Search Resort Hotels in Winchester from CA $125

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Check prices for these dates

Next weekend
Apr 17 - Apr 19
In two weeks
Apr 24 - Apr 26
In one month
May 8 - May 10
In two months
Jun 5 - Jun 7
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (105 reviews)
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
The price is CA $194
CA $215 total
includes taxes & fees
Apr 10 - Apr 11
Truman Gillet House Bed & Breakfast
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (416 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is CA $145
CA $167 total
includes taxes & fees
Apr 11 - Apr 12
Locust Tree Bed and Breakfast LLC
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (208 reviews)
"Great place good people decent breakfast great room service "
United States
JULES
The price is CA $180
CA $207 total
includes taxes & fees
Apr 23 - Apr 24
Home2 Suites by Hilton Bristol
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (44 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is CA $223
CA $249 total
includes taxes & fees
Apr 14 - Apr 15
Wilder House Berkshires
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, (1,001 reviews)
"Staff was very friendly, room was clean. Overall great stay, thanks!"
United States
Nathaniel
The price is CA $128
CA $148 total
includes taxes & fees
May 4 - May 5
Days Inn by Wyndham Torrington
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1,003 reviews)
"Nice clean hotel "
United States
Tiffany
The price is CA $177
CA $204 total
includes taxes & fees
Apr 16 - Apr 17
Hampton Inn & Suites Hartford/Farmington
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (173 reviews)
"Best host (Lucas) makes all the difference! Great views and delicious breakfasts. "
United States
diane
The price is CA $203
CA $233 total
includes taxes & fees
Apr 28 - Apr 29
Blackberry River Inn
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (20 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is CA $122
CA $248 total
includes taxes & fees
Apr 13 - Apr 14
Peaceful Meadow Retreat
Staircase

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,001 reviews)
"Lovely stay!"
United States
Ilana
The price is CA $190
CA $242 total
includes taxes & fees
Apr 12 - Apr 13
The Farmington Inn & Suites
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, (1,000 reviews)
"Feels like home ! Great experience! "
United States
Yong
The price is CA $139
CA $160 total
includes taxes & fees
Apr 26 - Apr 27
Extended Stay America Suites Hartford Farmington
Fridge, microwave, oven, stovetop

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
East Granby
8.6 out of 10, Excellent, (4 reviews)
"Relaxing stay"
United States
Kim M.
The price is CA $300
CA $743 total
includes taxes & fees
Apr 10 - Apr 11
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Property grounds

River Overlook - Check the view from your deck!

River Overlook - Check the view from your deck!
Collinsville
10.0 out of 10, Exceptional, (23 reviews)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
The price is CA $222
CA $417 total
includes taxes & fees
May 4 - May 5
River Overlook - Check the view from your deck!
Lobby

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (955 reviews)
"Average clean rooms, pool small, pizza Resterant good. Staff great at hotel and Resterant. "
United States
Kellie
The price is CA $145
CA $167 total
includes taxes & fees
Apr 17 - Apr 18
Fairfield Inn & Suites by Marriott Plainville
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (144 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is CA $249
CA $476 total
includes taxes & fees
Apr 15 - Apr 16
Big farmhouse in the foothills of the Berkshires
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very good, (18 reviews)
"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."
United States
Jamie
The price is CA $348
CA $393 total
includes taxes & fees
Apr 12 - Apr 13
The Millerton Inn
Porch

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (291 reviews)
"Overall great amenities and great price"
United States
Stacie
The price is CA $248
CA $285 total
includes taxes & fees
Apr 11 - Apr 12
Interlaken Inn & Resort
Porch

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection
5.0 star property
Washington
9.4 out of 10, Exceptional, (59 reviews)
"Clean room "
United States
Casey
The price is CA $910
CA $1,127 total
includes taxes & fees
Apr 13 - Apr 14
Mayflower Inn & Spa, Auberge Collection
TV

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"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.
The price is CA $119
CA $471 total
includes taxes & fees
Apr 15 - Apr 16
Cozy Attic 10 min to Llitchfield
Smart TV

Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (18 reviews)
"What a comfortable and welcoming place to stay! Great communication with the hosts, and the space had all the amenities we needed, as well as many thoughtful extra touches. Home was spotless, and tastefully decorated. Quiet neighborhood, and super easy access to downtown. Would absolutely stay here again!"
United States
Kathryn A.
The price is CA $256
CA $427 total
includes taxes & fees
Apr 30 - May 1
Pristine Cozy Walkable Downtown 2BR Getaway
Interior

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (185 reviews)
"Staff was very rude.The owner was very rude.We'll never stay there again"
United States
Jeff
The price is CA $108
CA $125 total
includes taxes & fees
May 5 - May 6
PLYMOUTH MOTOR LODGE
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

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Clean room/friendly staff. A good hotel experience "
Mary 1-night trip
Posted 2 hours ago
Avon Old Farms Hotel

Find out more about Winchester

Winchester Resorts information

Number of reviews
6,257
Accommodation
1 Resorts
Lowest Price
CA $125
Highest Price
CA $1,127

Frequently asked questions

What is Winchester like for a resort vacation?
Expedia can help you find resorts and other lodging options that offer similar services and comforts. If you're having trouble finding a resort in Winchester that meets your needs, you can use the search page filters to look for hotels, or search for properties with amenities like swimming pools or all-inclusive rates. We make it simple to book great accommodations so you can move on to creating your trip itinerary.
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 KidsPlay Museum for some family fun. Additional attractions in the area include Highland Lake and Burr Pond State Park.
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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