Photo by Donny Campos

Search Cottages in Winchester

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 17 Cottages in Winchester with updated reviews, rates, and availability.

Interior
Historic Home w/ Modern Updates on < 4 Acres
3.5 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
Interior
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Interior
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.5 star property
10.0 out of 10, Exceptional, (1)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Interior
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Interior
Cozy Falls Brook Cabin: Hike & Swim On-site!
3.5 star property
Cozy Falls Brook Cabin: Hike & Swim On-site!
Interior
Jacksonville Cabin w/ Wraparound Deck & Views
3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Interior
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Interior
Cozy 'green Mountain Chalet' in Putney Town
3.0 star property
Cozy 'green Mountain Chalet' in Putney Town
Interior
Charming Jaffrey Cottage w/ Deck & Grill!
3.5 star property
Charming Jaffrey Cottage w/ Deck & Grill!
Interior
Timeless Red Sox Retreat w/ Scenic Mountain Views!
3.0 star property
Timeless Red Sox Retreat w/ Scenic Mountain Views!
Interior
West Dover Vacation Rental ~ 6 Mi to Resort!
3.0 star property
West Dover Vacation Rental ~ 6 Mi to Resort!
View from property
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!
3.0 star property
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!
Interior
Marlboro Escape: 9 Mi to Mount Snow Resort!
3.0 star property
Marlboro Escape: 9 Mi to Mount Snow Resort!
Interior
Cozy Mount Snow Chalet w/ Game Room & Hot Tub
3.5 star property
Cozy Mount Snow Chalet w/ Game Room & Hot Tub
Interior
Charming Putney Home: Porch, Grill & Hiking Trails
3.0 star property
Charming Putney Home: Porch, Grill & Hiking Trails
Don't see what you're looking for?
See all available properties in Winchester
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.

Other property types in Winchester

Winchester Cottages information

Number of reviews
4
Accommodation
17 Cottages
Lowest Price
Highest Price

Recent reviews of Winchester hotels
Expedia verified reviews

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

4/5 Good
"Easy check in & friendly staff. But, neither card worked to unlock our door so had to go back to the front desk. TV remote worked but wouldn't change channel..had 1 channel with old westerns 😒"
A verified traveler stayed at Days Inn by Wyndham Keene NH
Posted 2 days ago
Days Inn by Wyndham Keene NH