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Check availability on Winchester 2 Star Hotels

Tonight
Aug 31 - Sep 1
Tomorrow
Sep 1 - Sep 2
Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14

Compare Winchester 2 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Extended Stay America Suites Hartford Farmington
Deluxe Studio, Multiple Beds, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets

Extended Stay America Suites Hartford Farmington

2.5 star property
8.0 out of 10, Very Good, (987)
"Had a great time, clean, quiet, staff respectful."
$104 nightly
The price is $120
Sep 7 - Sep 8
Total with taxes and fees
Extended Stay America Suites Hartford Farmington
Fairfield Inn & Suites by Marriott Plainville
Lobby

Fairfield Inn & Suites by Marriott Plainville

2.5 star property
8.6 out of 10, Excellent, (882)
"Great stay would and will stay again "
$96 nightly
The price is $110
Sep 14 - Sep 15
Total with taxes and fees
Fairfield Inn & Suites by Marriott Plainville
Hampton Inn & Suites Hartford/Farmington
Exterior

Hampton Inn & Suites Hartford/Farmington

2.5 star property
8.8 out of 10, Excellent, (1003)
"Nice staff and good location"
$155 nightly
The price is $178
Sep 21 - Sep 22
Total with taxes and fees
Hampton Inn & Suites Hartford/Farmington
Days Inn by Wyndham Torrington
Exterior

Days Inn by Wyndham Torrington

2.0 star property
7.4 out of 10, Good, (1002)
"Very comfortable for a weeks' stay. Good location "
$82 nightly
The price is $94
Sep 7 - Sep 8
Total with taxes and fees
Days Inn by Wyndham Torrington
Americas Best Value Inn Torrington CT
Premium bedding, down comforters, Select Comfort beds, in-room safe

Americas Best Value Inn Torrington CT

2.5 star property
5.6 out of 10, (749)
"Tina, front desk rep, was lovely & helpful. She was the best part of our overnight stay."
$93 nightly
The price is $108
Sep 7 - Sep 8
Total with taxes and fees
Americas Best Value Inn Torrington CT
Hitching Post Country Motel
Front of property

Hitching Post Country Motel

2.5 star property
6.6 out of 10, (62)
"It was all I needed Hosts were very gracious. "
$130 nightly
The price is $150
Sep 2 - Sep 3
Total with taxes and fees
Hitching Post Country Motel
PLYMOUTH MOTOR LODGE
Interior

PLYMOUTH MOTOR LODGE

2.5 star property
7.6 out of 10, Good, (158)
"Good stay for an overnight stop"
$78 nightly
The price is $90
Sep 3 - Sep 4
Total with taxes and fees
PLYMOUTH MOTOR LODGE
Wilder House Berkshires
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (29)
"Beautiful and very comfortable house. Our hosts were always friendly and accessible, breakfast was delicious!"
$190 nightly
The price is $212
Sep 28 - Sep 29
Total with taxes and fees
Wilder House Berkshires
The Millerton Inn
Exterior

The Millerton Inn

2.0 star property
8.0 out of 10, Very Good, (8)
"Beautiful property, only stayed one night for business but it was very nice. Great burger at the restaurant downstairs! Possibly one of the best burgers I’ve ever had!"
The Millerton Inn
Sunny, vintage farmhouse in the center of quintessential New England farm town.
Exterior

Sunny, vintage farmhouse in the center of quintessential New England farm town.

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great property, very cozy and alot of history in the house. Host goes above and beyond to make sure everything is ready for your stay. Communication is out of this world. Would absolutely stay again. "
Sunny, vintage farmhouse in the center of quintessential New England farm town.
Steele Brook Manor Tranquil get away nestled in Litchfield County.
Interior

Steele Brook Manor Tranquil get away nestled in Litchfield County.

2.0 star property
9.6 out of 10, Exceptional, (4)
"This apartment in an older home met all of our needs. It was well-equipped and well-furnished, neat and clean, quiet with ample parking. "
Steele Brook Manor Tranquil get away nestled in Litchfield County.
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
9.0 out of 10, Wonderful, (4)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House
Lake Congamond Cozy Stylish Comfortable House
Sun loungers, beach towels

Lake Congamond Cozy Stylish Comfortable House

2.0 star property
9.6 out of 10, Exceptional, (7)
"This cozy cottage was perfect. It was definitely a great lication and close to a lot of stores. The beds were really comfortable too. Thesellerr was super helpfula sn"
Lake Congamond Cozy Stylish Comfortable House
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Terrace/patio

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

2.0 star property
10.0 out of 10, Exceptional, (6)
"This was a perfect base camp for my family's long weekend trip to hit a few towns and ski hills (Butternut, Catamount) in the region. The house was perfect for our family of 5 and was clean, well appointed and was a great mix of modern/updated and classic charm. The location was super convenient (10-min to town and 5-min to ski) yet it was nice to be in our own house surrounded by woods. I would really like to come back in the summer as it is also very close to lake access, appalachian trail,...
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Elm Motel
Reception

Elm Motel

2.0 star property
7.2 out of 10, Good, (123)
"Very clean, lacking bathroom and bathroom storage. Good price."
$89 nightly
The price is $99
Sep 2 - Sep 3
Total with taxes and fees
Elm Motel
Cozy 4 Bedroom West Hartford House
Exterior

Cozy 4 Bedroom West Hartford House

2.0 star property
8.8 out of 10, Excellent, (6)
"The property was very roomy and comfortable for our family of 11. My only concerns were livingroom couches look like they need a good cleaning and home was a bit dated in areas. Parking and Amenities such as water, shampoo, body wash were great. "
Cozy 4 Bedroom West Hartford House
Race Brook Lodge
Exterior

Race Brook Lodge

2.0 star property
8.4 out of 10, Very Good, (31)
" Wonderful property, food, relaxation, and friendly staff. "
Race Brook Lodge
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
Property grounds

Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

2.0 star property
10.0 out of 10, Exceptional, (11)
"Marko was a fantastic host! So responsive and friendly! The property was beyond words. Every piece of decor had a story! We loved it SO much that my husband and our friends will be returning next year! We got there to find that Marko left us a lovely note and a bottle of wine! Gave us great suggestions on things to do and we wanted for NOTHING…Everything we needed was both available indoors and outdoors! The babbling brook with the yoga area was so zen! We absolutely enjoyed ourselves and...
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
10.0 out of 10, Exceptional, (2)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
$555 nightly
The price is $629
Sep 10 - Sep 11
Total with taxes and fees
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Interior

Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice apartment. Beautiful grounds and gardens. We enjoyed ourselves. It was a very comfy place to return to as we enjoyed Jacob's Pillow and our other explorations around the Berkshires. "
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
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Explore similar 3-star hotels

Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Winchester.
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

1 Bradley International Airport, Windsor Locks, CT
$259 nightly
The price is $298 total per night from Sep 5 to Sep 6
$298 total
Sep 5 - Sep 6
Total with taxes and fees
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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.

Top Winchester Hotel Reviews

Find out more about Winchester

Find out more about Winchester

Winchester Motel Guide

Planning a getaway with only a few bucks to spare? Expedia can help! With the inexpensive rates at the top motels in Winchester, Winsted you can put together the vacation of your dreams without spending every penny of your yearly travel budget.

These smaller places are ideal if you need a home base that lets you easily explore the local sights; many of the best motels in Winchester are located near major freeways and public transportation. Plus, when you book a cheap deal on a motel in Winchester, you’ll find quiet rooms, complimentary toiletries, and comfortable sleeping areas, so you can unwind after a long day.

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