Winchester Hotels from €88 - Fully Refundable Options

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Winchester

Apartment

Waterpark

Hot tub

Pet friendly

Pool

Condo

Family friendly

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Winchester hotels

A hotel room with a bed, white pillows, a bedside table with a phone, and a wall-mounted TV displaying a scenic sunset.

A breakfast bar with a coffee machine, toaster, and various food items.

A Days Inn building with a blue awning, a lobby entrance, and a well-maintained lawn with various plants.

A bathroom with a bathtub, toilet, and granite countertop sink.

1. Days Inn by Wyndham Torrington

Torrington

Alyson

€88

includes taxes & fees

18 Oct - 19 Oct

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

A grand hallway with a chandelier, a staircase, and a table with flowers.

A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

A room with a fireplace, two striped armchairs, and a floral drape.

2. Blackberry River Inn

Norfolk

Donna

€195

includes taxes & fees

13 Oct - 14 Oct

A hotel room with a large bed, bedside lamps, a desk with a chair, a mirror, and a coat rack.

A gym with various exercise equipment, a mirror, and a blue wall.

A spacious living area with a brown leather sofa, a glass coffee table, a wooden entertainment unit with a flat-screen TV, and a large window providing a view of the outdoors.

3. Americas Best Value Inn Torrington CT

Torrington

€139

includes taxes & fees

12 Oct - 13 Oct

A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

A two-story building with a flat roof, solar panels, and a small patio area.

A bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

4. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

€108

includes taxes & fees

12 Oct - 13 Oct

A patio with a round metal table, a glass of white wine, and a red umbrella.

A grand staircase with a wooden railing, leading to a room with large windows and a patterned ceiling.

A large, two-story house with a steeply pitched roof, stone foundation, and a well-maintained garden with various shrubs and a fountain.

A cozy room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

5. Manor House Inn

Norfolk

Kevin

€345

includes taxes & fees

19 Oct - 20 Oct

A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

A modern living room with a sofa, ottoman, and green armchair, a coffee table with a vase of flowers, and a wooden cabinet with decorative items.

A modern living room with a sofa, ottoman, and green chairs, a coffee table with flowers, and a side table with a lamp and decorative items.

A house with a garden featuring purple flowers and a stone wall.

6. Sunny Peace Homestay

Harwinton

Dean

€185

includes taxes & fees

14 Oct - 15 Oct

A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.

An outdoor patio area with wooden flooring, green metal chairs, and tables under umbrellas.

An outdoor seating area with green chairs and tables, a bar with shelves of bottles, and a view of trees in the background.

A hotel room with a bed, a sofa, a small table, a floor lamp, and two windows with curtains.

7. The Abner Hotel

Litchfield Historic District

JANET

€234

includes taxes & fees

1 Nov - 2 Nov

A house with a porch, American flags, and a pathway leading to a bench.

A living room with a fireplace, a wooden cabinet, a plaid sofa, and a patterned rug.

A wooden desk with a notebook, two mugs, a framed sign, a telephone, and a decorative bowl.

A four-poster bed with floral bedding, two bedside lamps, and a wooden floor.

8. Truman Gillet House Bed & Breakfast

Granby

Melanie

€139

includes taxes & fees

11 Oct - 12 Oct

A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.

A well-lit room with a fireplace, two armchairs, a sofa, and a coffee table.

A spacious lobby with a patterned rug, a potted plant, and a television.

A well-lit living room with a patterned sofa, armchairs, a television, and a patterned carpet.

9. The Farmington Inn & Suites

Farmington

Brian

€158

includes taxes & fees

1 Nov - 2 Nov

A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.

A wooden sign with "GEDNEY FARM" written on it, surrounded by lush greenery and purple flowers.

A rustic barn-style venue with round tables and chairs, string lights, and a central bar area.

An outdoor patio with wooden tables and chairs, surrounded by greenery.

10. Gedney Farm

Great Barrington

Terri

€197

includes taxes & fees

2 Nov - 3 Nov

A large, historic building with a covered porch and outdoor seating area.

A grand foyer with a patterned carpet, a wooden staircase, a chandelier, a mounted deer head, and a large clock.

A large, historic house with multiple chimneys, a covered porch, and lush greenery.

A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.

11. Simsbury 1820 House

Simsbury Center

Kimberly

€195

includes taxes & fees

4 Nov - 5 Nov

A conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.

