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Check availability on Winchester Cheap Hotels

Our top choices for Winchester cheap hotels

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, (415 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is NT$3,352
NT$3,854 total
includes taxes & fees
Mar 19 - Mar 20
Locust Tree Bed and Breakfast LLC
Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (104 reviews)
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
The price is NT$4,469
NT$4,960 total
includes taxes & fees
Mar 19 - Mar 20
Truman Gillet House Bed & Breakfast
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (201 reviews)
"Great place good people decent breakfast great room service "
United States
JULES
The price is NT$4,150
NT$4,772 total
includes taxes & fees
Apr 2 - Apr 3
Home2 Suites by Hilton Bristol
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is NT$5,137
NT$5,738 total
includes taxes & fees
Mar 19 - Mar 20
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, (1,004 reviews)
"Staff was very attentive to my needs. I required support on two occasions during the length of my stay and they took care of the problem immediately. "
United States
Michele
The price is NT$2,957
NT$3,401 total
includes taxes & fees
Apr 7 - Apr 8
Days Inn by Wyndham Torrington
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very Good, (18 reviews)
"Perfect "
United States
Zhigang
The price is NT$5,145
NT$5,820 total
includes taxes & fees
Mar 20 - Mar 21
The Millerton Inn
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (171 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is NT$4,970
NT$5,715 total
includes taxes & fees
Mar 19 - Mar 20
Blackberry River Inn
Exterior

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1,004 reviews)
"Stay was great! "
United States
Teresa
The price is NT$6,767
NT$7,782 total
includes taxes & fees
Apr 4 - Apr 5
Sheraton Hartford Hotel at Bradley Airport
Interior

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.8 out of 10, Good, (183 reviews)
"Nice amount of space"
United States
Amanda
The price is NT$2,554
NT$2,937 total
includes taxes & fees
Mar 19 - Mar 20
PLYMOUTH MOTOR LODGE
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (54 reviews)
"My stay was flawless. From staff to the clean room and comfortable bedding all made for an amazing experience."
United States
Francis
The price is NT$8,459
NT$9,728 total
includes taxes & fees
Mar 22 - Mar 23
The Abner Hotel
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

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

8/10 Good
"Clean comfortable room though it’s a little dated. "
Lester 3-night trip
Posted 2 days ago
Extended Stay America Suites Hartford Farmington

Frequently asked questions

What is Winchester like for travelers on a budget?
Check out discount places to stay in Winchester on Expedia.com and plan a trip that sticks within your budget. You can scroll through a variety of accommodations with Member Prices to score great deals. With our site's helpful page filters, you can limit results by your price range, or by top amenities like free parking and free WiFi. If you're hoping for reasonable options around local sights, such as Highland Lake or Platt Hill State Park, try out the location filters to narrow down your search. As you browse, use the heart button to save your favorites so that you can find them later when you're ready to decide. Interested in a flight or a rental car too? Choose from the travel packages offered under Bundle and Save and discover big savings when you arrange your transportation at the same time.
When is the best time for a budget trip to Winchester?
Weather will likely play an important role when you plan your trip to Winchester, and keep in mind that cheaper options are usually available when the weather isn't as good. 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 is there to see and do in Winchester?
You won't need to spend a lot to find things to see and do in Winchester. You can budget for the local attractions that interest you most, and then make time for sights and activities that are easy on the wallet. Enjoy the local natural beauty at Highland Lake and Walker Field, or check out the area's cultural spots like Winchester Historical Society.
How can I get to Winchester and get around on a budget?
Scoping out the transportation options in Winchester is a smart way to keep your trip affordable. The most convenient airport is 21.9 mi (35.2 km) away from the center in Bradley Intl. Airport (BDL). However, if that doesn't suit your budget, you can book a flight to Westfield, MA (BAF-Barnes Municipal), located 25.8 mi (41.5 km) away. Winchester might not have many public transportation choices so a rental car could be a reasonable alternative to see the area.

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