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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 30 Apartments in Winchester with updated reviews, rates, and availability.

Cozy 2-bedroom Unit with private backyard
Fridge, microwave, oven, stovetop

Cozy 2-bedroom Unit with private backyard

10.0 out of 10, Exceptional, (21)
"Small but very clean and had everything we needed for our stay "
Cozy 2-bedroom Unit with private backyard
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Exterior

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (8)
"The place was very comfortable and in a great location. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
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, (30)
"Great property with great view, cute suite with everything we needed for a short stay while getting our daughter settled back in at Amherst College. Enjoyed a nice dinner nearby at Blue Rock Shelburne Falls, a little shopping and coffee at Mocha mayas and Shelburne Falls Coffee Roasters. My husband did a little fly fishing just off the property in the Deerfield River. Thank you!"
Private Suite with a Sweet View. Spacious, close to town, dog friendly
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 1,130 total
includes taxes & fees
24 Mar - 25 Mar
Lake Whitingham & Mount Snow Area Village Apartment
Sweet suite in Montague near the canal and downtown Turners Falls.
1 bedroom, iron/ironing board, travel crib, WiFi

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.
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
Riverfront 2 Bedroom Unit 2
Property grounds

Riverfront 2 Bedroom Unit 2

9.8 out of 10, Exceptional, (16)
"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, (13)
"Very cozy basement apartment overlooking the water. Quiet road. Owner was very pleasant and accommodating."
Lakefront Orange Vacation Rental - Pet Friendly!
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.

Entire private apartment suite in home with own entrance, views and private gym.
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

The price is SAR 281
SAR 729 total
includes taxes & fees
27 Mar - 28 Mar
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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, (14)
"Great experience. "
Updated Vintage Apartment < 1/2 Mi to Main St
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Property grounds

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

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

9.6 out of 10, Exceptional, (12)
"Great location, a short walk to downtown Peterborough.the rental had everything i needed. Ben and Maryann were helpful with any questions i had. I would stay here again if in the area."
The price is SAR 263
SAR 570 total
includes taxes & fees
24 Mar - 25 Mar
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
Exterior

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

9.6 out of 10, Exceptional, (4)
"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!
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
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)
"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
Charming Ground-Floor 2/3 bedroom apartment in Shelburne Falls, MA
Living area

Charming Ground-Floor 2/3 bedroom apartment in Shelburne Falls, MA

2.0 star property
The price is SAR 653
SAR 1,099 total
includes taxes & fees
24 Mar - 25 Mar
Charming Ground-Floor 2/3 bedroom apartment in Shelburne Falls, MA
Updated Vintage Apartment < 1/2 Mi to Main St
Apartment (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Updated Vintage Apartment < 1/2 Mi to Main St

3.0 star property
Updated Vintage Apartment < 1/2 Mi to Main St
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Interior

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

3.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Experience New Hampshire Country Life—Your Peaceful Escape Awaits
1 bedroom, desk, iron/ironing board, free WiFi

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
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

The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (45)
"The Jelly Mill is a lovely, welcoming cottage in the S. VT town of Guilford, nestled in the hills below the bigger town of Brattleboro. The location feels 'out of the way' - no big roads (or even paved roads), stores, 'hustle or bustle' anywhere close by - but Brattleboro has all that stuff and is only 20-30 minutes away. For 'last minute' items a charming, smaller grocery / sandwich shop is closer by. The property itself is very clean, with an up to date kitchen and glitch-free speedy Wi-Fi...
The Jelly Mill-A River Retreat
Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Online info was accurate. Nice spot to rent with family."
The price is SAR 1,125
SAR 1,950 total
includes taxes & fees
3 Apr - 4 Apr
Cozy Home Near Downtown, Shops, and Restaurants.
Riverfront 2 Bedroom Unit 2
Property grounds

Riverfront 2 Bedroom Unit 2

9.8 out of 10, Exceptional, (16)
"We had a lovely time in central Mass"
Riverfront 2 Bedroom Unit 2
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?
Here are some of the top 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. Stylish new 2 bedroom property in enchanting Shelburne Falls Village.: 21 mi/33.9 km away in Shelburne Falls. Amenities include Smart TVs. Riverfront 2 Bedroom Unit 2: It’s situated in Montague, 14.5 mi/23.3 km from Winchester.
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. Ashuelot River and Barden State Wildlife Management Area are a couple of lovely local spots to get outside and enjoy nature. New England Sweetwater Farm & Distillery and Pisgah State Park are other places to visit while you’re in town.