Title: Winchester Vacation Rentals from $340: Search Short-Term Rentals | Expedia.com

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![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=553248635975869849&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=553248635975869849&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=553248635975869849&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=553248635975869849&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester vacation rentals

![Property grounds](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/df22d08a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/9f68233b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/4a573ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/5bf6da4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Meadow Retreat

[](https://www.expedia.com/Granby-Hotels-Peaceful-Meadow-Retreat.h105660083.Hotel-Information)

Granby

10/10

Exceptional

(18 reviews)

"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kaleigh L.

$155 nightly

$175 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Granby-Hotels-Peaceful-Meadow-Retreat.h105660083.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/eab09613.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/970a479f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/ba8d6f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/db89ae2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

[](https://www.expedia.com/Torrington-Hotels-Cozy-3-Flr-Private-1-Bdrm-Apt-Tree-Line-View.h91304625.Hotel-Information)

Torrington

9.2/10

Wonderful

(5 reviews)

"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rhonda H.

$295 nightly

$339 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Torrington-Hotels-Cozy-3-Flr-Private-1-Bdrm-Apt-Tree-Line-View.h91304625.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/76ed01a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/a8bdd677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/349b6d9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/f02ef755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Townhome | Perfect for Family Gatherings & Events

[](https://www.expedia.com/Bloomfield-Hotels-Stylish-Townhome-Perfect-For-Family-Gatherings-Events.h108188444.Hotel-Information)

Bloomfield

10/10

Exceptional

(5 reviews)

"The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Muhammad G.

$619 nightly

$701 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Bloomfield-Hotels-Stylish-Townhome-Perfect-For-Family-Gatherings-Events.h108188444.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/f5b911c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/4ba12a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/6f1f9830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/w1512h1050x0y79-c667dc04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Litchfield Retreat, Wineries, Foliage & Skiing

[](https://www.expedia.com/Torrington-Hotels-Litchfield-Retreat.h122835857.Hotel-Information)

Torrington

$348 nightly

$395 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Torrington-Hotels-Litchfield-Retreat.h122835857.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/108000000/107910000/107901600/107901536/f4da917b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107910000/107901600/107901536/b7011e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107910000/107901600/107901536/f5c5af93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107910000/107901600/107901536/4d11d50d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Historic Hideaway

[](https://www.expedia.com/Avon-Hotels-The-Historic-Hideaway.h107901536.Hotel-Information)

Avon

6.0/10

(4 reviews)

"Once we found the house it was very warm & cozy. The mini- muffins on the counter was a bonus. House mailbox was 87 but address was 89 that you only see if door is closed which it wasn't on 1st 2 passes. Limited exterior lights made coming back at night a challenge. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kim C.

$252 nightly

$268 total

Mar 27 - Mar 28

Total with taxes and fees

[](https://www.expedia.com/Avon-Hotels-The-Historic-Hideaway.h107901536.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/3db87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/bf37a122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/979641d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/68707c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### CT Gate House Goshen CT, Gate House Goshen CT

[](https://www.expedia.com/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information)

Goshen

9.4/10

Exceptional

(9 reviews)

"The property was great and the house was huge even for all 12 of us "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ryan L.

$624 nightly

$640 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/w905h683x59y0-8f890c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/eba05f8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/w904h683x60y0-a0d1107c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/39eb1814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Overlook - Check the view from your deck!

[](https://www.expedia.com/Canton-Hotels-River-Overlook.h90821015.Hotel-Information)

Collinsville

10/10

Exceptional

(23 reviews)

"The place was perfect for the two of us. It was close to both our kids homes."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tomas M.

