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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Apartments in Winchester

Riverfront 2 Bedroom Unit 2
Property grounds

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (19)
"We had a lovely time in central Mass"
Riverfront 2 Bedroom Unit 2
Lakefront Orange Vacation Rental - Pet Friendly!
Outdoor dining

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (17)
"This place was perfect for our stay! It was clean, nicely decorated/designed and had thoughtful touches. The pictures were spot on for what to expect, it was peaceful, and the view was lovely. Crystal was great and check-in/out was easy! We would definitely stay here again."
Lakefront Orange Vacation Rental - Pet Friendly!
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (18)
"Property was clean and super close to the downtown square! "
The price is SAR 371
SAR 688 total
includes taxes & fees
26 Jun - 27 Jun
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Beautiful Townhouse In Turners Falls!
Fridge, microwave, oven, stovetop

Beautiful Townhouse In Turners Falls!

9.8 out of 10, Exceptional, (135)
"A terrific, cozy place, convenient, in a cute neighborhood -- super easy check in --- clear directions --- couldn't ask for anything more."
Beautiful Townhouse In Turners Falls!
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

10.0 out of 10, Exceptional, (2)
"We stayed here for couple of days. We loved it all! The place is lovely, very clean, spacious, big, and very convenient. The price is very reasonable. The property is beautiful overall! It has orchard trees and a lake. It reminded us the Vermont house in the movie Baby Boom. The location is very convenient too. 10 mins of driving to the MT Snow Ski Resort with lots of winter activities , and also 10 mins of driving to town center of West Dover. We walked in town and shopped in the small...
The price is SAR 319
SAR 776 total
includes taxes & fees
30 Jun - 1 Jul
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Ground floor 2/3 bed apartment
Living area

Ground floor 2/3 bed apartment

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great property and location for a visit to Shelburne Falls. "
Ground floor 2/3 bed apartment
Lake Whitingham & Mount Snow Area Village Apartment
Outdoor dining

Lake Whitingham & Mount Snow Area Village Apartment

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."
The price is SAR 525
SAR 1,147 total
includes taxes & fees
24 Jun - 25 Jun
Lake Whitingham & Mount Snow Area Village Apartment
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Property grounds

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Very clean, and comfortable. Small but cozy for a romantic get-away for 2 in Vermont! Decor in French country. Lovely..tres beau!"
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Updated Vintage Apartment < 1/2 Mi to Main St
Fridge, microwave, stovetop, dishwasher

Updated Vintage Apartment < 1/2 Mi to Main St

9.6 out of 10, Exceptional, (17)
"Apartment was very clean, comfortable and had Great location!!!!"
Updated Vintage Apartment < 1/2 Mi to Main St
Riverside Retreat – Cozy 2-Story Getaway!
Fridge, microwave, oven, stovetop

Riverside Retreat – Cozy 2-Story Getaway!

9.8 out of 10, Exceptional, (25)
"Interior amazing. Exterior could use some attention"
Riverside Retreat – Cozy 2-Story Getaway!
Private Suite with a Sweet View. Spacious, close to town, dog friendly
Exterior

Private Suite with a Sweet View. Spacious, close to town, dog friendly

10.0 out of 10, Exceptional, (31)
"Great space. Lots of room for us and very clean and comfortable."
Private Suite with a Sweet View. Spacious, close to town, dog friendly
Welcome to "Down Under" the Hall's House A peaceful escape in Southern Vermont.
Interior

Welcome to "Down Under" the Hall's House A peaceful escape in Southern Vermont.

The price is SAR 450
SAR 594 total
includes taxes & fees
24 Jun - 25 Jun
Welcome to "Down Under" the Hall's House A peaceful escape in Southern Vermont.
Deck, Mountain Views: Colorful Retreat in Vernon!
Terrace/patio

Deck, Mountain Views: Colorful Retreat in Vernon!

Deck, Mountain Views: Colorful Retreat in Vernon!
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
Exterior detail

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

10.0 out of 10, Exceptional, (4)
"This was my second time staying in the barn and I enjoyed it. The property is in a good location and very quiet."
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
Exterior

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

9.8 out of 10, Exceptional, (6)
"We enjoyed a few night springtime stay at this beautiful cabin! The view was wonderful, and the accommodations were very nicely decorated. Some things we would love to see improvement on before staying again: there were no washcloths available in the upstairs bathroom, and no garbage can available in the downstairs one. No tissues to be found in the entire space. The bed was extremely uncomfortable, and the pillows as well. We also found fingernail clippings in the sheets, which was problematic,...
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
Sweet Suite in Montague near Colleges and Downtown Turners Falls Great Falls.
1 bedroom, iron/ironing board, travel crib, WiFi

Sweet Suite in Montague near Colleges and Downtown Turners Falls Great Falls.

2.0 star property
9.6 out of 10, Exceptional, (4)
"My daughter and I were visiting friends and needed a quiet place to decompress after busy days. The Sweet Suite fit the bill! It was clean, comfortable, and quiet."
Sweet Suite in Montague near Colleges and Downtown Turners Falls Great Falls.
Quiet Neighborhood, For Bird Lovers
Fridge, microwave, oven, stovetop

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

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

The price is SAR 929
SAR 1,362 total
includes taxes & fees
24 Jun - 25 Jun
Entire private apartment suite in home with own entrance, views and private gym.
Cozy 1-bedroom apartment in delightful Brattleboro
Fridge, microwave, oven, stovetop

Cozy 1-bedroom apartment in delightful Brattleboro

Cozy 1-bedroom apartment in delightful Brattleboro
Deck, Mountain Views: Colorful Retreat in Vernon!
Apartment (2 Bedrooms) | Interior

Deck, Mountain Views: Colorful Retreat in Vernon!

3.0 star property
Deck, Mountain Views: Colorful Retreat in Vernon!
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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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?
Here are some of the top apartments in the area: Riverfront 2 Bedroom Unit 2: Situated in Montague, 14.5 mi/23.3 km from the heart of Winchester. Lakefront Orange Vacation Rental - Pet Friendly!: Located 12.1 mi/19.4 km away in Orange. Amenities include fireplaces. 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. Cozy apt in beautiful secluded spot 15 mins from Mt Snow: 22.9 mi/36.9 km away in East Dover. Beautiful Townhouse In Turners Falls!: Located in Montague, 14.7 mi/23.7 km from Winchester. Includes laundry facilities and private balconies. Access to onsite laundry facilities is available on site.
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. Rhododendron State Park and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. New England Sweetwater Farm & Distillery and Winchester Speedpark are other places to visit while you're in town.