Apartments in Winchester for Rent

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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Winchester apartments

Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Torrington

9.6 out of 10, Exceptional, (4)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
$301 nightly
The price is $345
Dec 10 - Dec 11
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Terrace/patio
Peaceful Meadow Retreat

Apartment in Granby

2.0 star property
10.0 out of 10, Exceptional, (16)
"The place is beautiful and very quiet and relaxing"
United States
Marian
$174 nightly
The price is $197
Jan 6 - Jan 7, 2026
Total with taxes and fees
Peaceful Meadow Retreat
Outdoor dining
The Historic Hideaway

Apartment in Avon

2.0 star property
7.0 out of 10, Good, (2)
"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.
$233 nightly
The price is $245
Dec 10 - Dec 11
Total with taxes and fees
The Historic Hideaway
Exterior
Cozy Modern Farmhouse Private Apt - 3 Beds

Apartment in Torrington

10.0 out of 10, Exceptional, (4)
"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.
$333 nightly
The price is $383
Dec 10 - Dec 11
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
Fridge, microwave, oven, stovetop
Charming apartment 7 minute walk to downtown

Apartment in Torrington

10.0 out of 10, Exceptional, (15)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
$229 nightly
The price is $260
Dec 11 - Dec 12
Total with taxes and fees
Charming apartment 7 minute walk to downtown
Fridge, microwave, oven, stovetop
River Overlook - Check the view from your deck!

Apartment in Collinsville

10.0 out of 10, Exceptional, (23)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
$253 nightly
The price is $286
Dec 10 - Dec 11
Total with taxes and fees
River Overlook - Check the view from your deck!
Fridge, microwave, oven, stovetop
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

Apartment in Plainville

8.4 out of 10, Very Good, (12)
"We enjoyed staying here. Great place, good communication, and a good rate for the space."
United States
Daniel F.
$264 nightly
The price is $280
Dec 18 - Dec 19
Total with taxes and fees
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Interior
#31 - Downtown Terryville- 1 Br

Apartment in Plymouth

10.0 out of 10, Exceptional, (1)
"In convenient safe area. Os is easy to contact"
United States
Gina P.
$268 nightly
The price is $289
Dec 22 - Dec 23
Total with taxes and fees
#31 - Downtown Terryville- 1 Br
Interior
The Sun Filled Cozy Creamery

Apartment in Plainville

8.8 out of 10, Excellent, (24)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
$360 nightly
The price is $397
Dec 25 - Dec 26
Total with taxes and fees
The Sun Filled Cozy Creamery
Exterior
The Old Avon Village

Apartment in Avon

2.0 star property
6.2 out of 10, (10)
"My unit was exactly as described. I thoroughly enjoyed my stay and will definitely return again. "
United States
Carol S.
$282 nightly
The price is $302
Dec 10 - Dec 11
Total with taxes and fees
The Old Avon Village
1 bedroom, desk, iron/ironing board, WiFi
The Jefferson Guest House, Spacious, Special Views

Apartment in Litchfield

10.0 out of 10, Exceptional, (8)
"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.
$375 nightly
The price is $375
Dec 10 - Dec 11
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
Exterior
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Apartment in Torrington

$333 nightly
The price is $383
Dec 10 - Dec 11
Total with taxes and fees
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
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

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Clean room, staff were friendly, helpful and kind. Quiet even with planes landing right next door. Can't compliment this place enough."
Christine 1-night trip
Posted 1 day ago
Sheraton Hartford Hotel at Bradley Airport

Find out more about Winchester

Winchester Apartments information

Number of reviews
118
Accommodation
62 Apartments
Lowest Price
$197
Highest Price
$397

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: The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock: Includes free WiFi, private patios, and private yards. The Sun Filled Cozy Creamery: Located 22.1 mi/35.6 km away in Plainville. Amenities include private balconies. Access to onsite laundry facilities is available on site. Steele Brook Manor Tranquil get away nestled in Litchfield County.: Located in Watertown, 22.3 mi/35.9 km away. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Litchfield Hills Hideaway: 15.1 mi/24.2 km away in Litchfield. Amenities include private patios.
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.

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