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Check prices for these dates

Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov
In one month
28 Nov - 30 Nov
In two months
26 Dec - 28 Dec

Apartments in Winchester

Fridge, microwave, oven, stovetop
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
9.8 out of 10, Exceptional, (27)
"My stay was what I wanted – quiet and time to study and pray. The town has many beautiful brick buildings and quaint shops for shopping. I thoroughly enjoyed my stay."
United States
Betty D.
The price is AED 281
AED 584 total
includes taxes & fees
3 Nov - 4 Nov
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Property grounds
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
10.0 out of 10, Exceptional, (4)
"Catherine contacted me immediately that the studio I had rented was not available but that we could have the adjacent house instead. She moved heaven and earth to make sure we had a king bed ( which is what we wanted). She was very attentive and accommodating. "
United States
Wendy C.
The price is AED 312
AED 755 total
includes taxes & fees
31 Oct - 1 Nov
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment
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."
United States
Anicia K.
The price is AED 514
AED 1,115 total
includes taxes & fees
31 Oct - 1 Nov
Lake Whitingham & Mount Snow Area Village Apartment
Exterior detail
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
The price is AED 238
AED 762 total
includes taxes & fees
2 Nov - 3 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior
Terrific 3-bedroom unit in charming Leverett with AC
Terrific 3-bedroom unit in charming Leverett with AC
The price is AED 735
AED 1,621 total
includes taxes & fees
3 Nov - 4 Nov
Terrific 3-bedroom unit in charming Leverett with AC
Living area
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Rose wisteria 4 guests 2 bedrooms-full+queen beds
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Best value in New England! Staff is supportive and site is super clean. Decor is nice. Comfy beds. Subpar breakfast but who cares?! Free coffee, and the food is a bonus... and again, you can't beat the value!"
Travis 1-night trip
Posted 3 days ago
Keene Elm City Hotel, an Ascend Collection Hotel

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: Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires: Located 16.6 mi/26.7 km away in Greenfield. 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. Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.: It's located in Peterborough, 23.2 mi/37.4 km from Winchester. 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. Rhododendron State Park and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. Pisgah State Park and New England Sweetwater Farm & Distillery are other places to visit while you're in town.