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Winchester Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winchester vacation rentals

A wooden cabin interior with a bench, a rug, and a hanging plant.

1. 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, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
$174 nightly
The price is $197
Nov 1 - Nov 2
Total with taxes and fees
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.

2. 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.
$321 nightly
The price is $369
Oct 25 - Oct 26
Total with taxes and fees
Cozy Attic 10 min to Llitchfield
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

3. 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.
$385 nightly
The price is $445
Oct 25 - Oct 26
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
A two-story house with a front porch, a small balcony, and a white picket fence.

4. 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.
$369 nightly
The price is $425
Oct 27 - Oct 28
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

5. 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.
$253 nightly
The price is $287
Nov 18 - Nov 19
Total with taxes and fees
Pristine Cozy Walkable Downtown 2BR Getaway
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

6. 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.
$508 nightly
The price is $591
Oct 25 - Oct 26
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A balcony with a view of a lake, white railings, and outdoor furniture.

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.
$297 nightly
The price is $336
Oct 25 - Oct 26
Total with taxes and fees
River Overlook - What a view from your deck!
A wooden wall with a large mirror, a wooden console table, and two wall-mounted lanterns.

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
$363 nightly
The price is $419
Oct 25 - Oct 26
Total with taxes and fees
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

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.
$248 nightly
The price is $263
Oct 26 - Oct 27
Total with taxes and fees
Sun Filled Lake House Living
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.
$164 nightly
The price is $185
Oct 28 - Oct 29
Total with taxes and fees
Peaceful Meadow Retreat
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

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

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
9.4 out of 10, Exceptional, (3 reviews)
"This was a great weekend away in CT! The house was comfortable and clean. Very cozy setup and good communication with the host. The weather wasn’t amazing but we still enjoyed our stay for the weekend."
United States
Brandon R.
$195 nightly
The price is $221
Nov 2 - Nov 3
Total with taxes and fees
Collinsville River Escape / Fall Foliage, Deck & Yard
A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

12. 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.
$254 nightly
The price is $270
Oct 26 - Oct 27
Total with taxes and fees
The Historic Hideaway
A patio with a table and chairs, a grill, and a view of a lake.

13. 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, (74 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
$464 nightly
The price is $526
Oct 29 - Oct 30
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A compact RV interior with a kitchenette, a sofa with patterned upholstery, and a window with a view.

14. 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.
$164 nightly
The price is $183
Oct 27 - Oct 28
Total with taxes and fees
Cozy Camper tucked into the woods
A historic building with red brick architecture, snow-covered roofs, and a prominent chimney.

15. 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.
$261 nightly
The price is $277
Nov 4 - Nov 5
Total with taxes and fees
The Old Avon Village
A living room with a fireplace, bookshelves, a television, and a comfortable seating area.

16. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
$395 nightly
The price is $448
Oct 25 - Oct 26
Total with taxes and fees
Sharon Retreat w/ Private Yard
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

17. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (27 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
$238 nightly
The price is $253
Nov 16 - Nov 17
Total with taxes and fees
The Sun Filled Cozy Creamery
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

18. 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.
$574 nightly
The price is $650
Nov 10 - Nov 11
Total with taxes and fees
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A spacious kitchen with wooden cabinets, a large island with stools, and a clock on the wall.

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
$395 nightly
The price is $395
Oct 27 - Oct 28
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

20. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (55 reviews)
"Quiet and peaceful"
United States
Michael S.
$515 nightly
The price is $575
Oct 23 - Oct 24
Total with taxes and fees
Cozy Cottage-Sunset On The Lake
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

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Hotel was clean and modern. Hotel bar was fun and front desk was quick, friendly and efficient."
Jennifer 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut

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 $197 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.

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.