Hotels in Winchester from P6,687 for 2026 - Fully Refundable Options

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Our top choices for Winchester hotels

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

A cozy living room with floral wallpaper, a sofa, a coffee table, and two lamps.

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

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

1. Blackberry River Inn

Norfolk

Donna

P11,924

P13,713 total

includes taxes & fees

Oct 14 - Oct 15

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

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

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

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

2. Days Inn by Wyndham Torrington

Torrington

Alyson

P5,815

P6,687 total

includes taxes & fees

Nov 8 - Nov 9

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.

3. Manor House Inn

Norfolk

Kevin

P21,925

P24,336 total

includes taxes & fees

Oct 19 - Oct 20

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

A motel with a covered entrance, a parking lot, and a building with a sign that reads "LARRY'S".

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

4. Americas Best Value Inn Torrington CT

Torrington

Carol

P8,535

P9,815 total

includes taxes & fees

Oct 16 - Oct 17

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

5. The Litchfield Inn

Litchfield

Jacqueline

P19,588

P22,527 total

includes taxes & fees

Nov 2 - Nov 3

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

A stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.

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

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

6. Residence Inn by Marriott Hartford Avon

Avon

Laura

P9,015

P10,368 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

7. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

P6,590

P7,578 total

includes taxes & fees

Oct 20 - Oct 21

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.

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

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

8. The Abner Hotel

Litchfield Historic District

Roseann

P14,325

P16,474 total

includes taxes & fees

Nov 11 - Nov 12

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 brick building with a covered patio, a fountain, and a staircase leading to a second floor.

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

9. Simsbury Inn

Simsbury Center

SueEllen and Ian

P18,137

P22,229 total

includes taxes & fees

Oct 19 - Oct 20

A hotel with a prominent sign, a covered entrance, and a landscaped driveway.

A hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.

A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.

An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.

10. Hampton Inn & Suites Hartford/Farmington

Farmington

Jessica

P9,131

P10,501 total

includes taxes & fees

Oct 30 - Oct 31

A bedroom with a large bed, a chair, and a window with curtains.

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

A covered porch with a dining area, a sofa, and decorative wall art.

11. The White Hart

Salisbury

William

P56,671

P65,172 total

includes taxes & fees

Oct 24 - Oct 25

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

12. Simsbury 1820 House

Simsbury Center

Kimberly

P11,005

P13,740 total

includes taxes & fees

Nov 4 - Nov 5

A hotel with multiple buildings, a parking lot, and a well-maintained lawn.

A hotel room with a bed, a sofa, a desk, a chair, a TV, and a lamp.

A swimming pool with lounge chairs and a red door.

A modern lobby with a yellow sofa, marble table, and two armchairs.

13. Homewood Suites by Hilton Hartford-Farmington

Farmington

EDWARD

P10,616

P12,208 total

includes taxes & fees

Oct 25 - Oct 26

A large outdoor chessboard set up on a grassy area with a pavilion in the background.

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 reception desk.

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

14. Avon Old Farms Hotel

Avon

William

P11,861

P15,012 total

includes taxes & fees

Oct 14 - Oct 15

A modern hotel lobby with seating arrangements, a central dining table, and a kitchenette area.

A hotel room with two beds, a desk, a chair, a TV, a lamp, a small table with bottles, and a framed picture on the wall.

A reception desk with a wooden backdrop and a large, detailed drawing of a ship.

A hotel kitchenette with a microwave, coffee maker, and a sink.

15. Sheraton Hartford Hotel at Bradley Airport

Windsor Locks

John

P15,966

P18,361 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

16. DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

Carroll

P10,223

P11,757 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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.

17. The Old Inn On The Green

Great Barrington

Catherine

P18,200

P21,962 total

includes taxes & fees

Nov 8 - Nov 9

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

A modern bar area with a counter, bar stools, and a variety of bottles.

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

A tented area with lush greenery and a dining setup.

18. Interlaken Inn & Resort

Lakeville

Stacie

P16,340

P18,791 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

19. The Farmington Inn & Suites

Farmington

Brian

P8,724

P11,115 total

includes taxes & fees

Nov 8 - Nov 9

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 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.

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.

