Default HTG hotel image

Search Apartment Rentals in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winchester apartments

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)
"It was a nice stay…worked well for the event we attended in town. The host was very nice to work with"
United States
Roberta S.
The price is CA $153
CA $294 total
includes taxes & fees
Nov 22 - Nov 23
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
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.
The price is CA $148
CA $504 total
includes taxes & fees
Nov 10 - Nov 11
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.
The price is CA $214
CA $594 total
includes taxes & fees
Nov 10 - Nov 11
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.
The price is CA $199
CA $578 total
includes taxes & fees
Nov 10 - Nov 11
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)
"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 CA $244
CA $399 total
includes taxes & fees
Nov 16 - Nov 17
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.
The price is CA $338
CA $808 total
includes taxes & fees
Nov 10 - Nov 11
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A wooden wall with a large mirror, a wooden console table, and two wall-mounted lanterns.

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is CA $199
CA $559 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
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 CA $226
CA $428 total
includes taxes & fees
Nov 10 - Nov 11
River Overlook - What a view from your deck!
A square fire pit with flames, surrounded by a grassy field and a green chair.

9. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (26 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is CA $132
CA $242 total
includes taxes & fees
Nov 11 - Nov 12
Peaceful Meadow Retreat
A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

10. 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 CA $103
CA $364 total
includes taxes & fees
Nov 17 - Nov 18
The Historic Hideaway
A historic building with red brick architecture, snow-covered roofs, and a prominent chimney.

11. 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 CA $109
CA $379 total
includes taxes & fees
Nov 16 - Nov 17
The Old Avon Village
A spacious kitchen with wooden cabinets, a large island with stools, and a clock on the wall.

12. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 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 CA $435
CA $534 total
includes taxes & fees
Nov 10 - Nov 11
The Jefferson Guest House, Spacious, Special Views
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

13. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
8.8 out of 10, Excellent, (28 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is CA $97
CA $330 total
includes taxes & fees
Nov 29 - Nov 30
The Sun Filled Cozy Creamery
A two-story house with a stone staircase leading to the front porch.

14. 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, (21 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is CA $304
CA $376 total
includes taxes & fees
Nov 10 - Nov 11
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
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 Litchfield Inn

The Litchfield Inn

10/10 Excellent
"We really enjoyed our stay. Room was clean and quiet."
Philip 1-night trip
Posted 13 hours ago
The Litchfield Inn

Find out more about Winchester

Winchester Apartments information

Number of reviews
157
Accommodation
66 Apartments
Lowest Price
CA $242
Highest Price
CA $808

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can search through 5 apartments in Winchester for your vacation.
Are you thinking about an apartment for your stay?
An apartment features a kitchen for convenient meals, and is often more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, but also for families wanting the conveniences of home.
What's a favorite apartment I should consider for a stay in Winchester?
Listed below are some of the favorite apartments in the area to choose from: Enjoy a restful stay with fast internet, smart TV and the company of your pet.: Includes free WiFi, private patios, and fireplaces. Access to a hot tub is available on site. River Overlook - What a view from your deck!: Located 13 mi/20.9 km away in Canton. Private patios and Smart TVs are included. West Hartford Center 1st floor: Located in West Hartford, 22.7 mi/36.5 km away. Includes free WiFi. Access to onsite laundry facilities is available on site. The Overlook near South Farms in Litchfield County is Hospitality, integrated.: It's located in Morris, 17.4 mi/28.1 km from Winchester. Includes free WiFi, private patios, and Smart TVs.
How many apartments can I expect to find in Winchester?
Expedia has 5 apartments to book in Winchester.
What can I expect from the weather in Winchester?
Weather is only one factor, but it can really affect your travel plans, especially if you're planning an extended stay in Winchester. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What should I see and do in Winchester?
Highland Lake and Walker Field are a couple of scenic spots to enjoy the outdoors, whereas Winchester Historical Society is one of the cultural attractions. While here, The Marina at Highland Lake and Burr Pond State Park are other places worth a visit.
What's the best way to get to and around Winchester?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Bradley Intl. Airport (BDL), which is located 21.9 mi (35.2 km) from the heart of the city. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia