---
title: "Holiday Rentals Winsted from £1,080: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk"
description: "Winsted Holiday Rentals: find great deals on holiday home rentals, villas, apartments, cottages and other holiday homes in Winsted with Expedia"
canonical: "https://www.expedia.co.uk/Winsted-Holiday-Rentals.d3000430645.Travel-Guide-HolidayRentals"
language: en-GB
market: GB
currency: GBP
prices_as_of: 2026-11-14T11:20:42Z
---

Plan your trip

- [Winsted Travel Guide](https://www.expedia.co.uk/Winsted.dx3000430645)
- [Hotels in Winsted](https://www.expedia.co.uk/Winsted-Hotels.d3000430645.Travel-Guide-Hotels)
- [Flights to Winsted](https://www.expedia.co.uk/Cheap-Flights-To-Winsted.d3000430645.Travel-Guide-Flights)
- [Car Hire in Winsted](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Winsted.d3000430645.Car-Hire-Guide)
- [Winsted Holiday Packages](https://www.expedia.co.uk/Winsted.d3000430645.Holidays-City-Breaks)

# Search Holiday Rentals in Winsted
![A tranquil lake with a stone tower, surrounded by autumn-colored trees and a clear sky.](https://images.trvl-media.com/place/3000430645/5a320dbf-5d47-470a-9aa2-d3ad7bb4e67c.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

[Check prices for these dates, 14 – 15 December 2026](https://www.expedia.co.uk/Hotel-Search?regionId=3000430645&startDate=2026-12-14&endDate=2026-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&sort=VACATION%5FRENTAL)

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## Our top choices for Winsted holiday rentals

### [1\. Enjoy a restful stay with fast internet, smart TV and the company of your pet.](https://www.expedia.co.uk/Winsted-Hotels-Enjoy-A-Restful-Stay-With-Fast-Internet.h72396823.Hotel-Information)

![A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396823/e90cda0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

- Location: winsted
- Guest rating: 9.4/10 (Exceptional, 55 reviews)
- Price: £169, includes taxes & fees, 30 Nov - 1 Dec, for Our top choices for Winsted holiday rentals
- Review: It was a nice stay…worked well for the event we attended in town. The host was very nice to work with, by Roberta S.

### [2\. Peaceful and cozy 1 bed 1 bath in quaint Winchester](https://www.expedia.co.uk/Winsted-Hotels-Peaceful-And-Cozy-1-Bed-1-Bath-In-Quaint-Winchester.h132902141.Hotel-Information)

![A wooden cabin interior with a bench, a rug, and a hanging plant.](https://images.trvl-media.com/lodging/133000000/132910000/132902200/132902141/4aa364f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Winchester
- Guest rating: 10/10 (Exceptional, 6 reviews)
- Price: £140, includes taxes & fees, 23 Nov - 24 Nov, for Our top choices for Winsted holiday rentals

### [3\. Cozy Attic 10 min to Llitchfield](https://www.expedia.co.uk/Torrington-Hotels-Cozy-3-Flr-Private-1-Bdrm-Apt-Tree-Line-View.h91304625.Hotel-Information)

![A two-story house with a porch, surrounded by flowering plants.](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/59f8d7dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Torrington
- Guest rating: 9.6/10 (Exceptional, 7 reviews)
- Price: £271, includes taxes & fees, 23 Nov - 24 Nov, for Our top choices for Winsted holiday rentals
- Review: The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy., by Nicole N.

### [4\. Collinsville River Escape / Fall Foliage, Deck & Yard](https://www.expedia.co.uk/Canton-Hotels-Collinsville-River-Escape-Fall-Foliage.h136573706.Hotel-Information)

![A stone fire pit with two Adirondack chairs and a wooden bench, surrounded by a white fence and trees.](https://images.trvl-media.com/lodging/137000000/136580000/136573800/136573706/ceeeeb6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Collinsville
- Guest rating: 9.6/10 (Exceptional, 4 reviews)
- Price: £98, includes taxes & fees, 30 Nov - 1 Dec, for Our top choices for Winsted holiday rentals
- Review: Cute and cozy home away from home! We loved our stay and all the nice features there were!! Everything was neat and clean and host was super amazing and helpful! We definitely will choose this place again if we’re ever in the area., by Leah H.

