Winchester Chalets

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Exterior
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1003)
"Clean comfortable room,great parking and local shopping "
United States
Julie
$84 nightly
The price is $97
Dec 14 - Dec 15
Total with taxes and fees
Days Inn by Wyndham Torrington
Exterior
Home2 Suites by Hilton Bristol

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
$119 nightly
The price is $137
Dec 21 - Dec 22
Total with taxes and fees
Home2 Suites by Hilton Bristol
Aerial view
Locust Tree Bed and Breakfast LLC

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
$105 nightly
The price is $121
Dec 11 - Dec 12
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
View from property
Fairfield Inn & Suites by Marriott Plainville

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
$87 nightly
The price is $100
Dec 28 - Dec 29
Total with taxes and fees
Fairfield Inn & Suites by Marriott Plainville
Property grounds
Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (101)
"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
$140 nightly
The price is $155
Dec 11 - Dec 12
Total with taxes and fees
Truman Gillet House Bed & Breakfast
Exterior
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1000)
"Clean room and great staff"
United States
Beth
$108 nightly
The price is $124
Dec 20 - Dec 21
Total with taxes and fees
Hampton Inn & Suites Hartford/Farmington
BBQ/picnic area
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
3.0 star property
Farmington
8.4 out of 10, Very Good, (1000)
"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
$109 nightly
The price is $125
Jan 4 - Jan 5, 2026
Total with taxes and fees
Homewood Suites by Hilton Hartford-Farmington
Exterior
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very Good, (1002)
"Clean room with a good bed, good shower and an excellent TV "
United States
Lester
$81 nightly
The price is $93
Dec 21 - Dec 22
Total with taxes and fees
Extended Stay America Suites Hartford Farmington
Exterior
Avon Old Farms Hotel

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1000)
"Very nice place to stay"
United States
Alvero
$118 nightly
The price is $136
Dec 28 - Dec 29
Total with taxes and fees
Avon Old Farms Hotel
Exterior
Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (410)
"Good hotel but expensive "
United States
Christopher
$110 nightly
The price is $126
Dec 21 - Dec 22
Total with taxes and fees
Residence Inn by Marriott Hartford Avon
Front of property - evening/night
PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (178)
"Good basic room, squeeky beds and the bathroom faucets doesnt turn off. Good value though for $103.50"
United States
David
$74 nightly
The price is $86
Dec 14 - Dec 15
Total with taxes and fees
PLYMOUTH MOTOR LODGE
Exterior
The Farmington Inn & Suites

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1001)
"Tip quality, charming place to stay."
United States
Nello
$110 nightly
The price is $127
Dec 29 - Dec 30
Total with taxes and fees
The Farmington Inn & Suites
Front of property
Blackberry River Inn

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
$164 nightly
The price is $189
Dec 15 - Dec 16
Total with taxes and fees
Blackberry River Inn
Terrace/patio
The Abner Hotel

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
$217 nightly
The price is $250
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Abner Hotel
Exterior
DoubleTree by Hilton Hotel Bristol, Connecticut

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
$139 nightly
The price is $159
Jan 1 - Jan 2, 2026
Total with taxes and fees
DoubleTree by Hilton Hotel Bristol, Connecticut
Balcony
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (270)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
$237 nightly
The price is $273
Jan 8 - Jan 9, 2026
Total with taxes and fees
Interlaken Inn & Resort
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Torrington
9.6 out of 10, Exceptional, (4)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
$298 nightly
The price is $342
Dec 11 - Dec 12
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Exterior
Wilder House Berkshires

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
$151 nightly
The price is $169
Dec 17 - Dec 18
Total with taxes and fees
Wilder House Berkshires
Front of property
Simsbury 1820 House

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1000)
"Very nice room, pleasant and helpful staff"
United States
Concetta
$174 nightly
The price is $200
Dec 11 - Dec 12
Total with taxes and fees
Simsbury 1820 House
Property grounds
Peaceful Meadow Retreat

Peaceful Meadow Retreat

Peaceful Meadow Retreat
2.0 star property
Granby
10.0 out of 10, Exceptional, (16)
"The place is beautiful and very quiet and relaxing"
United States
Marian
$174 nightly
The price is $197
Jan 6 - Jan 7, 2026
Total with taxes and fees
Peaceful Meadow Retreat
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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Top Winchester Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Clean room, staff were friendly, helpful and kind. Quiet even with planes landing right next door. Can't compliment this place enough."
Christine 1-night trip
Posted 2 days ago
Sheraton Hartford Hotel at Bradley Airport

Find out more about Winchester

Winchester Chalets information

Number of reviews
10,705
Accommodation
1 Chalets
Lowest Price
$86
Highest Price
$342

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