$254 nightly

$288 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Canton-Hotels-River-Overlook.h90821015.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/7dd95cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/dc8af495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/74859fe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/a550b105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pristine Cozy Walkable Downtown 2BR Getaway

[](https://www.expedia.com/Torrington-Hotels-Pristine-Cozy-Walkable-Downtown-2BR-Getaway.h101452935.Hotel-Information)

Torrington

10/10

Exceptional

(17 reviews)

"What a comfortable and welcoming place to stay! Great communication with the hosts, and the space had all the amenities we needed, as well as many thoughtful extra touches. Home was spotless, and tastefully decorated. Quiet neighborhood, and super easy access to downtown. Would absolutely stay here again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kathryn A.

$266 nightly

$266 total

Mar 27 - Mar 28

Total with taxes and fees

[](https://www.expedia.com/Torrington-Hotels-Pristine-Cozy-Walkable-Downtown-2BR-Getaway.h101452935.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/51b9c734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/a764aae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/d00ad195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Guesthouse Cabin vacation rentals in Berkshire County

[](https://www.expedia.com/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information)

Sheffield

10/10

Exceptional

(10 reviews)

"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

deborah d.

$629 nightly

$703 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/7377fc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/b924c628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/0f27818f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/2350af4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Big farmhouse in the foothills of the Berkshires

[](https://www.expedia.com/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information)

Russell

10/10

Exceptional

(143 reviews)

"The house is absolutely charming and cozy. It was very clean as well. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amanda C.

$322 nightly

$340 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/94000000/93250000/93241000/93240974/2df3c8c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/94000000/93250000/93241000/93240974/7f9074d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93250000/93241000/93240974/0766039e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93250000/93241000/93240974/446492ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dugway Hideaway Walking Distance to Lime Rock Park

[](https://www.expedia.com/Falls-Village-Hotels-Dugway-Hideaway-Walking-Distance-To-Lime-Rock-Park.h93240974.Hotel-Information)

Salisbury

9.2/10

Wonderful

(15 reviews)

"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brig

$279 nightly

$309 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Falls-Village-Hotels-Dugway-Hideaway-Walking-Distance-To-Lime-Rock-Park.h93240974.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/89d11901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/abd1a92f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/547f43df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304800/91304720/9b25a8e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Modern Farmhouse Private Apt - 3 Beds

[](https://www.expedia.com/Torrington-Hotels-Cozy-Modern-Farmhouse-Private-2-Bdrm-Apartment.h91304720.Hotel-Information)

Torrington

10/10

Exceptional

(4 reviews)

"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. "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Louisa A.

$346 nightly

$399 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Torrington-Hotels-Cozy-Modern-Farmhouse-Private-2-Bdrm-Apartment.h91304720.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/128000000/127220000/127214700/127214679/0ef34e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/128000000/127220000/127214700/127214679/f1b0ef39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/128000000/127220000/127214700/127214679/fc820725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/128000000/127220000/127214700/127214679/7b457a6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Art House 3 Beds Close to Warner Theater

[](https://www.expedia.com/Torrington-Hotels-Art-House-3-Beds-Close-To-Warner-Theater.h127214679.Hotel-Information)

Torrington

$323 nightly

$377 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Torrington-Hotels-Art-House-3-Beds-Close-To-Warner-Theater.h127214679.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/e982edfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/1c343d33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/c726dcdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, stereo](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/30745e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Jefferson Guest House, Spacious, Special Views

[](https://www.expedia.com/Litchfield-Hotels-The-Jefferson-House.h111926107.Hotel-Information)

Litchfield

10/10

Exceptional

(8 reviews)

"The place was absolutely spotless and magnificent in every way. Highly recommended."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert A.

$373 nightly

$373 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Litchfield-Hotels-The-Jefferson-House.h111926107.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279234/dee9e184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279234/0de00917.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279234/f9e14ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99280000/99279300/99279234/9f8d3ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

[](https://www.expedia.com/Plainville-Hotels-3-FRESHLY-REDONE-NEWLY-FURNISHED-A-MUST-SEE.h99279234.Hotel-Information)

Plainville

8.4/10

Very Good

(12 reviews)

"Great place ! Quiet and safe place! We will be back! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Aubrey C.

