Winchester Holiday Rentals, Winsted: Private House Rentals

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

A kitchen area with a counter, a microwave, a coffee machine, and a display case with pastries.

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

1. Days Inn by Wyndham Torrington

Torrington

Juan

Rp1.639.349

Rp1.885.251 total

includes taxes & fees

26 Aug - 27 Aug

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.

2. Americas Best Value Inn Torrington CT

Torrington

Carol

Rp2.123.103

Rp2.441.568 total

includes taxes & fees

24 Aug - 25 Aug

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

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

3. Avon Old Farms Hotel

Avon

Andrew

Rp2.700.989

Rp3.492.796 total

includes taxes & fees

25 Aug - 26 Aug

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

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

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.

4. The Farmington Inn & Suites

Farmington

Carol

Rp2.636.406

Rp3.337.088 total

includes taxes & fees

24 Aug - 25 Aug

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

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

5. The Litchfield Inn

Litchfield

Sandra

Rp4.832.038

Rp5.556.844 total

includes taxes & fees

24 Aug - 25 Aug

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.

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

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

6. Hampton Inn & Suites Hartford/Farmington

Farmington

Mary Melissa

Rp2.452.035

Rp2.819.841 total

includes taxes & fees

1 Sept - 2 Sept

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

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

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

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

7. Blackberry River Inn

Norfolk

Cheryl

Rp3.361.860

Rp3.866.139 total

includes taxes & fees

24 Aug - 25 Aug

8. Extended Stay America Suites Hartford Farmington

Farmington

Nigel

Rp1.751.529

Rp2.014.285 total

includes taxes & fees

24 Aug - 25 Aug

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

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.

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

9. Simsbury 1820 House

Simsbury Center

Thomas

Rp2.990.286

Rp3.744.050 total

includes taxes & fees

24 Aug - 25 Aug

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

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

10. Residence Inn by Marriott Hartford Avon

Avon

Laura

Rp2.691.257

Rp3.094.945 total

includes taxes & fees

13 Sept - 14 Sept

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

A modern kitchen with a central island, built-in cabinets, and a coffee station.

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

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

11. Homewood Suites by Hilton Hartford-Farmington

Farmington

John

Rp2.510.071

Rp2.886.582 total

includes taxes & fees

7 Sept - 8 Sept

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.

12. Locust Tree Bed and Breakfast LLC

East Canaan

Regina

Rp1.857.870

Rp2.136.551 total

includes taxes & fees

24 Aug - 25 Aug

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

A tented area with lush greenery and a dining setup.

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

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

13. Interlaken Inn & Resort

Lakeville

Stacie

Rp3.805.979

Rp4.376.875 total

includes taxes & fees

22 Sept - 23 Sept

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 Fairfield Inn & Suites hotel with a large parking lot and snow-covered ground.

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

14. Fairfield Inn & Suites by Marriott Plainville

Plainville

Nicole

Rp2.008.623

Rp2.309.917 total

includes taxes & fees

6 Sept - 7 Sept

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

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

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

A framed painting of a white horse on a wooden dresser, a white fireplace with a black mantle, and two green vases with white flowers on the wall.

15. The White Hart

Salisbury

William

Rp6.075.235

Rp6.986.476 total

includes taxes & fees

24 Aug - 25 Aug

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 wooden counter with a wine bottle, glasses, and a sign.

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

16. Cornwall Inn and Lodge

Cornwall Bridge

Janice

Rp3.744.050

Rp4.305.658 total

includes taxes & fees

24 Aug - 25 Aug

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

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.

17. Simsbury Inn

Simsbury Center

Rachel

Rp4.228.866

Rp5.249.810 total

includes taxes & fees

16 Sept - 17 Sept

A hotel room with two beds, a desk, a chair, a small table, and a view of an airport.

A modern hotel room with a large dining table, multiple chairs, a sofa, a TV, and a view through large windows.

18. Sheraton Hartford Hotel at Bradley Airport

Windsor Locks

Lisa

Rp4.051.926

Rp4.659.715 total

includes taxes & fees

29 Aug - 30 Aug

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

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

19. DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

DARRON

Rp2.597.125

Rp2.986.694 total

includes taxes & fees

30 Aug - 31 Aug

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.

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

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

20. Gedney Farm

Great Barrington

Jane

Rp4.060.773

Rp4.454.668 total

includes taxes & fees

24 Aug - 25 Aug

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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

Platt Hill State Park

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

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Northwestern Connecticut Community College

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

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Rowley Fields

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

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Walker Field

Explore the great outdoors at Walker Field, a lovely green space 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.

See properties

Top Winchester Hotel Reviews

Simsbury 1820 House

10/10 Excellent

"The staff at Simsbury 1820 were the highlight of the stay. They were expecially friendly and very helpful. They had some suggestions of things to do that were interesting and area specific. Understandably but a bit disappointing was the inadquacy of the plumbing. It's a very old building but toilets could be updated."

