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Our top choices for Winchester apartments

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (17 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is CA $128
CA $252 total
includes taxes & fees
Feb 23 - Feb 24
Peaceful Meadow Retreat

River Overlook - Check the view from your deck!

River Overlook - Check the view from your deck!
Collinsville
10.0 out of 10, Exceptional, (23 reviews)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
The price is CA $183
CA $367 total
includes taxes & fees
Feb 19 - Feb 20
River Overlook - Check the view from your deck!

Pristine, Walkable downtown, Entire 2 Bedroom apartment

Pristine, Walkable downtown, Entire 2 Bedroom apartment
Torrington
10.0 out of 10, Exceptional, (16 reviews)
"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.
The price is CA $230
CA $403 total
includes taxes & fees
Mar 11 - Mar 12
Pristine, Walkable downtown, Entire 2 Bedroom apartment

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"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.
The price is CA $109
CA $451 total
includes taxes & fees
Feb 19 - Feb 20
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"The place was absolutely spotless and magnificent in every way. Highly recommended."
United States
Robert A.
The price is CA $398
CA $515 total
includes taxes & fees
Feb 19 - Feb 20
The Jefferson Guest House, Spacious, Special Views

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 $165
CA $532 total
includes taxes & fees
Feb 19 - Feb 20
Cozy Modern Farmhouse Private Apt - 3 Beds

Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is CA $273
CA $430 total
includes taxes & fees
Mar 1 - Mar 2
Dugway Hideaway Walking Distance to Lime Rock Park

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 $156
CA $524 total
includes taxes & fees
Mar 2 - Mar 3
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

The Historic Hideaway

The Historic Hideaway
Avon
5.4 out of 10, (3 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 $100
CA $368 total
includes taxes & fees
Feb 23 - Feb 24
The Historic Hideaway

Relaxing Retreat w/Sweet Yard!

Relaxing Retreat w/Sweet Yard!
Bloomfield
The price is CA $172
CA $927 total
includes taxes & fees
Feb 24 - Feb 25
Relaxing Retreat w/Sweet Yard!

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is CA $156
CA $521 total
includes taxes & fees
Feb 19 - Feb 20
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

Find out more about Winchester

Winchester Apartments information

Number of reviews
90
Accommodation
62 Apartments
Lowest Price
CA $252
Highest Price
CA $927

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can search through 6 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?
Here are some of the top apartments in the area to choose from: The Birdsong Apt. | Game Room & Fire Pit: Situated in Winsted, 2.3 mi/3.7 km from the heart of Winchester. West Hartford Center 1st floor: Located 22.7 mi/36.5 km away in West Hartford. Amenities include free WiFi. Access to onsite laundry facilities is available on site. West Hartford Center Apartment: Located in West Hartford, 22.7 mi/36.5 km away. Includes private balconies, jetted bathtubs, and Smart TVs. Onsite laundry facilities and a hot tub are on site. The Historic Hideaway: Located 17 mi/27.3 km away in Avon. Private patios and sofa beds are included. Access to onsite laundry facilities is available on site. Peaceful Meadow Retreat: Located in Granby, 15.6 mi/25.2 km from Winchester. Includes private patios and Smart TVs. Access to onsite laundry facilities is available on site.
How many apartments can I expect to find in Winchester?
Expedia has 6 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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