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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchester vacation rentals

Interior

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is ￥21,567
￥37,539 total
includes taxes & fees
Oct 4 - Oct 5
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Smart TV, fireplace

2. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (20 reviews)
"It was great!"
United States
Amanda T.
The price is ￥28,539
￥47,674 total
includes taxes & fees
Sep 21 - Sep 22
Pristine Cozy Walkable Downtown 2BR Getaway
Outdoor dining

3. 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, (72 reviews)
"Wow! What a great place! The house is lovely, very clean, comfy beds and cozy seating. Amazing view and an unbeatable location!"
United States
Kristi M.
The price is ￥43,883
￥73,728 total
includes taxes & fees
Sep 20 - Sep 21
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Dining

4. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is ￥36,492
￥90,917 total
includes taxes & fees
Sep 30 - Oct 1
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Dining

5. 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 ￥21,975
￥67,071 total
includes taxes & fees
Sep 20 - Sep 21
Art House 3 Beds Close to Warner Theater
Exterior

6. 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 ￥22,153
￥66,963 total
includes taxes & fees
Oct 7 - Oct 8
Cozy Modern Farmhouse Private Apt - 3 Beds
Property grounds

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

River Overlook - What a view from your deck!
Collinsville
10.0 out of 10, Exceptional, (27 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 ￥25,036
￥47,662 total
includes taxes & fees
Sep 20 - Sep 21
River Overlook - What a view from your deck!
Coffee/tea maker, fridge, microwave, oven

8. 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 ￥45,571
￥58,855 total
includes taxes & fees
Sep 21 - Sep 22
The Jefferson Guest House, Spacious, Special Views
Interior

9. 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, (16 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is ￥33,529
￥42,925 total
includes taxes & fees
Sep 29 - Sep 30
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Interior

10. 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 ￥29,612
￥59,818 total
includes taxes & fees
Oct 14 - Oct 15
Linny's - Private Dock - Lake Access - Firepit
Exterior

11. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 reviews)
"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."
United States
Nicole N.
The price is ￥15,589
￥56,041 total
includes taxes & fees
Oct 7 - Oct 8
Cozy Attic 10 min to Llitchfield
Property grounds

12. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (151 reviews)
"Great location"
United States
Will G.
The price is ￥29,631
￥54,893 total
includes taxes & fees
Sep 22 - Sep 23
Big farmhouse in the foothills of the Berkshires
Property grounds

13. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (44 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥29,115
￥68,832 total
includes taxes & fees
Oct 12 - Oct 13
Cheerful 3-bedroom cottage with woodstove
2 bedrooms, WiFi, bed sheets

14. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is ￥34,247
￥53,235 total
includes taxes & fees
Sep 21 - Sep 22
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Property grounds

15. 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 ￥16,253
￥30,803 total
includes taxes & fees
Oct 5 - Oct 6
Peaceful Meadow Retreat
Outdoor dining

16. Prime West Hartford Center Location: Historic Gem

Prime West Hartford Center Location: Historic Gem
West Hartford
10.0 out of 10, Exceptional, (35 reviews)
"We loved being so close to downtown West Hartford. The house had everything we needed for a fun graduation weekend."
United States
Trish
The price is ￥65,656
￥109,199 total
includes taxes & fees
Oct 4 - Oct 5
Prime West Hartford Center Location: Historic Gem
TV

17. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is ￥44,071
￥90,192 total
includes taxes & fees
Sep 21 - Sep 22
Treetop Hideaway in Tyringham
Apartment (1 Bedroom) | Interior

18. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is ￥27,291
￥48,935 total
includes taxes & fees
Sep 29 - Sep 30
Bristol Condo Near Espn HQ & Lake Compounce!
Interior

19. Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT

Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Bloomfield
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Outdoor dining

20. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
The price is ￥23,911
￥30,548 total
includes taxes & fees
Sep 23 - Sep 24
Cozy Camper tucked into the woods
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
"Gorgeous little place to stay in a lovely town. Would have eaten there had the restaurant not been closed On Sunday and Monday when I was visiting! Would like some hot vegetarian breakfast options (all the hot sandwiches had meat in), the fresh baked goods were delicious! Bathroom was in need of a clean, handles felt sticky. Everyone was so friendly and it was a very comfortable stay. Will come back!"
Melanie Claire 2-night trip
Posted 6 hours ago
Simsbury 1820 House

Find out more about Winchester

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Frequently asked questions

Are there vacation rentals in Winchester?

Yes, there are vacation rentals in Winchester close to Laurel Lanes, or you can choose a more remote option if you're looking for extra privacy while you relax.

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

Waterfront House & Guest House Available in Winchester, CT!: Visitors give good reviews to this Winchester vacation home rental, which 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 vacation rentals will I find in Winchester?

Expedia has 11 vacation 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, The Marina at Highland Lake and Burr Pond State Park are other places worth a visit.

What’s a vacation rental in Winchester like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Winchester. Vacation rentals offer extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family trips.