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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Winchester holiday rentals

Terrace/patio

1. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is HK$988
HK$1,889 total
includes taxes & fees
31 Aug - 1 Sept
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Room

2. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is HK$974
HK$1,767 total
includes taxes & fees
30 Aug - 31 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Exterior

3. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 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
Rhonda H.
The price is HK$716
HK$2,198 total
includes taxes & fees
26 Aug - 27 Aug
Cozy Attic 10 min to Llitchfield
Dining

4. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"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. "
United States
Brittany M.
The price is HK$1,102
HK$3,404 total
includes taxes & fees
31 Aug - 1 Sept
Art House 3 Beds Close to Warner Theater
Exterior

5. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 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
Louisa A.
The price is HK$1,013
HK$2,691 total
includes taxes & fees
31 Aug - 1 Sept
Cozy Modern Farmhouse Private Apt - 3 Beds
Living area

6. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"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!"
United States
James M.
The price is HK$1,254
HK$2,174 total
includes taxes & fees
31 Aug - 1 Sept
Pristine Cozy Walkable Downtown 2BR Getaway
Property grounds

7. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is HK$815
HK$1,561 total
includes taxes & fees
10 Sept - 11 Sept
Peaceful Meadow Retreat
Property grounds

8. River Overlook - What a view from your deck!

River Overlook - What a view from your deck!
Collinsville
10.0 out of 10, Exceptional, (26 reviews)
"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."
United States
Mary S.
The price is HK$1,164
HK$2,372 total
includes taxes & fees
22 Sept - 23 Sept
River Overlook - What a view from your deck!
Property grounds

9. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (4 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is HK$815
HK$2,455 total
includes taxes & fees
9 Sept - 10 Sept
Sun Filled Lake House Living
Exterior

10. The Old Avon Village

The Old Avon Village
Avon
6.2 out of 10, (10 reviews)
"Great location. Alexander was very responsive to any requests. Met our needs. "
United States
Deborah S.
The price is HK$690
HK$2,327 total
includes taxes & fees
1 Sept - 2 Sept
The Old Avon Village
Room

11. Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is HK$1,013
HK$3,176 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Interior

12. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is HK$541
HK$1,989 total
includes taxes & fees
25 Aug - 26 Aug
The Sun Filled Cozy Creamery
Interior

13. The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"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. "
United States
Nicole M.
The price is HK$604
HK$2,167 total
includes taxes & fees
24 Aug - 25 Aug
The Historic Hideaway
Interior

14. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (14 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is HK$1,686
HK$2,181 total
includes taxes & fees
26 Aug - 27 Aug
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Interior

15. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is HK$1,599
HK$3,157 total
includes taxes & fees
13 Sept - 14 Sept
Linny's - Private Dock - Lake Access - Firepit
Outdoor dining

16. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (69 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is HK$2,201
HK$3,848 total
includes taxes & fees
24 Aug - 25 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Property grounds

17. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (149 reviews)
"Great location"
United States
Will G.
The price is HK$1,341
HK$2,619 total
includes taxes & fees
6 Sept - 7 Sept
Big farmhouse in the foothills of the Berkshires
Room

18. #2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
9.0 out of 10, Wonderful, (2 reviews)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
The price is HK$1,250
HK$2,292 total
includes taxes & fees
28 Aug - 29 Aug
#2 *Beautiful 1 BR Apartment - Central CT*
Private kitchen

19. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
The price is HK$2,413
HK$3,119 total
includes taxes & fees
25 Aug - 26 Aug
The Jefferson Guest House, Spacious, Special Views
Property grounds

20. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,936
HK$4,072 total
includes taxes & fees
22 Sept - 23 Sept
Cheerful 3-bedroom cottage with woodstove
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.
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Top Winchester Hotel Reviews

Simsbury 1820 House

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."
Jill 3-night trip
Posted 4 hours ago
Simsbury 1820 House

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester 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 Winchester has to offer?

Lakefront Fall Foliage in New England Just 2 Hours From NYC: This holiday home rental outside of Winchester is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a private garden and a selection of games.

How many holiday rentals will I find in Winchester?

Expedia has 10 holiday rentals for your stay in Winchester.

What’s there to see and do in Winchester?

Highland Lake and Walker Field 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’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family getaway.