The Farmington Inn & Suites

10/10 Excellent

"Breakfast until 11am was very helpful"

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent

"We have stayed here many times. We always stay here the day before we fly and then the night that we come home. The rooms are always comfortable and clean . The front desk staff are always very nice. It’s an easy walk across the hallway from the airport itself. We have eaten in the restaurant quite a few times and our food is always excellent. I highly recommend staying here."

Home2 Suites by Hilton Bristol

10/10 Excellent

"Ice machines didn't work"

The Litchfield Inn

10/10 Excellent

"From the first time stepping on the property we felt welcome. The staff was accommodating and invited us to enjoy the amenities while we waited for our room (we were early for check in). We took advantage and walked the property before heading off to explore the area. When we returned, we checked into our dog friendly room (after grabbing a freshly baked chocolate chip cookie). The room was clean and comfortable and our dog enjoyed it as well. The next morning we took advantage of the fitness center and pool and enjoyed a hot breakfast on property (made to order omelets were a hit). Overall I cannot say enough good things about the staff, accommodations and amenities. Highly recommend."

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent

"Beautiful property with lovely pool and spa area. The rooms are beautifully decorated. The staff are all friendly, welcoming, and very helpful. The grounds and gardens are well maintained. The hiking trail is highly recommended. My room in the main house was a bit noisy; the room above mine appeared to be a utility room that was active early in the morning. I could hear footsteps throughout the day. The dinner was overrated, but the breakfast and lunch were delicious."

Days Inn by Wyndham Torrington

10/10 Excellent

"Comfortable bed, clean room, stayed overnight for concert in area. Breakfast consisted of yogurt, cereals, bread/bagel, juice, coffee. No coffee maker in room."

Extended Stay America Suites Hartford Farmington

10/10 Excellent

"Dry friendly staff."

Americas Best Value Inn Torrington CT

10/10 Excellent

"All the staff members I met were cheerful & helpful. I asked for a ground floor room, upon arrival, got a very nice one at no extra charge. I was in the area for a music festival, plan on booking a stay again , next year."

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT

Rp1.574.766

Rp1.810.981 total

24 Aug - 25 Aug

includes taxes & fees

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

Rp1.639.349

Rp1.885.251 total

26 Aug - 27 Aug

includes taxes & fees

7.4/10 Good! (1,004 reviews)

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT

Rp1.751.529

Rp2.014.285 total

24 Aug - 25 Aug

includes taxes & fees

8/10 Very good! (1,004 reviews)

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

Rp2.123.103

Rp2.441.568 total

24 Aug - 25 Aug

includes taxes & fees

5.6/10 (809 reviews)

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT

Rp2.300.220

Rp2.645.253 total

24 Aug - 25 Aug

includes taxes & fees

6.6/10 (108 reviews)

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT

Rp2.452.035

Rp2.819.841 total

1 Sept - 2 Sept

includes taxes & fees

Frequently asked questions

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

Sheraton Hartford Hotel at Bradley Airport, located 21.9 mi (35.2 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 Homewood Suites by Hilton Hartford-Farmington and The Farmington Inn & Suites. 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, 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: Features a snack bar/deli, an indoor pool and buffet. Avon Old Farms Hotel and Mayflower Inn & Spa, Auberge Collection 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 19 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, Burr Pond State Park and The Marina at Highland Lake. A couple of additional sights to add to your itinerary are Platt Hill State Park and Laurel Lanes. 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.

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Book Hotels in Winchester on Expedia.com

Find hotels in Winchester, CT from Rp1.810.981

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. Americas Best Value Inn Torrington CT

3. Avon Old Farms Hotel

4. The Farmington Inn & Suites

5. The Litchfield Inn

6. Hampton Inn & Suites Hartford/Farmington

7. Blackberry River Inn

8. Extended Stay America Suites Hartford Farmington

9. Simsbury 1820 House

10. Residence Inn by Marriott Hartford Avon

11. Homewood Suites by Hilton Hartford-Farmington

12. Locust Tree Bed and Breakfast LLC

13. Interlaken Inn & Resort

14. Fairfield Inn & Suites by Marriott Plainville

15. The White Hart

16. Cornwall Inn and Lodge

17. Simsbury Inn

18. Sheraton Hartford Hotel at Bradley Airport

19. DoubleTree by Hilton Hotel Bristol, Connecticut

20. Gedney Farm

Stay near popular Winchester attractions

Highland Lake

Platt Hill State Park

Northwestern Connecticut Community College

The Marina at Highland Lake

Winchester Historical Society

Rowley Fields

Walker Field

Northwestern Connecticut Community College Library

Top Winchester Hotel Reviews

Simsbury 1820 House

The Farmington Inn & Suites

Sheraton Hartford Hotel at Bradley Airport

Home2 Suites by Hilton Bristol

The Litchfield Inn

Mayflower Inn & Spa, Auberge Collection

Days Inn by Wyndham Torrington

Extended Stay America Suites Hartford Farmington

Americas Best Value Inn Torrington CT

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

Days Inn by Wyndham Torrington

Extended Stay America Suites Hartford Farmington

Americas Best Value Inn Torrington CT

Hitching Post Country Motel

Hampton Inn & Suites Hartford/Farmington

Frequently asked questions

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