Best Resorts in Winchester

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Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

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
$119 nightly
The price is $137
Dec 21 - Dec 22
Total with taxes and fees
Home2 Suites by Hilton Bristol
Desk, free cribs/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, (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
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
$87 nightly
The price is $100
Dec 28 - Dec 29
Total with taxes and fees
Fairfield Inn & Suites by Marriott Plainville
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
$105 nightly
The price is $121
Dec 10 - Dec 11
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Deluxe Studio, Multiple Beds, Non Smoking | 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, (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
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

2.5 star property
Farmington
8.8 out of 10, Excellent, (1004)
"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

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
Property grounds
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 10 - Dec 11
Total with taxes and fees
Truman Gillet House Bed & Breakfast
Interior
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 star property
Avon
8.4 out of 10, Very Good, (1005)
"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
Interior
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
$75 nightly
The price is $87
Dec 16 - Dec 17
Total with taxes and fees
PLYMOUTH MOTOR LODGE
Seasonal outdoor pool, pool umbrellas, sun loungers
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
Exterior
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.
$301 nightly
The price is $345
Dec 10 - Dec 11
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Staircase
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
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
$164 nightly
The price is $189
Dec 10 - Dec 11
Total with taxes and fees
Blackberry River Inn
Exterior
Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds

Torrington
10.0 out of 10, Exceptional, (4)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
$333 nightly
The price is $383
Dec 10 - Dec 11
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
Porch
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
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
$217 nightly
The price is $250
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Abner Hotel
Front of property
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 10 - Dec 11
Total with taxes and fees
Simsbury 1820 House
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
$139 nightly
The price is $159
Jan 1 - Jan 2, 2026
Total with taxes and fees
DoubleTree by Hilton Hotel Bristol, Connecticut
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
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
$153 nightly
The price is $171
Dec 10 - Dec 11
Total with taxes and fees
Wilder House Berkshires
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 1 day ago
Sheraton Hartford Hotel at Bradley Airport

Find out more about Winchester

Winchester Resorts information

Number of reviews
10,690
Accommodation
1 Resorts
Lowest Price
$87
Highest Price
$383

Frequently asked questions

What is Winchester like for a resort vacation?
Longing for a relaxing escape? Indulge in all the comforts of a resort, where you can find everything you want for your trip from convenient dining options to activities and shopping. Browse the resorts in the area and discover the right one for you, whether you envision yourself sipping drinks by a sprawling pool or checking out the on-site boutiques.
What's a top resort for my stay in Winchester?
Our top-rated resort near Winchester: Lakeview Cottage with Dock, Kayaks - 17 mi (27.3 km) from Winchester.
What can I do in Winchester?
Discover the shopping possibilities at Ledgebrook Plaza, or bring the kids to Action Wildlife Foundation for some family fun. Additional attractions in the area include Highland Lake and The Marina at Highland Lake.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What's the best way to get to and around Winchester?
Fly into Bradley Intl. Airport (BDL), which is located 21.9 mi (35.2 km) away from the heart of the city. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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