Winchester Hotels from S$117

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7 Dec - 8 Dec
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12 Dec - 14 Dec
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Top 10 trending Winchester hotels

Desk, iron/ironing board, free WiFi, bed sheets
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 star property
Farmington
8.0 out of 10, Very good, (1006)
"Clean room with a good bed, good shower and an excellent TV "
United States
Lester
The price is S$118
includes taxes & fees
14 Dec - 15 Dec
Extended Stay America Suites Hartford Farmington
Exterior
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

2.5 star property
Farmington
8.8 out of 10, Excellent, (1002)
"Clean room and great staff"
United States
Beth
The price is S$161
includes taxes & fees
20 Dec - 21 Dec
Hampton Inn & Suites Hartford/Farmington
Lobby
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

4.0 star property
Bristol
9.0 out of 10, Wonderful, (1002)
"Amazing stay"
United States
Marquise
The price is S$207
includes taxes & fees
1 Jan - 2 Jan, 2026
DoubleTree by Hilton Hotel Bristol, Connecticut
Exterior
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

3.0 star property
Bristol
9.6 out of 10, Exceptional, (163)
"I would stay here again! "
United States
Jael
The price is S$178
includes taxes & fees
21 Dec - 22 Dec
Home2 Suites by Hilton Bristol
Desk, free cots/infant beds, rollaway beds, free WiFi
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

2.0 star property
Torrington
7.4 out of 10, Good, (1002)
"Clean comfortable room,great parking and local shopping "
United States
Julie
The price is S$125
includes taxes & fees
9 Dec - 10 Dec
Days Inn by Wyndham Torrington
BBQ/picnic Area
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

3.0 star property
Farmington
8.4 out of 10, Very good, (1003)
"Check-in was easy and the front desk person was friendly. The room is clean and well stocked with everything we need."
United States
Catherine
The price is S$162
includes taxes & fees
4 Jan - 5 Jan, 2026
Homewood Suites by Hilton Hartford-Farmington
Interior
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 star property
Avon
8.4 out of 10, Very good, (1004)
"Very nice place to stay"
United States
Alvero
The price is S$221
includes taxes & fees
9 Dec - 10 Dec
Avon Old Farms Hotel
Seasonal outdoor pool, pool umbrellas, pool loungers
Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon

3.0 star property
Avon
8.8 out of 10, Excellent, (409)
"Good hotel but expensive "
United States
Christopher
The price is S$176
includes taxes & fees
28 Dec - 29 Dec
Residence Inn by Marriott Hartford Avon
Couples treatment room(s), steam room, body treatments, aromatherapy
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

5.0 star property
Washington
9.2 out of 10, Wonderful, (55)
"Incredible place - will definitely return. "
United States
Andrew
The price is S$919
includes taxes & fees
11 Dec - 12 Dec
Mayflower Inn & Spa, Auberge Collection
Executive lounge
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1002)
"Great hotel, comfy bed and convenient."
United States
Kelly
The price is S$341
includes taxes & fees
1 Jan - 2 Jan, 2026
Sheraton Hartford Hotel at Bradley Airport
Lobby sitting area
The Litchfield Inn

The Litchfield Inn

4.0 star property
Litchfield
9.0 out of 10, Wonderful, (958)
"Quiet and so much space to lounge around in front of fireplaces. Relaxing private & was just the perfect get away!"
United States
Holly
The price is S$327
includes taxes & fees
18 Dec - 19 Dec
The Litchfield Inn
Exterior
Simsbury Inn

Simsbury Inn

3.5 star property
Simsbury Center
9.2 out of 10, Wonderful, (279)
"I loved my stay there. Beautiful rooms, the hot tub was great! Breakfast was decent but there are plenty of food options around town if you want something better!"
United States
Caitlin
The price is S$459
includes taxes & fees
9 Dec - 10 Dec
Simsbury Inn
Lobby
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

2.5 star property
Plainville
8.6 out of 10, Excellent, (908)
"Yes, the room was clean. Staff was very nice and we look forward to our next stay"
United States
Liza Marie
The price is S$130
includes taxes & fees
28 Dec - 29 Dec
Fairfield Inn & Suites by Marriott Plainville
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (163)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is S$245
includes taxes & fees
9 Dec - 10 Dec
Blackberry River Inn
Staircase
The Farmington Inn & Suites

The Farmington Inn & Suites

3.0 star property
Farmington
8.8 out of 10, Excellent, (1006)
"Tip quality, charming place to stay."
United States
Nello
The price is S$169
includes taxes & fees
22 Dec - 23 Dec
The Farmington Inn & Suites
Terrace/patio
The Abner Hotel

The Abner Hotel

3.0 star property
Litchfield Historic District
9.2 out of 10, Wonderful, (46)
"Spacious room and friendly staff "
United States
Frank
The price is S$324
includes taxes & fees
4 Jan - 5 Jan, 2026
The Abner Hotel
Lunch and dinner served
Delamar West Hartford

Delamar West Hartford

4.0 star property
West Hartford
9.8 out of 10, Exceptional, (1000)
"Fabulous and roomy. So clean so nice. Lovely humans. "
United States
Debbie
The price is S$402
includes taxes & fees
14 Dec - 15 Dec
Delamar West Hartford
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 star property
Lakeville
8.2 out of 10, Very good, (270)
"The staff is courteous and accommodating especially the restaurant staff."
United States
Christian
The price is S$314
includes taxes & fees
15 Dec - 16 Dec
Interlaken Inn & Resort
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Cornwall Inn and Lodge

Cornwall Inn and Lodge

3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (155)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is S$315
includes taxes & fees
9 Dec - 10 Dec
Cornwall Inn and Lodge
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is S$156
includes taxes & fees
9 Dec - 10 Dec
Locust Tree Bed and Breakfast LLC
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.
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Stay near popular Winchester attractions

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.
See properties

The Marina at Highland Lake

Explore the waterfront in Winchester with a trip to The Marina at Highland Lake.
See properties

Top Winchester Hotel Reviews

Simsbury Inn

Simsbury Inn

10/10 Excellent
"Simsbury Inn never disappoints. We always stay there when we're in the area. A wonderful staff that gives you a warm welcome upon arrival. They are available 24/7 and very accommodating. A beautiful property with lots of amenities. Excellent location, very clean and a great breakfast. Highly recommend."
Cheryl 4-night trip
Posted 2 days ago
Simsbury Inn

More cheap stays in Winchester

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT
The price is S$118 per night from 14 Dec to 15 Dec
S$118
14 Dec - 15 Dec
includes taxes & fees
7.8/10 Good! (999 reviews)

Frequently asked questions

What's the best place for a stay in Winchester?
Extended Stay America Suites Hartford Farmington, located 22.6 mi (36.3 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 Avon Old Farms Hotel. 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: Features a sauna, a seasonal outdoor pool and buffet. Hampton Inn & Suites Hartford/Farmington and Homewood Suites by Hilton Hartford-Farmington 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 17 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, The Marina at Highland Lake and Winchester Historical Society. A couple of additional sights to add to your itinerary are Burr Pond State Park 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.

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