hire near Harney and Sons Tea Tasting Room
- Rental cars Bradley Intl. airport
- Sports Car Car Hire near Bradley Intl.
- Luxury Car Hire near Bradley Intl.
- Thrifty Car Rental Rental Cars in Bradley Intl.
- Alamo Rent A Car Rental Cars in Bradley Intl.
- Payless Rental Cars in Connecticut
- Europcar Rental Cars in City Meadow Boardwalk