A spacious lobby with a grand staircase, multiple seating areas, and a central decorative table.

A spacious lobby with a grand staircase, multiple seating areas, and a reception desk.

A large conference room with multiple round tables, beige chairs, chandeliers, and a wooden floor.

12. Avon Old Farms Hotel

Avon

William

€217

includes taxes & fees

26 Oct - 27 Oct

An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.

A large indoor swimming pool with multiple seating areas and large windows.

A modern hotel building with multiple floors and a prominent "HOME 2 SUITES BY HILTON" sign.

A modern lounge with a pool table, comfortable seating, and a large window offering a view of the outdoors.

13. Home2 Suites by Hilton Bristol

Bristol

Gabriela

€134

includes taxes & fees

1 Nov - 2 Nov

A lobby with a chandelier, a reception desk, and a sign indicating an exit.

A spacious living room with a fireplace, a dining area, and a sofa.

A rustic bedroom with a large bed, wooden headboard, and a wooden floor. There is a chair and a small table with a lamp.

A white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.

14. The Litchfield Inn

Litchfield

Wei

€312

includes taxes & fees

9 Nov - 10 Nov

An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

A spacious lobby with large windows, a central plant, and multiple hanging lights.

A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.

A modern lobby with a reception desk, seating area, and a large decorative light fixture.

15. DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

DARRON

€161

includes taxes & fees

18 Oct - 19 Oct

A dining area with round tables set for two, a fireplace, and a mural on the wall.

A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

A white two-story house with a front door, windows, and a chimney.

A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

16. The Old Inn On The Green

Great Barrington

Catherine

€312

includes taxes & fees

1 Nov - 2 Nov

A hotel room with two beds, a nightstand with a lamp, and a wall-mounted phone.

A motel with a sign reading "Plymouth Motor Lodge".

A bathroom with a shower, toilet, and towel rack.

A hotel room with a kitchenette, a desk, a chair, a mirror, and a door.

17. PLYMOUTH MOTOR LODGE

Terryville

SEMORA

€91

includes taxes & fees

13 Oct - 14 Oct

An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.

A hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.

A swimming pool with lounge chairs and a covered seating area, surrounded by multi-story buildings with visible windows and a brick facade.

A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.

18. Residence Inn by Marriott Hartford Avon

Avon

€147

includes taxes & fees

1 Nov - 2 Nov

A lobby with a blue sofa, a small round table, and a fireplace.

A hotel reception area with a wooden reception desk, a minibar, and a wall-mounted decorative panel.

A hotel room with a sofa, two small tables, a TV, a desk, and a mirror.

An indoor swimming pool with a 'No Diving' sign, a glass enclosure, and a tiled wall with a 'No Diving' sign.

19. Fairfield Inn & Suites by Marriott Plainville

Plainville

javier adrian

€125

includes taxes & fees

5 Nov - 6 Nov

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

20. Wilder House Berkshires

Sheffield

Mark

€192

includes taxes & fees

29 Oct - 30 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Winchester attractions

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.

See properties

The Marina at Highland Lake

Explore the waterfront in Winchester with a trip to The Marina at Highland Lake.

See properties

Northwestern Connecticut Community College

Explore the campus of Northwestern Connecticut Community College during your stay in Winchester.

See properties

Winchester Historical Society

8.0/10 (1 review)

You can spend an afternoon studying the exhibits at Winchester Historical Society in Winchester. Take in the live music in this relaxing area.

See properties

Northwestern Connecticut Community College Library

After visiting Northwestern Connecticut Community College Library, make a plan to see the other sights and activities in Winchester.

See properties

Platt Hill State Park

You can take time to visit Platt Hill State Park during your travels to Winchester.

See properties

American Mural Project

You can spend time browsing the exhibits at American Mural Project during your trip to Winchester.

See properties

Tatro Pond

You can take time to visit Tatro Pond during your travels to Winchester.

See properties

Top Winchester Hotel Reviews

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent

"The motel was clean and the room we stayed in was clean and smelled good. The staff was awsome . I would recommend the Double Tree to anyone."

Home2 Suites by Hilton Bristol

10/10 Excellent

"Great place. Room was perfect for a night getaway"

Sheraton Hartford Hotel at Bradley Airport

8/10 Good

"Convience"

Simsbury 1820 House

10/10 Excellent

"Lovely comfortable place!!"

