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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Apartments in Winchester

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 413
SAR 741 total
includes taxes & fees
5 Aug - 6 Aug
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Riverside Retreat – Cozy 2-Story Getaway!
Fridge, microwave, oven, stovetop

Riverside Retreat – Cozy 2-Story Getaway!

9.8 out of 10, Exceptional, (27)
"Interior amazing. Exterior could use some attention"
Riverside Retreat – Cozy 2-Story Getaway!
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 771 total
includes taxes & fees
31 Jul - 1 Aug
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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, (3)
"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!
Lakefront Orange Vacation Rental - Pet Friendly!
Outdoor dining

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (21)
"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!
Walk to Trails: Artsy Mtn-view Getaway in Vernon!
Apartment (1 Bedroom) | Interior

Walk to Trails: Artsy Mtn-view Getaway in Vernon!

3.0 star property
Walk to Trails: Artsy Mtn-view Getaway in Vernon!
Walk to Trails: Artsy Mtn-View Getaway in Vernon!
Fridge, stovetop, coffee/tea maker, toaster

Walk to Trails: Artsy Mtn-View Getaway in Vernon!

10.0 out of 10, Exceptional, (1)
"Needed to be in the VT/NH area for a funeral. Was able to get around to locations and have a nice place to stay between. Was able to get to things in MA/VT and NH easily. Loved the cute kitchen area. Bed was very comfortable. "
Walk to Trails: Artsy Mtn-View Getaway in Vernon!
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, (32)
"Great space. Lots of room for us and very clean and comfortable."
Private Suite with a Sweet View. Spacious, close to town, dog friendly
Ground floor 2/3 bed apartment
Property grounds

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. "
The price is SAR 724
SAR 1,106 total
includes taxes & fees
24 Jul - 25 Jul
Ground floor 2/3 bed apartment
Beautiful Townhouse In Turners Falls!
Property grounds

Beautiful Townhouse In Turners Falls!

9.8 out of 10, Exceptional, (136)
"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!
'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!
Lake Whitingham & Mount Snow Area Village Apartment
Property grounds

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 1,155 total
includes taxes & fees
22 Jul - 23 Jul
Lake Whitingham & Mount Snow Area Village Apartment
Charming 2-bedroom apartment in Keene with WiFi and AC
Smart TV

Charming 2-bedroom apartment in Keene with WiFi and AC

10.0 out of 10, Exceptional, (1)
"The apartment was very clean and spacious."
The price is SAR 1,650
SAR 2,035 total
includes taxes & fees
5 Aug - 6 Aug
Charming 2-bedroom apartment in Keene with WiFi and AC
Riverfront 2 Bedroom Unit 2
Microwave, oven, stovetop

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!
Apartment (1 Bedroom) | Interior

Lakefront Orange Vacation Rental - Pet Friendly!

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

Deck, Mountain Views: Colorful Retreat in Vernon!

10.0 out of 10, Exceptional, (1)
"comfortable and quiet... would stay again! (you must be comfortable with stairs though)"
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, (5)
"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
Sweet Suite in Montague near Colleges and Downtown Turners Falls Great Falls.
Interior

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

2.0 star property
9.6 out of 10, Exceptional, (7)
"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
Property grounds

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
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
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Nice property; clean and recently refurbished. Very friendly staff."
Scot 2-night trip
Posted 1 day ago
Hampton Inn Brattleboro

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: Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.: Situated in Peterborough, 23.2 mi/37.4 km from the heart of Winchester. Includes free WiFi and Smart TVs. Lakefront Orange Vacation Rental - Pet Friendly!: Located 12.1 mi/19.4 km away in Orange. Amenities include fireplaces. Riverside Retreat – Cozy 2-Story Getaway!: It's situated in Montague, 14.5 mi/23.3 km away. Includes free WiFi, private patios, and Smart TVs. Cozy apt in beautiful secluded spot 15 mins from Mt Snow: It's situated in East Dover, 22.9 mi/36.9 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. Richmond Wildlife Manangement Area and Rhododendron State Park 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.