### [5\. Cozy Modern Farmhouse Private Apt - 3 Beds](https://www.expedia.co.uk/Torrington-Hotels-Cozy-Modern-Farmhouse-Private-2-Bdrm-Apartment.h91304720.Hotel-Information)

![A door with a frosted glass panel featuring a landscape painting, a ceiling fan, and a table with a vase of flowers.](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/547f43df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Torrington
- Guest rating: 10/10 (Exceptional, 4 reviews)
- Price: £311, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winsted holiday rentals
- Review: My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. , by Louisa A.

### [6\. Art House 3 Beds Close to Warner Theater](https://www.expedia.co.uk/Torrington-Hotels-Art-House-3-Beds-Close-To-Warner-Theater.h127214679.Hotel-Information)

![A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.](https://images.trvl-media.com/lodging/128000000/127220000/127214700/127214679/a74b2f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Torrington
- Guest rating: 10/10 (Exceptional, 2 reviews)
- Price: £320, includes taxes & fees, 23 Nov - 24 Nov, for Our top choices for Winsted holiday rentals
- Review: Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. , by Brittany M.

### [7\. Sun Filled Lake House Living](https://www.expedia.co.uk/Avon-Hotels-Sun-Filled-Lake-House-Living.h107960143.Hotel-Information)

![A lakeside picnic area with a bench, two Adirondack chairs, and a picnic table.](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/df3b6996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Avon
- Guest rating: 6.6/10 (4 reviews)
- Price: £191, includes taxes & fees, 16 Nov - 17 Nov, for Our top choices for Winsted holiday rentals
- Review: Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value, by Joseph C.

### [8\. River Overlook - What a view from your deck!](https://www.expedia.co.uk/Canton-Hotels-River-Overlook.h90821015.Hotel-Information)

![A balcony with a view of a lake, white railings, and outdoor furniture.](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/w905h683x59y0-8f890c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Collinsville
- Guest rating: 10/10 (Exceptional, 27 reviews)
- Price: £230, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winsted holiday rentals
- Review: I only did a short stay (2 nights) but it was super adorable! I will definitely stay again when I'm back in the area., by Mary S.

### [9\. Peaceful Meadow Retreat](https://www.expedia.co.uk/Granby-Hotels-Peaceful-Meadow-Retreat.h105660083.Hotel-Information)

![A square fire pit with flames, surrounded by a grassy field and a green chair.](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/df22d08a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Granby
- Guest rating: 10/10 (Exceptional, 26 reviews)
- Review: Great location, quite country yet close to MA and airport., by Todd R.

### [10\. Pristine Cozy Walkable Downtown 2BR Getaway](https://www.expedia.co.uk/Torrington-Hotels-Pristine-Cozy-Walkable-Downtown-2BR-Getaway.h101452935.Hotel-Information)

![A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/74859fe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Torrington
- Guest rating: 10/10 (Exceptional, 22 reviews)
- Price: £207, includes taxes & fees, 16 Nov - 17 Nov, for Our top choices for Winsted holiday rentals
- Review: Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!, by James M.

### [11\. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown](https://www.expedia.co.uk/Torrington-Hotels-Private-Classy-2nd-Flr-3-Bed-Apt-Near-Downtown.h120084697.Hotel-Information)

![A white house with a black front door, a doormat, and a small window above the door.](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084697/eac31e65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Torrington
- Guest rating: 10/10 (Exceptional, 1 review)
- Price: £417, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winsted holiday rentals
- Review: Good communication. Clean place in good location. Would stay again. , by Jaimie S.

### [12\. The Historic Hideaway](https://www.expedia.co.uk/Avon-Hotels-The-Historic-Hideaway.h107901536.Hotel-Information)

![A patio with a white wall, a brick floor, and outdoor furniture including a table and chairs.](https://images.trvl-media.com/lodging/108000000/107910000/107901600/107901536/0abb9e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Avon
- Guest rating: 6/10 (4 reviews)
- Price: £197, includes taxes & fees, 17 Nov - 18 Nov, for Our top choices for Winsted holiday rentals
- Review: House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. , by Nicole M.

