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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
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21 Rab. I - 23 Rab. I
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Compare 25 Apartments in Winchester with updated reviews, rates, and availability.

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

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 281
SAR 590 total
includes taxes & fees
26 Feb - 27 Feb
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Exterior

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

3.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
The Covey House Retreat with InfraRed Sauna
Room

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
Lake Whitingham & Mount Snow Area Village Apartment
Living Room

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 1,134 total
includes taxes & fees
25 Feb - 26 Feb
Lake Whitingham & Mount Snow Area Village Apartment
Lakefront Orange Vacation Rental - Pet Friendly!
Orange Vacation Rental | 1BR | 1BA | 902 Sq Ft | Access Only By Stairs

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (12)
"Very cozy basement apartment overlooking the water. Quiet road. Owner was very pleasant and accommodating."
Lakefront Orange Vacation Rental - Pet Friendly!
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Vernon Vacation Rental | Studio | 1BA | Steps Required | 280 Sq Ft

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

2.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Updated Vintage Apartment < 1/2 Mi to Main St
Keene Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Steps Required for Entry

Updated Vintage Apartment < 1/2 Mi to Main St

10.0 out of 10, Exceptional, (12)
"We enjoyed our long weekend visit to Keene, NH and appreciated Hidden Gem. It was great to have such a well equipped kitchen for cooking together with fresh local foods from the nearby Monadnock Co-op. Hidden Gem was very clean and comfortable. We had 11 inches of snow overnight and the porch steps, sidewalk and driveway were cleared for us early so we could make our plane on time. Our host Sarah was helpful with any questions and needs. We would love to stay again when our travels take us back...
Updated Vintage Apartment < 1/2 Mi to Main St
Entire private apartment suite in home with own entrance, views and private gym.
Guest suite entrance and patio area with outdoor grill.

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

The price is SAR 1,031
SAR 1,497 total
includes taxes & fees
25 Feb - 26 Feb
Entire private apartment suite in home with own entrance, views and private gym.
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Interior

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (6)
"We stayed over the long weekend and went skiing at Berkshire East (15 minutes away). The house was very clean and comfortable. It was the right size for our family of 4. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Spacious 3/4-bedroom apt 5 minutes walk to charming Shelburne Falls center.
Room

Spacious 3/4-bedroom apt 5 minutes walk to charming Shelburne Falls center.

2.0 star property
Spacious 3/4-bedroom apt 5 minutes walk to charming Shelburne Falls center.
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
Westminster Vacation Rental | Studio | 1BA | Stairs Required | 500 Sq Ft

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

10.0 out of 10, Exceptional, (3)
"It was cozy and beautiful and very inviting loved every part"
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
Living area

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
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
Living area

Updated Vintage Apartment < 1/2 Mi to Main St

3.0 star property
Updated Vintage Apartment < 1/2 Mi to Main St
Experience New Hampshire Country Life—Your Peaceful Escape Awaits
Living area

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
Sweet suite in Montague near the canal and downtown Turners Falls.
Room

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.
Cozy 1-bedroom apartment in delightful Brattleboro
Living area

Cozy 1-bedroom apartment in delightful Brattleboro

Cozy 1-bedroom apartment in delightful Brattleboro
'red Sweetheart Barn Studio' w/ Mtn & River Views!
View from property

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

3.0 star property
'red Sweetheart Barn Studio' w/ Mtn & River Views!
Relax peacefully in Gardner Ma, near Mt Wachusett
Private kitchen

Relax peacefully in Gardner Ma, near Mt Wachusett

Relax peacefully in Gardner Ma, near Mt Wachusett
The Pines Cabin | New Tiny Home Near Mt Snow!

The Pines Cabin | New Tiny Home Near Mt Snow!

The Pines Cabin | New Tiny Home Near Mt Snow!
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

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (45)
"A great little cabin close to Mt. Snow. Accurate description. Fire place didn’t work. Would stay here again. "
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (14)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Winter wonderland!

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (113)
"Beautiful and peaceful, great house for a winter getaway with the family. We loved the yard and location. Grab your groceries on the way up, and enjoy the amazing house with your crew, (And dog too) "
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
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: Situated in Montague, 14.5 mi/23.3 km from the heart of Winchester. Includes free WiFi, private patios, and Smart TVs. Lakefront Orange Vacation Rental - Pet Friendly!: Located 12.1 mi/19.4 km away in Orange. Amenities include fireplaces. Beautiful Townhouse In Turners Falls!: It’s situated in Turners Falls, 14.7 mi/23.7 km away. Includes laundry facilities and private balconies. 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. Pisgah State Park and Rhododendron State Park are a couple of lovely local spots to get outside and enjoy nature. Ashuelot River and New England Sweetwater Farm & Distillery are other places to visit while you’re in town.