$336 nightly

$362 total

Mar 27 - Mar 28

Total with taxes and fees

[](https://www.expedia.com/Plainville-Hotels-3-FRESHLY-REDONE-NEWLY-FURNISHED-A-MUST-SEE.h99279234.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/c79da4f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/df3b6996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/5d0d5824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/5ac312e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun Filled Lake House Living

[](https://www.expedia.com/Avon-Hotels-Sun-Filled-Lake-House-Living.h107960143.Hotel-Information)

Avon

6.0/10

(3 reviews)

"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joseph C.

$244 nightly

$259 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Avon-Hotels-Sun-Filled-Lake-House-Living.h107960143.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/e3f04cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/d96d2729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/c8b2ae4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/129a2984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treetop Hideaway in Tyringham

[](https://www.expedia.com/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.Hotel-Information)

Monterey

9.0/10

Wonderful

(10 reviews)

"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah B.

$530 nightly

$560 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/e6a8de71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/07647859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/9f6d0429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/4ac89d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

[](https://www.expedia.com/Goshen-Hotels-Sequoia-House-Charming-Goshen-Getaway-Quiet-Retreat-In-Litchfield-Hills.h123028859.Hotel-Information)

Goshen

10/10

Exceptional

(1 review)

"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linda D.

$520 nightly

$590 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Goshen-Hotels-Sequoia-House-Charming-Goshen-Getaway-Quiet-Retreat-In-Litchfield-Hills.h123028859.Hotel-Information)

![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/fe9d9847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/15697af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/c22e2a2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/d25ce94c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dainty New Preston Cottage w/ Dock & Lake Views!

[](https://www.expedia.com/New-Preston-Hotels-Dainty-New-Preston-Cottage-W-Dock-Lake-Views.h94953757.Hotel-Information)

New Preston

$449 nightly

$517 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/New-Preston-Hotels-Dainty-New-Preston-Cottage-W-Dock-Lake-Views.h94953757.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/3e6e58ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/ab946d75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cheerful 3-bedroom cottage with woodstove

[](https://www.expedia.com/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information)

Sheffield

10/10

Exceptional

(42 reviews)

"The property was centrally located for skiing, and was a comfortable stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelly R.

$454 nightly

$507 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information)

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://expedia.com/Hotel-Search?startDate=2026-04-06&endDate=2026-04-07&regionId=553248635975869849&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Connecticut%2C+United+States+of+America&regionId=553248635975869849&latLong=41.935764%2C-73.111359&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Connecticut%2C+United+States+of+America&regionId=553248635975869849&latLong=41.935764%2C-73.111359&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Connecticut%2C+United+States+of+America&regionId=553248635975869849&latLong=41.935764%2C-73.111359&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Connecticut%2C+United+States+of+America&regionId=553248635975869849&latLong=41.935764%2C-73.111359&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Connecticut%2C+United+States+of+America&regionId=553248635975869849&latLong=41.935764%2C-73.111359&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=VILLA)

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## Top Winchester Hotel Reviews

![Sheraton Hartford Hotel at Bradley Airport](https://images.trvl-media.com/lodging/1000000/10000/4700/4632/81dcef8a_y.jpg)

### Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent

"Great when flying out early in the morning. Nothing more convenient. Rooms are clean, comfortable and updated."

[](https://expedia.com/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information)

![Fairfield Inn & Suites by Marriott Plainville](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/ac051f95_y.jpg)

### Fairfield Inn & Suites by Marriott Plainville

6/10 Okay

"NO HOT WATER!"

[](https://expedia.com/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information)

![Hampton Inn & Suites Hartford/Farmington](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/f9413aba_y.jpg)

### Hampton Inn & Suites Hartford/Farmington

10/10 Excellent

"Wonderful hot breakfast with fresh fruit. Large rooms and very comfortable bed. Great value in the Hartford area."

