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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winchester vacation rentals

A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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, (55 reviews)
"Clean property, very cute. Also very small. Cable/tv access was challenging, but all on all a good experience"
United States
traci
The price is AED 463
AED 874 total
includes taxes & fees
12 Oct - 13 Oct
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is AED 422
AED 774 total
includes taxes & fees
1 Nov - 2 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A two-story house with a front porch, a small balcony, and a white picket fence.

3. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 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 AED 444
AED 1,432 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Attic 10 min to Llitchfield
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

4. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (22 reviews)
"It was great!"
United States
Amanda T.
The price is AED 621
AED 1,053 total
includes taxes & fees
5 Nov - 6 Nov
Pristine Cozy Walkable Downtown 2BR Getaway
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

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 AED 526
AED 1,607 total
includes taxes & fees
2 Nov - 3 Nov
Art House 3 Beds Close to Warner Theater
A wooden wall with a large mirror, a wooden console table, and two wall-mounted lanterns.

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is AED 513
AED 1,533 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

7. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
10.0 out of 10, Exceptional, (1 review)
"We loved the place, which feels like your own house in the woods. The setting is gorgeous especially with the leaves changing colors. We specifically chose the location so we could bike the Farmington Trail loop which starts at the bottom of the hill. The house is so well stocked with everything you could think of, especially coffee and there is plenty of space to relax inside and out. The host was very attentive to our needs. It couldn’t have been better for us."
United States
Margaret A.
The price is AED 585
AED 746 total
includes taxes & fees
20 Oct - 21 Oct
Collinsville River Escape / Fall Foliage, Deck & Yard
A balcony with a view of a lake, white railings, and outdoor furniture.

8. 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 AED 654
AED 1,236 total
includes taxes & fees
12 Oct - 13 Oct
River Overlook - What a view from your deck!
A two-story house with a front porch, a small balcony, and a white picket fence.

9. 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.
Cozy Modern Farmhouse Private Apt - 3 Beds
A square fire pit with flames, surrounded by a grassy field and a green chair.

10. 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 AED 344
AED 680 total
includes taxes & fees
12 Oct - 13 Oct
Peaceful Meadow Retreat
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

11. 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, (18 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AED 790
AED 1,011 total
includes taxes & fees
12 Oct - 13 Oct
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A patio with a table and chairs, a grill, and a view of a lake.

12. 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, (73 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AED 1,146
AED 1,931 total
includes taxes & fees
20 Oct - 21 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

13. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 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...
United States
hannah w.
The price is AED 588
AED 739 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Camper tucked into the woods
A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

14. 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 AED 268
AED 983 total
includes taxes & fees
12 Oct - 13 Oct
The Historic Hideaway
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

15. 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 AED 1,131
AED 1,450 total
includes taxes & fees
29 Oct - 30 Oct
The Jefferson Guest House, Spacious, Special Views
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

16. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (54 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is AED 900
AED 2,072 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Cottage-Sunset On The Lake
A spacious kitchen with a large island, wooden beams, and pendant lighting.

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

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were very clean with a warm homey feel. We would definitely stay here again."
United States
Patricia S.
Linny's - Private Dock - Lake Access - Firepit
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

18. 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 AED 268
AED 983 total
includes taxes & fees
26 Oct - 27 Oct
Sun Filled Lake House Living
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

19. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is AED 1,539
AED 2,554 total
includes taxes & fees
21 Oct - 22 Oct
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

20. 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 AED 253
AED 921 total
includes taxes & fees
14 Oct - 15 Oct
The Sun Filled Cozy Creamery
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
"Lovely comfortable place!!"
Susan 2-night trip
Posted 2 days ago
Simsbury 1820 House

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.