### [13\. The Old Avon Village](https://www.expedia.co.uk/Avon-Hotels-The-Old-Avon-Village.h107960210.Hotel-Information)

![A historic building with red brick architecture, snow-covered roofs, and a prominent chimney.](https://images.trvl-media.com/lodging/108000000/107970000/107960300/107960210/7446b875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Avon
- Guest rating: 6.2/10 (10 reviews)
- Price: £201, includes taxes & fees, 16 Nov - 17 Nov, for Our top choices for Winsted holiday rentals
- Review: Great location. Alexander was very responsive to any requests. Met our needs. , by Deborah S.

### [14\. Cozy Cabin Style Apt Private 1st Flr 1 Bdrm](https://www.expedia.co.uk/Torrington-Hotels-Cozy-Cabin-Style-Apt-Private-1st-Flr-1-Bdrm.h120084692.Hotel-Information)

![A wooden wall with a large mirror, a wooden console table, and two wall-mounted lanterns.](https://images.trvl-media.com/lodging/121000000/120090000/120084700/120084692/625a3011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Torrington
- Price: £308, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winsted holiday rentals

### [15\. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville](https://www.expedia.co.uk/Canton-Hotels-Gorgeous-River-Views-On-Rails-To-Trails-And-Just-Steps-To-Quaint-Collinsville.h51685419.Hotel-Information)

![A two-story house with a garage, a driveway, and a river in the background.](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/cd7d0c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Collinsville
- Guest rating: 10/10 (Exceptional, 77 reviews)
- Price: £356, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winsted holiday rentals
- Review: What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. , by Mike

### [16\. Real Estate: Therapy - Lake, Laundry, Love it](https://www.expedia.co.uk/Becket-Hotels-Real-Estate-Therapy-Lake.h128456042.Hotel-Information)

![A spacious living room with a wooden staircase, a dining area, and a television.](https://images.trvl-media.com/lodging/129000000/128460000/128456100/128456042/2d84fb5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Sherwood Forest
- Guest rating: 9.6/10 (Exceptional, 4 reviews)
- Price: £217, includes taxes & fees, 18 Nov - 19 Nov, for Our top choices for Winsted holiday rentals
- Review: Very good trip overall. Great location. Just a few things needed to make it over the top!, by William C B.

### [17\. The Sun Filled Cozy Creamery](https://www.expedia.co.uk/Plainville-Hotels-The-Sun-Filled-Cozy-Creamery.h110371901.Hotel-Information)

![A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/996b1a71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Plainville
- Guest rating: 8.8/10 (Excellent, 28 reviews)
- Price: £185, includes taxes & fees, 29 Nov - 30 Nov, for Our top choices for Winsted holiday rentals
- Review: Very cozy and comfortable.The location was perfect for our stay in the area., by Heather T.

### [18\. Cozy 1-bedroom studio in serene Great Barrington with AC](https://www.expedia.co.uk/Great-Barrington-Hotels-Cozy-1-Bedroom-Studio-In-Serene-Great-Barrington-With-AC.h130975674.Hotel-Information)

![A compact kitchen with a refrigerator, oven, microwave, and coffee maker.](https://images.trvl-media.com/lodging/131000000/130980000/130975700/130975674/76a95c27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Great Barrington
- Guest rating: 8.8/10 (Excellent, 10 reviews)
- Price: £89, includes taxes & fees, 20 Nov - 21 Nov, for Our top choices for Winsted holiday rentals
- Review: great location , berkshires are awesome . very clean , host is excellent ., by bob i.

### [19\. Cozy Camper tucked into the woods](https://www.expedia.co.uk/Sandisfield-Hotels-Cozy-Camper-Tucked-Into-The-Woods.h134908406.Hotel-Information)

![A rural property with a wooden barn, a white fence, and a mobile home.](https://images.trvl-media.com/lodging/135000000/134910000/134908500/134908406/1a305fb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Sandisfield
- Guest rating: 10/10 (Exceptional, 1 review)
- Price: £134, includes taxes & fees, 15 Nov - 16 Nov, for Our top choices for Winsted holiday rentals
- Review: "This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably..., by hannah w.

### [20\. Linny's - Private Dock - Lake Access - Firepit](https://www.expedia.co.uk/Southwick-Hotels-Linnys-West-Suffield-Lake-House.h76320695.Hotel-Information)

![A lakeside property with multiple houses, docks, and a docked boat.](https://images.trvl-media.com/lodging/77000000/76330000/76320700/76320695/1fcca9b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: West Suffield
- Guest rating: 10/10 (Exceptional, 44 reviews)
- Price: £303, includes taxes & fees, 3 Dec - 4 Dec, for Our top choices for Winsted holiday rentals
- Review: Clean, comfortable, peaceful, great hosts!, by Megan D.

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.

[View all properties](https://www.expedia.co.uk/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29&regionId=3000430645&adults=2&sort=VACATION%5FRENTAL&openPlayBack=true)

## Find holiday rentals that suit your style

[Apartments](https://www.expedia.co.uk/Hotel-Search?destination=Winsted,%20Connecticut,%20United%20States%20of%20America&regionId=3000430645&latLong=41.921207,-73.060108&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&lodging=APARTMENT)

[Cabins](https://www.expedia.co.uk/Hotel-Search?destination=Winsted,%20Connecticut,%20United%20States%20of%20America&regionId=3000430645&latLong=41.921207,-73.060108&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&lodging=CABIN)

[Cottages](https://www.expedia.co.uk/Hotel-Search?destination=Winsted,%20Connecticut,%20United%20States%20of%20America&regionId=3000430645&latLong=41.921207,-73.060108&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&lodging=COTTAGE)

[Condos](https://www.expedia.co.uk/Hotel-Search?destination=Winsted,%20Connecticut,%20United%20States%20of%20America&regionId=3000430645&latLong=41.921207,-73.060108&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&lodging=CONDO)

[Chalets](https://www.expedia.co.uk/Hotel-Search?destination=Winsted,%20Connecticut,%20United%20States%20of%20America&regionId=3000430645&latLong=41.921207,-73.060108&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&lodging=CHALET)

## Top Winsted Hotel Reviews

### [Simsbury 1820 House](https://www.expedia.co.uk/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information)

![A large, historic building with a covered porch and outdoor seating area.](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/82b139e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Simsbury Center
- Review: Superb room with 4 poster, lovely owner and excellent value for money, by Tim & Angela, 30 April 2015, rated 10/10 Excellent

### [Truman Gillet House Bed & Breakfast](https://www.expedia.co.uk/Hartford-Hotels-Truman-Gillet-House-Bed-Breakfast.h12986517.Hotel-Information)

![A rural landscape with a red barn, a green house, and autumn foliage.](https://images.trvl-media.com/lodging/13000000/12990000/12986600/12986517/edc2930e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Granby
- Review: Great hosts, beautiful home. Fabulous breakfast., by Matthew, 18 May 2025, rated 10/10 Excellent

### [Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://www.expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

![An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/922406fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Great Barrington
- Review: All good, by Vipada, 27 May 2023, rated 8/10 Good

### [Monument Mountain Motel](https://www.expedia.co.uk/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information)

![A neatly made bed with white linens, two bedside lamps, a nightstand with a telephone, and a painting on the wall.](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/0974da3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Great Barrington
- Review: Being a motel I was worried over what the room would be like. After seeing the room I can say this was one of the best motels I have ever stayed in. The room was clean and a nice size. The bathroom was very large and clean. I would definitely recommend this motel, by Allen, 1 August 2017, rated 10/10 Excellent

### [Holiday Inn Express & Suites Bradley Airport by IHG](https://www.expedia.co.uk/Hartford-Hotels-Holiday-Inn-Express-Suites-Bradley-Airport.h1535956.Hotel-Information)

![A Holiday Inn Express hotel with a covered entrance, multiple floors, and a landscaped driveway.](https://images.trvl-media.com/lodging/2000000/1540000/1536000/1535956/c57c2497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Windsor Locks
- Review: Stayed here for the convenience of Hartford Airport. Did what it needed to do at a reasonable price., by Christopher, 8 June 2026, rated 10/10 Excellent

