Top 10 Hotels in Winchester, CT from AED 355 - Competitive Prices

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Our top choices for Winchester hotels

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

A dining table with a plate of food and two wine glasses, set in a room with leather furniture and a fireplace in the background.

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

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

1. Manor House Inn

Norfolk

Kevin

AED 1,115

AED 1,238 total

includes taxes & fees

21 Oct - 22 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

AED 551

AED 634 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

3. Americas Best Value Inn Torrington CT

Torrington

Carol

AED 499

AED 574 total

includes taxes & fees

9 Oct - 10 Oct

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

A Days Inn sign with a sunburst design, surrounded by trees.

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.

4. Days Inn by Wyndham Torrington

Torrington

Alyson

AED 309

AED 355 total

includes taxes & fees

25 Oct - 26 Oct

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

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

A spacious foyer with a wooden staircase, a reception desk, and a seating area.

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

5. The Abner Hotel

Litchfield Historic District

JANET

AED 629

AED 723 total

includes taxes & fees

1 Nov - 2 Nov

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.

6. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

AED 386

AED 444 total

includes taxes & fees

11 Oct - 12 Oct

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 long wooden table with potted plants and candle holders in a modern interior setting.

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

7. The Litchfield Inn

Litchfield

Wei

AED 1,140

AED 1,311 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

8. Gedney Farm

Great Barrington

Terri

AED 696

AED 764 total

includes taxes & fees

3 Nov - 4 Nov

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

A sign for the Simsbury House, indicating it is a historic building from 1820.

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

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

9. Simsbury 1820 House

Simsbury Center

Kimberly

AED 643

AED 803 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

10. Residence Inn by Marriott Hartford Avon

Avon

RAE

AED 528

AED 607 total

includes taxes & fees

1 Nov - 2 Nov

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

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

11. Home2 Suites by Hilton Bristol

Bristol

Gabriela

AED 479

AED 551 total

includes taxes & fees

1 Nov - 2 Nov

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

A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

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

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

12. The Old Inn On The Green

Great Barrington

Catherine

AED 1,065

AED 1,285 total

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

A dining room with a table set for four, surrounded by wooden chairs. A chandelier hangs above the table, and a vase with flowers is on the table.

13. Truman Gillet House Bed & Breakfast

Granby

Melanie

AED 514

AED 571 total

includes taxes & fees

11 Oct - 12 Oct

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 reception desk.

A spacious indoor dining area with high ceilings, large windows, and a brick wall.

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

14. Avon Old Farms Hotel

Avon

William

AED 708

AED 894 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

A four-poster bed in a hotel room with a blue carpet, a desk with a lamp, a chair, and a bedside table with a lamp.

15. The Farmington Inn & Suites

Farmington

Brian

AED 444

AED 574 total

includes taxes & fees

1 Nov - 2 Nov

A wooden deck with a swing chair and a bench overlooking a lake.

A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

A modern hotel room with a bed, sofa, leather chair, and a small table.

A tented area with lush greenery and a dining setup.

16. Interlaken Inn & Resort

Lakeville

Stacie

AED 790

AED 909 total

includes taxes & fees

8 Nov - 9 Nov

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

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

A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.

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

17. DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

DARRON

AED 590

AED 679 total

includes taxes & fees

18 Oct - 19 Oct

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

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

A spacious room with a high ceiling, a ceiling fan, a large window with a view of greenery, a white sofa, a black leather chair, and a wooden table with a computer setup.

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.

18. Sunny Peace Homestay

Harwinton

Dean

AED 479

AED 762 total

includes taxes & fees

12 Oct - 13 Oct

A stone fountain with water spouting from the top, surrounded by greenery and a brick building with windows in the background.

A person in a blue swimsuit relaxing in a hot tub with a pool in the background.

A spacious, well-lit event space with a glass ceiling, white tables, and a chandelier.

A large, multi-story building surrounded by dense forest, with a parking lot and a small green structure nearby.

19. Simsbury Inn

Simsbury Center

Kristen

AED 1,062

AED 1,301 total

includes taxes & fees

12 Oct - 13 Oct

A dining area with wooden tables and chairs, large windows with white frames, and wall-mounted light fixtures.

A two-story building with a sign for Cornwall Inn, featuring a front porch and a mailbox.

A hotel room with a large bed, two bedside lamps, a chair, a small table, and a rug.

A covered patio with a wooden table and chairs, a sofa, and a ceiling fan.

20. Cornwall Inn and Lodge

Cornwall Bridge

Richard T

AED 777

AED 894 total

includes taxes & fees

1 Nov - 2 Nov

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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.

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Northwestern Connecticut Community College

Walk around the campus at Northwestern Connecticut Community College as part of your travels around Winchester.

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Winchester Historical Society

8.0/10 (1 review)

You can spend an afternoon exploring the galleries in Winchester Historical Society during your trip to Winchester. Take in the live music in this relaxing area.

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American Mural Project

You can spend time studying the exhibits at American Mural Project in Winchester.

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Northwestern Connecticut Community College Library

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

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Platt Hill State Park

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

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Rowley Fields

Explore the great outdoors at Rowley Fields, a lovely green space in Winchester.

See properties

Top Winchester Hotel Reviews

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"

Home2 Suites by Hilton Bristol

10/10 Excellent

"Property was very clean and well maintained. The first thing that caught my attention was how good it smelled almost reminds you of a newer property. Staff was very friendly amenities were great very pleasant day."

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

AED 309

AED 355 total

25 Oct - 26 Oct

includes taxes & fees

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT

AED 447

AED 514 total

25 Oct - 26 Oct

includes taxes & fees

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT

AED 477

AED 549 total

11 Oct - 12 Oct

includes taxes & fees

6.6/10 (112 reviews)

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

AED 499

AED 574 total

9 Oct - 10 Oct

includes taxes & fees

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT

AED 609

AED 700 total

12 Oct - 13 Oct

includes taxes & fees

The Millerton Inn

53 Main St Millerton NY

AED 922

AED 1,043 total

13 Oct - 14 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 traveler data. Other good choices for your visit to the area are Delamar West Hartford and Extended Stay America Suites Hartford Farmington. See all available top hotels, or vacation rentals in Winchester.

What's the top vacation rental in Winchester?

Waterfront House & Guest House Available in Winchester, CT!: This Winchester vacation home rental 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! You'll find that most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

To access more information about picking new dates or cancelling your trip to Winchester, head over to our customer service page.

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 onsite pool. View all hotels with pools in Winchester.

What is staying in Winchester like?

Visitors to Winchester are sure to find plenty to explore and enjoy. In Winchester, there are 21 hotels and other accommodations to choose from. Find out more about Winchester.

What should I do while I'm visiting Winchester?

Favorite 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 agenda are Winchester Historical Society and American Museum of Tort Law. Check out what more to see and do in Expedia's Winchester guide.

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.

Find hotels in Winchester, CT from AED 355

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. Manor House Inn

2. Blackberry River Inn

3. Americas Best Value Inn Torrington CT

4. Days Inn by Wyndham Torrington

5. The Abner Hotel

6. Locust Tree Bed and Breakfast LLC

7. The Litchfield Inn

8. Gedney Farm

9. Simsbury 1820 House

10. Residence Inn by Marriott Hartford Avon

11. Home2 Suites by Hilton Bristol

12. The Old Inn On The Green

13. Truman Gillet House Bed & Breakfast

14. Avon Old Farms Hotel

15. The Farmington Inn & Suites

16. Interlaken Inn & Resort

17. DoubleTree by Hilton Hotel Bristol, Connecticut

18. Sunny Peace Homestay

19. Simsbury Inn

20. Cornwall Inn and Lodge

Stay near popular Winchester attractions

Highland Lake

The Marina at Highland Lake

Northwestern Connecticut Community College

Winchester Historical Society

American Mural Project

Northwestern Connecticut Community College Library

Platt Hill State Park

Rowley Fields

Top Winchester Hotel Reviews

Simsbury 1820 House

Delamar West Hartford

The Litchfield Inn

Home2 Suites by Hilton Bristol

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

Go further with the Expedia app