[](https://expedia.com/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information)

![The Litchfield Inn](https://images.trvl-media.com/lodging/5000000/4980000/4978900/4978856/da1dad71_y.jpg)

### The Litchfield Inn

4/10 Poor

"Not a 4star property. It is all rather tired. We expected our room to be made up each day - didn’t happen. Breakfast comprised of stale pastries, sausage patties and potatoes that were barely warm and had been standing for too long. The coffee was undrinkable it was all counter service and clear your own table Not 4 star standard by any stretch of the imagination. Bed was very soft so we did not sleep well and left after breakfast today feeling nauseous "

[](https://expedia.com/Torrington-Hotels-The-Litchfield-Inn.h4978856.Hotel-Information)

![DoubleTree by Hilton Hotel Bristol, Connecticut](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/de3a2b5f_y.jpg)

### DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent

"Great food"

[](https://expedia.com/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information)

![Interlaken Inn & Resort](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/dbbfdf3a_y.jpg)

### Interlaken Inn & Resort

10/10 Excellent

"Overall great amenities and great price"

[](https://expedia.com/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.Hotel-Information)

![Residence Inn by Marriott Hartford Avon](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/27e9804b_y.jpg)

### Residence Inn by Marriott Hartford Avon

10/10 Excellent

"To much noise by the elevator area on ground floor."

[](https://expedia.com/Hartford-Hotels-Residence-Inn-By-Marriott-Hartford-Avon.h1074390.Hotel-Information)

![Delamar West Hartford](https://images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2_y.jpg)

### Delamar West Hartford

10/10 Excellent

"I was pretty surprised at how clean, walkable and nice west Hartford was. Easy to find a spot for dinner nearby. The hotel and staff are great. It’s more expensive but this is a case of getting what I paid for. I have zero complaints about my stay"

[](https://expedia.com/Hartford-Hotels-Delamar-West-Hartford.h18166744.Hotel-Information)

![The Farmington Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg)

### The Farmington Inn & Suites

10/10 Excellent

"Very good place thank you"

[](https://expedia.com/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information)

## Find out more about Winchester

**Everything you need to know about Winchester vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Winchester vacation rentals: An excellent choice for every season**

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $340 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Winchester rentals**

At Expedia, we put the best Winchester vacation 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 Winchester 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 Winchester vacation.

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

## Explore a world of travel with Expedia

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- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Winchester ](https://expedia.com/Winchester-Private-Vacation-Homes.d553248635975869849-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.com/Winchester-Cottages.d553248635975869849-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.com/Winchester-Apartments.d553248635975869849-aaApartments.Travel-Guide-Accommodation)
- [Farmstay in Winchester ](https://expedia.com/Winchester-Agritourism.d553248635975869849-aaAgritourism.Travel-Guide-Accommodation)
- [Cabin Rentals in Winchester ](https://expedia.com/Winchester-Cabins.d553248635975869849-aaCabins.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.com/Winchester-Bed-And-Breakfast.d553248635975869849-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Winchester ](https://expedia.com/Winchester-Guest-Houses.d553248635975869849-aaGuestHouses.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.com/Winchester-Motels.d553248635975869849-aaMotels.Travel-Guide-Accommodation)
- [Inns in Winchester ](https://expedia.com/Winchester-Inns.d553248635975869849-aaInns.Travel-Guide-Accommodation)
- [Condo Rentals in Winchester ](https://expedia.com/Winchester-Condos.d553248635975869849-aaCondos.Travel-Guide-Accommodation)
- [Chalets in Winchester ](https://expedia.com/Winchester-Chalets.d553248635975869849-aaChalets.Travel-Guide-Accommodation)
- [Villas in Winchester ](https://expedia.com/Winchester-Villas.d553248635975869849-aaVillas.Travel-Guide-Accommodation)
- [Resorts in Winchester ](https://expedia.com/Winchester-Resorts.d553248635975869849-aaResorts.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Winchester?

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

### How many vacation rentals will I find in Winchester?

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

### What’s a vacation rental in Winchester like?