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Compare 25 Apartments in Winchester with updated reviews, rates, and availability.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

9.6 out of 10, Exceptional, (11)
"I stayed a few nights for a snowboarding trip for my birthday with my partner. Wonderful food spots bearby. The location was very clean, will return 10p percent."
The price is AED 257
AED 558 total
includes taxes & fees
4 Mar - 5 Mar
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

3.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!

The Covey House Retreat with InfraRed Sauna

10.0 out of 10, Exceptional, (3)
"We had an amazing stay, your place is awesome!"
The Covey House Retreat with InfraRed Sauna

Lake Whitingham & Mount Snow Area Village Garden Apartment 2 BR, AC & WiFi

2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
Lake Whitingham & Mount Snow Area Village Garden Apartment 2 BR, AC & WiFi

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (11)
"Great host communication, everything we needed, unexpected extras (like dog treats), and a beautiful view. Would gladly stay again!"
Lakefront Orange Vacation Rental - Pet Friendly!

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

2.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!

Updated Vintage Apartment < 1/2 Mi to Main St

10.0 out of 10, Exceptional, (11)
"This property was just as expected and Close to top notch restaurants. Kitchen was well equipped and I was able to bake a few casseroles for our family we were visiting.The area was nice and quiet. Will visit again."
Updated Vintage Apartment < 1/2 Mi to Main St

Entire private apartment suite in home with own entrance, views and private gym.

The price is AED 1,010
AED 1,467 total
includes taxes & fees
9 Feb - 10 Feb
Entire private apartment suite in home with own entrance, views and private gym.

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (6)
"From this location easily walked into Shelburne Falls village, enjoyed lunch by the Fallls and got groceries at Buckland. Great hiking trails in the area. Trailhead 5 minute drive away"
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

Spacious 3/4-bedroom apt 5 minutes walk to charming Shelburne Falls center.

2.0 star property
Spacious 3/4-bedroom apt 5 minutes walk to charming Shelburne Falls center.

'Red Sweetheart Barn Studio' w/ Mtn & River Views!

10.0 out of 10, Exceptional, (3)
"It was cozy and beautiful and very inviting loved every part"
'Red Sweetheart Barn Studio' w/ Mtn & River Views!

HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley

10.0 out of 10, Exceptional, (4)
"We stayed for the weekend and absolutely loved it- it was huge! Warm and inviting- full kitchen and bathroom, crib in the closet for a wee one. It was so clean and smelled good too- great windows and easy furniture. Bed was superb! Would stay again in a heartbeat. "
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley

Quiet Neighborhood, For Bird Lovers

10.0 out of 10, Exceptional, (46)
" My husband and I felt at home at the opening of the door!! The location is beautiful and serene, making relaxation unavoidable! The hostess thought of every little detail! Thank you Manon for a perfectly lovely stay!!"
Quiet Neighborhood, For Bird Lovers

Lovely Greenfield Apartment

2.0 star property
8.0 out of 10, Very Good, (1)
"Very well decorated apartment. The property owner was so helpful and easy to get in touch with"
Lovely Greenfield Apartment

Updated Vintage Apartment < 1/2 Mi to Main St

3.0 star property
Updated Vintage Apartment < 1/2 Mi to Main St

Experience New Hampshire Country Life—Your Peaceful Escape Awaits

9.8 out of 10, Exceptional, (30)
"We had a short stay but the hosts were wonderful and gave us a tour when we arrived. The property is gorgeous. Definitely recommend staying here."
Experience New Hampshire Country Life—Your Peaceful Escape Awaits

Quiet New England neighborhood - Greenfield, Ma. One guest only, 7 nights max.

10.0 out of 10, Exceptional, (5)
"The property was very clean and had everything I would ever need. The landlord was very nice and took care of trash weekly! A perfect stay"
Quiet New England neighborhood - Greenfield, Ma. One guest only, 7 nights max.

Sweet suite in Montague near the canal and downtown Turners Falls.

2.0 star property
9.6 out of 10, Exceptional, (4)
"I had a great stay at Callie’s. The room was comfortable and clean and had all the amenities one needs! "
Sweet suite in Montague near the canal and downtown Turners Falls.

Cozy 1-bedroom apartment in delightful Brattleboro

Cozy 1-bedroom apartment in delightful Brattleboro

'red Sweetheart Barn Studio' w/ Mtn & River Views!

3.0 star property
'red Sweetheart Barn Studio' w/ Mtn & River Views!
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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Other property types in Winchester

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (113)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

6.8 out of 10, (13)
"We enjoyed our stay. AWD is a must for the driveway. The number of security cameras around the property is uncomfortable."
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
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.

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You’ll find 6 hotels and other accommodations in Winchester. Though there aren’t many apartments, we can help you find accommodations with similar amenities. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. You can also search for similar property types like condos, vacation homes, or cottages. Why not take time to appreciate the lakeside during your visit?
How do you know if an apartment is the right choice for you?
An apartment features a kitchen for convenient meals, and often has more space than a traditional hotel room. Apartments are a good option for solo travelers who want to stay in at night and plan out their next day, but also for families wanting the conveniences of home.
What's a favorite apartment for a stay in Winchester?
Below are some of the more popular apartments in the area: Cozy 2-bedroom Unit with private backyard: Located 14.5 mi/23.3 km away in Montague. Free WiFi, private patios, and Smart TVs are included. Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.: It’s situated in Peterborough, 23.2 mi/37.4 km away. Includes free WiFi and Smart TVs.
What will the weather be like when I travel to 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 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.
What are the must-see places to visit in Winchester?
Winchester is known for its lakeside. Pisgah State Park and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. Birch Point and Rhododendron State Park are other places to visit while you’re in town.