Find hotels in Winchester, CT from ฿3,176

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (416 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is ฿3,411
฿3,923 total
includes taxes & fees
28 Apr - 29 Apr
Locust Tree Bed and Breakfast LLC

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (105 reviews)
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
The price is ฿4,548
฿5,049 total
includes taxes & fees
25 Apr - 26 Apr
Truman Gillet House Bed & Breakfast

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (45 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is ฿5,228
฿5,840 total
includes taxes & fees
26 Apr - 27 Apr
Wilder House Berkshires

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (214 reviews)
"Great place for a quick family getaway!!"
United States
Rosemary
The price is ฿4,841
฿5,567 total
includes taxes & fees
20 May - 21 May
Home2 Suites by Hilton Bristol

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,000 reviews)
"Parking was great, staff very helpful, and the room was really clean. "
United States
Enrisa
The price is ฿2,816
฿3,239 total
includes taxes & fees
3 May - 4 May
Days Inn by Wyndham Torrington

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (187 reviews)
"Staff was very rude.The owner was very rude.We'll never stay there again"
United States
Jeff
The price is ฿2,761
฿3,176 total
includes taxes & fees
3 May - 4 May
PLYMOUTH MOTOR LODGE

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (173 reviews)
"Charming, quiet, clean very clean with a beautiful dining room for breakfast and very respectful service."
United States
Mara
The price is ฿5,058
฿5,817 total
includes taxes & fees
26 Apr - 27 Apr
Blackberry River Inn

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very good, (18 reviews)
"Nice staff, great restaurant at the inn. Very cute town. "
United States
Valerie
The price is ฿8,158
฿9,228 total
includes taxes & fees
27 Apr - 28 Apr
The Millerton Inn

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (83 reviews)
"Checkin was easy, room was clean and comfortable "
United States
Greg
The price is ฿4,223
฿4,857 total
includes taxes & fees
25 Apr - 26 Apr
Hitching Post Country Motel

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (136 reviews)
"Beautiful property and rooms."
United States
Kara
The price is ฿5,022
฿5,509 total
includes taxes & fees
14 May - 15 May
Gedney Farm

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection
5.0 star property
Washington
9.4 out of 10, Exceptional, (59 reviews)
"Clean room "
United States
Casey
The price is ฿22,660
฿27,944 total
includes taxes & fees
28 Apr - 29 Apr
Mayflower Inn & Spa, Auberge Collection

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,004 reviews)
"Lovely stay!"
United States
Ilana
The price is ฿4,369
฿5,585 total
includes taxes & fees
5 May - 6 May
The Farmington Inn & Suites

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very good, (1,003 reviews)
"Beautiful spot! Very clean ❤️"
Canada
Peggy
The price is ฿3,671
฿4,221 total
includes taxes & fees
26 Apr - 27 Apr
Extended Stay America Suites Hartford Farmington

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (158 reviews)
"We stay here frequently…always super clean and the inn keepers are very kind."
United States
Tracy
The price is ฿6,874
฿7,906 total
includes taxes & fees
25 Apr - 26 Apr
Cornwall Inn and Lodge

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (58 reviews)
"This hotel was absolutely beautiful, the staff was so helpful and attentive. We will definitely be back on our next stay in Litchfield. "
United States
Jessica
The price is ฿9,625
฿11,068 total
includes taxes & fees
27 Apr - 28 Apr
The Abner Hotel

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1,004 reviews)
"Clean room, friendly staff and quiet grounds."
United States
shaneice
The price is ฿4,555
฿5,239 total
includes taxes & fees
18 May - 19 May
Hampton Inn & Suites Hartford/Farmington

9 Academy

9 Academy
4.0 star property
Salisbury
9.2 out of 10, Wonderful, (12 reviews)
"Extremely clean and the rooms are beautifully decorated with warm minimal decor. We will definitely be back!"
United States
Gina
The price is ฿17,868
฿20,549 total
includes taxes & fees
25 Apr - 26 Apr
9 Academy

Dainty New Preston Cottage w/ Dock & Lake Views!

Dainty New Preston Cottage w/ Dock & Lake Views!
3.0 star property
New Preston
The price is ฿6,952
฿16,793 total
includes taxes & fees
26 Apr - 27 Apr
Dainty New Preston Cottage w/ Dock & Lake Views!

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,000 reviews)
"The stay was great, very accommodating staff, quaint rooms and lounge area!"
United States
Cathy
The price is ฿5,907
฿7,353 total
includes taxes & fees
26 Apr - 27 Apr
Simsbury 1820 House

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (963 reviews)
"Average clean rooms, pool small, pizza Resterant good. Staff great at hotel and Resterant. "
United States
Kellie
The price is ฿3,541
฿4,072 total
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites by Marriott Plainville
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

More cheap stays in Winchester

Frequently asked questions

What's the best place for a stay in Winchester?
The Farmington Inn & Suites, located 20.6 mi (33.1 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Two other choices for your stay in the area are Sheraton Hartford Hotel at Bradley Airport and Delamar West Hartford. See all available top hotels, or vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, most hotel bookings are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What are some hotels with pools in Winchester?
Avon Old Farms Hotel: Offers a sauna, a seasonal outdoor pool and buffet. Hampton Inn & Suites Hartford/Farmington and Fairfield Inn & Suites by Marriott Plainville are two additional hotels with an on-site pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester will definitely find plenty to explore and enjoy. In Winchester, there are 16 hotels and other accommodation options to choose from. Find out more about Winchester.
What should I see while I'm in Winchester?
Favourite places to visit include Highland Lake, Burr Pond State Park and The Marina at Highland Lake. A couple of additional sights to add to your itinerary are Winchester Historical Society and Platt Hill State Park. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the seasonal weather in Winchester?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 15 cm of snowfall.