20. Sunny Peace Homestay

Harwinton

Dean

P8,190

P13,027 total

includes taxes & fees

Oct 14 - Oct 15

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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.

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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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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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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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Rowley Fields

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

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Ledgebrook Plaza

You can enjoy retail therapy at Ledgebrook Plaza during your stay in Winchester.

See properties

Top Winchester Hotel Reviews

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent

"The front desk staff was so amazing. They helped us from the moment of our arrival. Will definitely stay there again !!!"

The Farmington Inn & Suites

8/10 Good

"The room was nice though a few stains on the bathroom ceiling and the floor creaked a lot when the people above walked around but overall it was very nice. I was looking forward to waffles for breakfast but they were out of batter and I didn’t have a lot of time to wait and find someone to refill it. I enjoyed my stay and would stay again though I thought it was a bit pricey."

The Litchfield Inn

10/10 Excellent

"Quite simply excellent. This was an overnight stop on our Fall Foliage tour of New England this year. It is not often that I can't think of something that could be improved but nothing comes to mind about this place."

Delamar West Hartford

10/10 Excellent

"Best value in Greater Hartford - 1st class accomodations - fair price"

The Abner Hotel

10/10 Excellent

"The hotel is an old courthouse with an incredible charm. It is spacious and comfortable. It has the feel of old time charm yet it is brand new. The staff could not have been more helpful and pleasant. We really enjoyed our stay and will certainly go back!"

Days Inn by Wyndham Torrington

8/10 Good

"Dated building and area , no elevator , towels not replaced daily , no exter to in room , min. On roll provided , yogurt, fruit cup , and carbs for breakfast , no juice"

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent

"Location, Location, Location... perfect for departing from BDL. Restaurant was very good and bar area was clean and had a wide open area for seating."

Simsbury Inn

8/10 Good

"The rooms are nice and very comfortable. The ground are beautiful. The breakfast buffet was often cold and the food not great."

Simsbury 1820 House

10/10 Excellent

"Lovely comfortable place!!"

More cheap stays in Winchester

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

P5,815

P6,687 total

Nov 8 - Nov 9

includes taxes & fees

7.4/10 Good! (1,003 reviews)

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT

P7,638

P8,784 total

Nov 1 - Nov 2

includes taxes & fees

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT

P8,159

P9,382 total

Oct 18 - Oct 19

includes taxes & fees

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

P8,535

P9,815 total

Oct 16 - Oct 17

includes taxes & fees

5.6/10 (825 reviews)

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT

P9,131

P10,501 total

Oct 30 - Oct 31

includes taxes & fees

The Millerton Inn

53 Main St Millerton NY

P15,759

P17,827 total

Oct 14 - Oct 15

includes taxes & fees

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.

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.

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.

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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. Blackberry River Inn

2. Days Inn by Wyndham Torrington

3. Manor House Inn

4. Americas Best Value Inn Torrington CT

5. The Litchfield Inn

6. Residence Inn by Marriott Hartford Avon

7. Locust Tree Bed and Breakfast LLC

8. The Abner Hotel

9. Simsbury Inn

10. Hampton Inn & Suites Hartford/Farmington

11. The White Hart

12. Simsbury 1820 House

13. Homewood Suites by Hilton Hartford-Farmington

14. Avon Old Farms Hotel

15. Sheraton Hartford Hotel at Bradley Airport

16. DoubleTree by Hilton Hotel Bristol, Connecticut

17. The Old Inn On The Green

18. Interlaken Inn & Resort

19. The Farmington Inn & Suites

20. Sunny Peace Homestay

Stay near popular Winchester attractions

Highland Lake

The Marina at Highland Lake

Northwestern Connecticut Community College

Northwestern Connecticut Community College Library

Winchester Historical Society

American Mural Project

Rowley Fields

Ledgebrook Plaza

Top Winchester Hotel Reviews

DoubleTree by Hilton Hotel Bristol, Connecticut

The Farmington Inn & Suites

The Litchfield Inn

Delamar West Hartford

The Abner Hotel

Days Inn by Wyndham Torrington

Sheraton Hartford Hotel at Bradley Airport

Simsbury Inn

Simsbury 1820 House

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

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