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Our top choices for Winchester hotels

Truman Gillet House Bed & Breakfast
Truman Gillet House Bed & BreakfastGranby
9.6 out of 10, Exceptional, (106 reviews)
$140 nightly
The price is $155
Apr 28 - Apr 29
Total with taxes and fees

Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLCEast Canaan
9.0 out of 10, Wonderful, (417 reviews)
$105 nightly
The price is $121
Apr 28 - Apr 29
Total with taxes and fees

Wilder House Berkshires
Wilder House BerkshiresSheffield
9.8 out of 10, Exceptional, (45 reviews)
$150 nightly
The price is $168
Apr 28 - Apr 29
Total with taxes and fees

Home2 Suites by Hilton Bristol
Home2 Suites by Hilton BristolBristol
9.6 out of 10, Exceptional, (218 reviews)
$135 nightly
The price is $155
May 25 - May 26
Total with taxes and fees

Days Inn by Wyndham Torrington
Days Inn by Wyndham TorringtonTorrington
7.4 out of 10, Good, (1,000 reviews)
$82 nightly
The price is $94
May 3 - May 4
Total with taxes and fees

Blackberry River Inn
Blackberry River InnNorfolk
9.4 out of 10, Exceptional, (173 reviews)
$154 nightly
The price is $177
May 10 - May 11
Total with taxes and fees

The Farmington Inn & Suites
The Farmington Inn & SuitesFarmington
8.8 out of 10, Excellent, (1,007 reviews)
$137 nightly
The price is $158
May 5 - May 6
Total with taxes and fees

Hampton Inn & Suites Hartford/Farmington
Hampton Inn & Suites Hartford/FarmingtonFarmington
8.8 out of 10, Excellent, (1,007 reviews)
$122 nightly
The price is $141
May 25 - May 26
Total with taxes and fees

PLYMOUTH MOTOR LODGE
PLYMOUTH MOTOR LODGETerryville
7.6 out of 10, Good, (188 reviews)
$78 nightly
The price is $90
May 4 - May 5
Total with taxes and fees

The Millerton Inn
The Millerton InnMillerton
8.4 out of 10, Very Good, (18 reviews)
$237 nightly
The price is $268
Apr 28 - Apr 29
Total with taxes and fees

Extended Stay America Suites Hartford Farmington
Extended Stay America Suites Hartford FarmingtonFarmington
8.0 out of 10, Very Good, (1,005 reviews)
$115 nightly
The price is $132
May 6 - May 7
Total with taxes and fees

Cornwall Inn and Lodge
Cornwall Inn and LodgeCornwall Bridge
9.2 out of 10, Wonderful, (158 reviews)
$212 nightly
The price is $243
Apr 28 - Apr 29
Total with taxes and fees

Hitching Post Country Motel
Hitching Post Country MotelCornwall Bridge
6.6 out of 10, (83 reviews)
$130 nightly
The price is $150
Apr 28 - Apr 29
Total with taxes and fees

The Abner Hotel
The Abner HotelLitchfield Historic District
9.4 out of 10, Exceptional, (59 reviews)
$327 nightly
The price is $376
May 3 - May 4
Total with taxes and fees

Interlaken Inn & Resort
Interlaken Inn & ResortLakeville
8.2 out of 10, Very Good, (295 reviews)
$233 nightly
The price is $268
May 5 - May 6
Total with taxes and fees

The Litchfield Inn
The Litchfield InnLitchfield
9.0 out of 10, Wonderful, (985 reviews)
$254 nightly
The price is $292
Apr 28 - Apr 29
Total with taxes and fees

Mayflower Inn & Spa, Auberge Collection
Mayflower Inn & Spa, Auberge CollectionWashington
9.4 out of 10, Exceptional, (59 reviews)
$705 nightly
The price is $811
May 6 - May 7
Total with taxes and fees

Fairfield Inn & Suites by Marriott Plainville
Fairfield Inn & Suites by Marriott PlainvillePlainville
8.6 out of 10, Excellent, (967 reviews)
$96 nightly
The price is $110
May 25 - May 26
Total with taxes and fees

Simsbury 1820 House
Simsbury 1820 HouseSimsbury Center
9.2 out of 10, Wonderful, (1,001 reviews)
$190 nightly
The price is $219
Apr 28 - Apr 29
Total with taxes and fees
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
Top Winchester Hotel Reviews

Home2 Suites by Hilton Bristol
10/10 Excellent
More cheap stays in Winchester

PLYMOUTH MOTOR LODGE
325 Main St Terryville CT
$78 nightly
The price is $90 total per night from May 4 to May 5
$90 total
May 4 - May 5
Total with taxes and fees
7.6/10 Good! (188 reviews)
Hotels in Winchester with star-rating

5 Star Hotels
1 properties
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