### [The Farmington Inn & Suites](https://www.expedia.co.uk/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information)

![A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Farmington
- Review: A completely excellent hotel. I would live here. Staff A+. Room A+. Cleaning A+ Reception and its quirky but professional amenities A+ It is even in the 'town centre' so local shops etc are on your door step. The pure luck of finding this place was luck indeed., by Alexander, 9 June 2026, rated 10/10 Excellent

### [Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires](https://www.expedia.co.uk/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information)

![A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Great Barrington
- Review: The hotel was typical 'off the peg' but was very comfortable and offered great facilities. The room was a good size, with everything you would need for a good nights stay. The all you can eat breakfast offered good value, together with 24hr lobby hot drinks was a welcome service after a long drive., by Rob, 4 January 2015, rated 10/10 Excellent

### [Quality Inn Great Barrington](https://www.expedia.co.uk/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

![A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Downtown Great Barrington
- Review: Great one night stay. All amenities in the room were good. Could have done with larger shampoo and lotion bottles. Easy walking to shops and restaurants., by Anonymous traveller, 20 June 2022, rated 10/10 Excellent

### [DoubleTree by Hilton Hotel Bristol, Connecticut](https://www.expedia.co.uk/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information)

![An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/de3a2b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Bristol
- Review: From the moment we walked in to the moment we left the staff could not do enough to help. It was spotlessly clean and the food in the bar was incredible. It’s a shame we live so far away because I would love to take another stay. The friendly staff make this hotel - well done!!!, by Carrie, 23 August 2019, rated 10/10 Excellent

### [Simsbury Inn](https://www.expedia.co.uk/Weatogue-Hotels-Simsbury-Inn.h16756.Hotel-Information)

![A spacious, well-lit event space with a glass ceiling, white tables, and a chandelier.](https://images.trvl-media.com/lodging/1000000/20000/16800/16756/f07e7b76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Simsbury Center
- Review: The hotel is ideally situated for Simsbury based events. The parking is great and the breakfast buffet is very helpful. But the soundproofing between the rooms is awful. We were woken up nightly by other guests using the toilet in nearby rooms., by Cathy, 18 September 2024, rated 8/10 Good

### [Days Inn by Wyndham Torrington](https://www.expedia.co.uk/Torrington-Hotels-Days-Inn-By-Wyndham-Torrington.h49932.Hotel-Information)

![A hotel room with a bed, white pillows, a bedside table with a phone, and a wall-mounted TV displaying a scenic sunset.](https://images.trvl-media.com/lodging/1000000/50000/50000/49932/c8b8e6a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Torrington
- Review: Very helpful front desk, by Jonathan, 21 April 2025, rated 10/10 Excellent

## Find out more about Winsted

**Everything you need to know about** **Winsted** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winsted holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winsted holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

### Winsted holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winsted. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winsted holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Winsted holiday rentals we have selected for you start as low as £1,080 per night. Entering your travel dates in the search wizard you might find even better deals!

### How to find incredible deals on Winsted rentals

At Expedia, we put the best Winsted holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winsted rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winsted holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winsted. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Frequently Asked Questions

### Can I find holiday rentals in Winsted?

Yes, there are holiday rentals in Winsted close to Laurel Lanes, or you can select a more secluded option if you're looking for a relaxing stay.

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

[ Waterfront House & Guest House Available in Winchester, CT!](https://www.expedia.co.uk/Winsted-Hotels-Waterfront-House-Guest-House-Available-In-Winchester.h133132377.Hotel-Information): This highly rated holiday home rental in Winsted is located on a lake, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

### How many holiday rentals are there in Winsted?

With 12 Expedia holiday rentals, you're guaranteed to find just the right place for your Winsted stay.

### What’s there to see and do in Winsted?

Highland Lake and Rowley Fields are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Laurel Lanes. While here, Burr Pond State Park and The Marina at Highland Lake are other places worth a visit.

### What are holiday rentals like in Winsted?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winsted. Holiday rentals feature extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family getaway.

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