Cheap Hotels & Resorts in Winchester from AU$115

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Check availability on Winchester Cheap Hotels

Our top choices for Winchester cheap hotels

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 AU$170
includes taxes & fees
19 Mar - 20 Mar
Locust Tree Bed and Breakfast LLC

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 AU$219
includes taxes & fees
19 Mar - 20 Mar
Truman Gillet House Bed & Breakfast

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 AU$212
includes taxes & fees
2 Apr - 3 Apr
Home2 Suites by Hilton Bristol

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 AU$220
includes taxes & fees
24 Mar - 25 Mar
Wilder House Berkshires

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 AU$151
includes taxes & fees
7 Apr - 8 Apr
Days Inn by Wyndham Torrington

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 AU$254
includes taxes & fees
20 Mar - 21 Mar
The Millerton Inn

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 AU$232
includes taxes & fees
1 Apr - 2 Apr
Blackberry River Inn

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 AU$343
includes taxes & fees
4 Apr - 5 Apr
Sheraton Hartford Hotel at Bradley Airport

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 AU$115
includes taxes & fees
19 Mar - 20 Mar
PLYMOUTH MOTOR LODGE

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 AU$429
includes taxes & fees
22 Mar - 23 Mar
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.

Find out more about Winchester

Discover cheap things to do in Winchester

Winchester, Connecticut, offers a charming escape for budget-conscious travellers eager to explore its natural beauty and quaint atmosphere. Start your adventure at the scenic Lake Winchester, where you can enjoy a leisurely stroll along the shore or even a picnic with the family—perfect for a day of relaxation without spending a dime. Next, visit the historic Winchester Center, where you’ll find a delightful collection of antique shops and local boutiques, perfect for window shopping or finding unique gifts at affordable prices. For outdoor enthusiasts, the nearby Burr Pond State Park offers free hiking trails with stunning views, ideal for a family outing or a peaceful day in nature. Don’t miss out on the local dining scene—head to the family-friendly restaurant, The Greenhouse Café, where you can savour hearty meals without breaking the bank. For a comfortable stay, consider the area around Route 44, where you can find budget-friendly hotels that offer convenience and easy access to these attractions, making it a breeze to explore the best of Winchester while enjoying attentive service that caters to your family's needs.

Top Winchester Hotel Reviews

Frequently asked questions

What is Winchester like for travellers on a budget?
Discover cheap places to stay in Winchester on Expedia.com and plan a getaway that matches your budget. You can browse a wide range of hotels and other accommodation options with Member Prices to find great deals and earn rewards. With our site's handy page filters, you can search by your price range, or by popular amenities like free breakfast and a swimming pool. 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 keep track of your favourites so that you can come back to them when you're ready to book. Interested in a car or a flight too? Take a look at the holiday packages available under Bundle and Save and discover huge discounts by arranging transport 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, but bear 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 temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 15 cm of snowfall.
What is there to see and do in Winchester?
You don't have to spend a fortune to take advantage of things to see and do in Winchester. You can budget for the local attractions that interest you most, and then fill your itinerary with sights that cost little or nothing at all. 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 nearest airport is 21.9 mi (35.2 km) away from the centre in Hartford, CT (BDL-Bradley Intl.). 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 very many public transport choices so renting a car could be a reasonable alternative to see the area.

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