Delamar West Hartford

10/10 Excellent

"The staff was amazing. Super helpful and kind. The room was one of the most beautiful and elegant places we’ve stayed at and the hotel amenities, and restaurant was just something I’ll never forget. Thank you for this experience!"

The Litchfield Inn

10/10 Excellent

"The staff was fantastic. Friendly and Informative. Property was very clean. It was nice having the gym and the breakfast"

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent

"Everything was perfect—the room, the service, the restaurant, the spa; everything was perfect. An unforgettable experience."

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

10/10 Excellent

"Pet friendly beautiful clean house on lake. Host is very easy to work with."

More cheap stays in Winchester

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

€88

18 Oct - 19 Oct

includes taxes & fees

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT

€125

1 Nov - 2 Nov

includes taxes & fees

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT

€133

18 Oct - 19 Oct

includes taxes & fees

6.6/10 (112 reviews)

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

€139

12 Oct - 13 Oct

includes taxes & fees

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT

€162

1 Nov - 2 Nov

includes taxes & fees

9/10 Wonderful! (1,001 reviews)

The Millerton Inn

53 Main St Millerton NY

€253

21 Oct - 22 Oct

includes taxes & fees

8.4/10 Very good! (46 reviews)

Frequently asked questions

What's the best place for a stay in Winchester?

The Farmington Inn & Suites, located 20.6 mi (33.1 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Two other choices for your stay in the area are Delamar West Hartford and Extended Stay America Suites Hartford Farmington. See all available top hotels, or vacation rentals in Winchester.

What are some of the best holiday rentals that Winchester has to offer?

Waterfront House & Guest House Available in Winchester, CT!: This highly rated holiday home rental in Winchester is located on a lake, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. See all vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, most hotel bookings are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What are some hotels with pools in Winchester?

Homewood Suites by Hilton Hartford-Farmington: Offers a snack bar/deli, an indoor pool and buffet. Mayflower Inn & Spa, Auberge Collection and Avon Old Farms Hotel are two additional hotels with an on-site pool. View all hotels with pools in Winchester.

What is staying in Winchester like?

Visitors to Winchester will definitely find plenty to explore and enjoy. In Winchester, there are 21 hotels and other accommodation options to choose from. Find out more about Winchester.

What should I see while I'm in Winchester?

Favourite places to visit include Highland Lake, The Marina at Highland Lake and Burr Pond State Park. A couple of additional sights to add to your itinerary are Winchester Historical Society and American Museum of Tort Law. Take a look at what more there is to see and do in Expedia's Winchester guide.

What's the seasonal weather in Winchester?

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.

Explore a world of travel with Expedia

Connecticut Holiday Rentals

Winchester Hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. Days Inn by Wyndham Torrington

2. Blackberry River Inn

3. Americas Best Value Inn Torrington CT

4. Locust Tree Bed and Breakfast LLC

5. Manor House Inn

6. Sunny Peace Homestay

7. The Abner Hotel

8. Truman Gillet House Bed & Breakfast

9. The Farmington Inn & Suites

10. Gedney Farm

11. Simsbury 1820 House

12. Avon Old Farms Hotel

13. Home2 Suites by Hilton Bristol

14. The Litchfield Inn

15. DoubleTree by Hilton Hotel Bristol, Connecticut

16. The Old Inn On The Green

17. PLYMOUTH MOTOR LODGE

18. Residence Inn by Marriott Hartford Avon

19. Fairfield Inn & Suites by Marriott Plainville

20. Wilder House Berkshires

Stay near popular Winchester attractions

Highland Lake

The Marina at Highland Lake

Northwestern Connecticut Community College

Winchester Historical Society

Northwestern Connecticut Community College Library

Platt Hill State Park

American Mural Project

Tatro Pond

Top Winchester Hotel Reviews

DoubleTree by Hilton Hotel Bristol, Connecticut

Home2 Suites by Hilton Bristol

Sheraton Hartford Hotel at Bradley Airport

Simsbury 1820 House

Delamar West Hartford

The Litchfield Inn

Interlaken Inn & Resort

Mayflower Inn & Spa, Auberge Collection

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

More cheap stays in Winchester

Days Inn by Wyndham Torrington

Extended Stay America Suites Hartford Farmington

Hitching Post Country Motel

Americas Best Value Inn Torrington CT

Hampton Inn & Suites Hartford/Farmington

The Millerton Inn

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app