Default HTG hotel image

Winchester Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
$212 nightly
The price is $240
Sep 1 - Sep 2
Total with taxes and fees
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
$198 nightly
The price is $224
Aug 30 - Aug 31
Total with taxes and fees
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)
"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.
$227 nightly
The price is $269
Sep 1 - Sep 2
Total with taxes and fees
Cozy Attic 10 min to Llitchfield
Exterior

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.
$289 nightly
The price is $343
Aug 27 - Aug 28
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
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.
$377 nightly
The price is $434
Sep 1 - Sep 2
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
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.
$237 nightly
The price is $268
Aug 31 - Sep 1
Total with taxes and fees
Pristine Cozy Walkable Downtown 2BR Getaway
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, (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.
$268 nightly
The price is $303
Aug 27 - Aug 28
Total with taxes and fees
River Overlook - What a view from your deck!
Property grounds

8. 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.
$176 nightly
The price is $199
Sep 10 - Sep 11
Total with taxes and fees
Peaceful Meadow Retreat
Dining

9. 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.
$439 nightly
The price is $521
Aug 30 - Aug 31
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Room

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
$352 nightly
The price is $405
Aug 27 - Aug 28
Total with taxes and fees
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Property grounds

11. 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.
$292 nightly
The price is $314
Sep 9 - Sep 10
Total with taxes and fees
Sun Filled Lake House Living
Interior

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.
$261 nightly
The price is $278
Sep 1 - Sep 2
Total with taxes and fees
The Historic Hideaway
Outdoor dining

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, (70 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
$434 nightly
The price is $491
Sep 10 - Sep 11
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Interior

14. 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.
$239 nightly
The price is $254
Aug 30 - Aug 31
Total with taxes and fees
The Sun Filled Cozy Creamery
Property grounds

15. 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.
$316 nightly
The price is $334
Aug 31 - Sep 1
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Interior

16. 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, (15 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
$246 nightly
The price is $278
Aug 31 - Sep 1
Total with taxes and fees
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Interior

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)
"Perfect, relaxing and easy!"
United States
Wendy C.
$357 nightly
The price is $377
Sep 13 - Sep 14
Total with taxes and fees
Linny's - Private Dock - Lake Access - Firepit
Exterior

18. 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.
$270 nightly
The price is $287
Sep 1 - Sep 2
Total with taxes and fees
The Old Avon Village
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
$398 nightly
The price is $398
Aug 31 - Sep 1
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
Room

20. #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.
#2 *Beautiful 1 BR Apartment - Central CT*
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

The Farmington Inn & Suites

The Farmington Inn & Suites

8/10 Good
"The staff were friendly and helpful, but you have to pay 17.25 a day (even the day you check out) for amenities that we never used. The back door we used looks all scratched up and worn metal door on the bottom. Bad 1st impression. Rooms are prettily decorated with wall paper and curtains that match. 4 poster beds looked great and were comfortable. Breakfast was good with enough choices. English tea bags weren't replenished after one day and don't think they have a designated person to handle only the food area. We left early every day and came back late. It was quiet and clean so recommend it, but be aware you pay for amenities whether you use them or not. Staff were helpful and friendly."
Cynthia 3-night trip
Posted 20 hours ago
The Farmington Inn & Suites

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 $334 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?

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

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, Burr Pond State Park and The Marina at Highland Lake 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.