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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 34 Apartments in Winchester with updated reviews, rates, and availability.

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
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, (17)
"Property was clean and super close to the downtown square! "
The price is AED 331
AED 638 total
includes taxes & fees
11 Jun - 12 Jun
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
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)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
The price is AED 312
AED 755 total
includes taxes & fees
4 Jun - 5 Jun
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Beautiful Townhouse In Turners Falls!
Fridge, microwave, oven, stovetop

Beautiful Townhouse In Turners Falls!

9.8 out of 10, Exceptional, (134)
"I had a Great Stay, nice place."
Beautiful Townhouse In Turners Falls!
Lakefront Orange Vacation Rental - Pet Friendly!
Outdoor dining

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (16)
"It’s a wonderful place to stay!!"
Lakefront Orange Vacation Rental - Pet Friendly!
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)
"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 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
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 AED 514
AED 1,123 total
includes taxes & fees
14 Jun - 15 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, (1)
"Excellent little cozy cabin perfect for me. Kitchen was well stocked with what I needed for small meals made. Bed and bathroom excellent. Was able to enjoy a woods walk in the nearby town forest. Will be back soon. Wanted to add an extra day and that was accommodated with ease."
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

10.0 out of 10, Exceptional, (16)
"Great experience. "
Updated Vintage Apartment < 1/2 Mi to Main St
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
Riverside Retreat – Cozy 2-Story Getaway!
Fridge, microwave, oven, stovetop

Riverside Retreat – Cozy 2-Story Getaway!

10.0 out of 10, Exceptional, (24)
"Small but very clean and had everything we needed for our stay "
Riverside Retreat – Cozy 2-Story Getaway!
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 AED 358
AED 488 total
includes taxes & fees
4 Jun - 5 Jun
Welcome to "Down Under" the Hall's House A peaceful escape in Southern Vermont.
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
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
Deck, Mountain Views: Colorful Retreat in Vernon!
Terrace/patio

Deck, Mountain Views: Colorful Retreat in Vernon!

Deck, Mountain Views: Colorful Retreat in Vernon!
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 AED 1,010
AED 1,463 total
includes taxes & fees
16 Jun - 17 Jun
Entire private apartment suite in home with own entrance, views and private gym.
The Covey House Retreat with InfraRed Sauna
Outdoor dining

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
Deck, Mountain Views: Colorful Retreat in Vernon!
Interior

Deck, Mountain Views: Colorful Retreat in Vernon!

3.0 star property
Deck, Mountain Views: Colorful Retreat in Vernon!
Lakefront Orange Vacation Rental - Pet Friendly!
Interior

Lakefront Orange Vacation Rental - Pet Friendly!

3.0 star property
Lakefront Orange Vacation Rental - Pet Friendly!
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. Cozy apt in beautiful secluded spot 15 mins from Mt Snow: Located 22.9 mi/36.9 km away in East Dover. Lakefront Orange Vacation Rental - Pet Friendly!: It’s situated in Orange, 12.1 mi/19.4 km away. Includes fireplaces. Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.: 23.2 mi/37.4 km away in Peterborough. Free WiFi and Smart TVs are included. 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. Birch Point and Cass Pond are a couple of lovely local spots to get outside and enjoy nature. Winchester Speedpark and Pisgah State Park are other places to visit while you’re in town.