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 detail
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Apartment in winsted

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.2 out of 10, Wonderful, (46)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
$174 nightly
The price is $196
Dec 13 - Dec 14
Total with taxes and fees
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Exterior
Days Inn by Wyndham Torrington

Motel in Torrington

Days Inn by Wyndham Torrington
2.0 star property
7.4 out of 10, Good, (1000)
"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
9.6 out of 10, Exceptional, (165)
"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

Bed & Breakfast in East Canaan

Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Dec 12 - Dec 13
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
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

Bed & Breakfast in Granby

Truman Gillet House Bed & Breakfast
3.0 star property
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 12 - Dec 13
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
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
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
The Farmington Inn & Suites

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
8.8 out of 10, Excellent, (1002)
"Tip quality, charming place to stay."
United States
Nello
$104 nightly
The price is $120
Dec 29 - Dec 30
Total with taxes and fees
The Farmington Inn & Suites
Exterior
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
8.0 out of 10, Very Good, (1001)
"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
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
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
Exterior
Wilder House Berkshires

Bed & Breakfast in Sheffield

Wilder House Berkshires
2.0 star property
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
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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 14 - Dec 15
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Front of property - evening/night
PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
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
Balcony
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
8.2 out of 10, Very Good, (270)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
$223 nightly
The price is $257
Dec 26 - Dec 27
Total with taxes and fees
Interlaken Inn & Resort
Terrace/patio
The Abner Hotel

The Abner Hotel

The Abner Hotel
3.0 star property
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
9.0 out of 10, Wonderful, (1000)
"Amazing stay"
United States
Marquise
$139 nightly
The price is $159
Dec 21 - Dec 22
Total with taxes and fees
DoubleTree by Hilton Hotel Bristol, Connecticut
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$614 nightly
The price is $629
Dec 14 - Dec 15
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Property grounds
Peaceful Meadow Retreat

Apartment in Granby

Peaceful Meadow Retreat
2.0 star property
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 3 days ago
Sheraton Hartford Hotel at Bradley Airport

Find out more about Winchester

Winchester Chalets information

Number of reviews
9,600
Accommodation
1 Chalets
Lowest Price
$86
Highest Price
$629

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