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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Winchester vacation 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, (50 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is ￥19,832
￥33,195 total
includes taxes & fees
Aug 9 - Aug 10
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
2 bedrooms, WiFi (free), bed sheets

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 ￥19,549
￥35,152 total
includes taxes & fees
Aug 6 - Aug 7
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
9.2 out of 10, Wonderful, (5 reviews)
The price is ￥15,205
￥44,666 total
includes taxes & fees
Sep 1 - Sep 2
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 ￥22,132
￥67,551 total
includes taxes & fees
Sep 1 - Sep 2
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 ￥20,328
￥52,434 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Modern Farmhouse Private Apt - 3 Beds
Smart TV, fireplace

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 ￥25,184
￥43,324 total
includes taxes & fees
Aug 26 - Aug 27
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 ￥17,566
￥32,557 total
includes taxes & fees
Aug 4 - Aug 5
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 ￥25,971
￥50,289 total
includes taxes & fees
Aug 13 - Aug 14
River Overlook - What a view from your deck!
Outdoor dining

9. 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, (68 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is ￥49,109
￥82,738 total
includes taxes & fees
Aug 10 - Aug 11
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Dining

10. 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)
The price is ￥36,832
￥81,060 total
includes taxes & fees
Aug 17 - Aug 18
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Property grounds

11. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (148 reviews)
"Great location"
United States
Will G.
The price is ￥29,906
￥56,067 total
includes taxes & fees
Aug 3 - Aug 4
Big farmhouse in the foothills of the Berkshires
Interior

12. Linny's - Lakefront Retreat Private Dock & Firepit

Linny's - Lakefront Retreat Private Dock & Firepit
West Suffield
10.0 out of 10, Exceptional, (41 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is ￥27,973
￥57,517 total
includes taxes & fees
Aug 5 - Aug 6
Linny's - Lakefront Retreat Private Dock & Firepit
Interior

13. 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, (11 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is ￥33,841
￥43,482 total
includes taxes & fees
Aug 4 - Aug 5
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
1 bedroom, desk, iron/ironing board, WiFi

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is ￥20,328
￥63,767 total
includes taxes & fees
Aug 17 - Aug 18
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Interior

15. 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 ￥10,861
￥39,780 total
includes taxes & fees
Aug 5 - Aug 6
The Sun Filled Cozy Creamery
Interior

16. 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 ￥14,323
￥45,871 total
includes taxes & fees
Aug 17 - Aug 18
The Historic Hideaway
Coffee/tea maker, fridge, microwave, oven

17. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is ￥45,898
￥59,277 total
includes taxes & fees
Aug 3 - Aug 4
The Jefferson Guest House, Spacious, Special Views
Interior

18. Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (13 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is ￥62,960
￥110,060 total
includes taxes & fees
Aug 4 - Aug 5
Guesthouse Cabin vacation rentals in Berkshire County
Exterior

19. 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 ￥16,684
￥49,365 total
includes taxes & fees
Aug 24 - Aug 25
The Old Avon Village
Outdoor spa tub

20. Bespoke Litchfield - Family Friendly, Hot Tub

Bespoke Litchfield - Family Friendly, Hot Tub
Litchfield
10.0 out of 10, Exceptional, (2 reviews)
"This is a phenomenal location, the house is unparalleled. The host is amazing, friendly, informative, transparent. The house is very well appointed and well cared for. "
United States
Matt S.
Bespoke Litchfield - Family Friendly, Hot Tub
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

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Everything was great! Staff was helpful."
frankie 3-night trip
Posted 6 hours ago
Avon Old Farms Hotel

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?

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR: Visitors give good reviews to this Winchester vacation home rental, which is located on a lake and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings.

How many vacation rentals will I find in Winchester?

Expedia has 10 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, Platt Hill State Park 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.