Search Winchester Cottages

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Cottages in Winchester

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (35)
"Clean stunning views amazing host "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Private Island - Largest Fresh Water Reservoir in Mass....
Interior

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....
Idillic summer getaway in Litchfield Hills, CT.
Property grounds

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"Great spot close to Limerock Raceway - private, cute, and a perfect spot to stay! The owners are so nice and accommodating - I couldn’t say nicer things about this place and will be back!"
Idillic summer getaway in Litchfield Hills, CT.
Summer Lake Cottage, private beach, Berkshire Hills, small village
Exterior

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (81)
"Amazing cabin, thank you for a beautiful stay! We came in for a wedding and this was a great location to where the wedding was held. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Cozy 2-bedroom Cottage with Access to Bantam Lake
Property grounds

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (18)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Property grounds

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (40)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
East Otis Vacation Rental w/ Private Deck & BBQ!
Desk, internet, bed sheets

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (10)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Lakefront Tranquility/Fishermans Delight
Interior

Lakefront Tranquility/Fishermans Delight

9.8 out of 10, Exceptional, (19)
"Great cabin very relaxing"
Lakefront Tranquility/Fishermans Delight
Charming, private 2-bedroom cottage on classic New England farm in Washington CT
Exterior

Charming, private 2-bedroom cottage on classic New England farm in Washington CT

10.0 out of 10, Exceptional, (4)
"Four of us were in town for a family party and really enjoyed our stay at the cottage. It’s peaceful, cozy, very well appointed, and wonderfully decorated. We also enjoyed a visit with the goats! "
Charming, private 2-bedroom cottage on classic New England farm in Washington CT
Guest Cottage on Country Estate
Outdoor dining

Guest Cottage on Country Estate

9.2 out of 10, Wonderful, (41)
"the location and size of cottage were just what we were looking for."
Guest Cottage on Country Estate
Two Bedroom Cottage Close To Town
Fridge, microwave, oven, stovetop

Two Bedroom Cottage Close To Town

9.2 out of 10, Wonderful, (23)
"The house had everything we needed. The full kitchen served us well, the beds were comfortable, and the showers were great!"
Two Bedroom Cottage Close To Town
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
House (2 Bedrooms) | Interior

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (9)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
$369 nightly
The price is $412
Aug 17 - Aug 18
Total includes taxes and fees
The Blue Elm - A Historic Berkshire Cottage
Westfield Vacation Rental w/ Porch, Pets Welcome!
Interior

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Exterior

Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

9.4 out of 10, Exceptional, (10)
"The owners freshly love this place"
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Quiet rustic cottage with shared lake access
Fridge, microwave, oven, stovetop

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (109)
"Lovely lake house at the end of a long private road, perfect for a quiet getaway, close to all kinds of hiking and other natural attractions. Our hosts were super friendly and responsive. Highly recommended."
Quiet rustic cottage with shared lake access
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Interior

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.4 out of 10, Exceptional, (13)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Property grounds

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (6)
"Really enjoyed this cute little cottage right on the lake. Brought our 3 year old to visit family. Nice bedrooms. Gorgeous deck. Really good communication from the owner as far as directions and such. Would go back for sure. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Modern Terryville Cottage w/ Deck & Lake View!
Interior

Modern Terryville Cottage w/ Deck & Lake View!

3.0 star property
10.0 out of 10, Exceptional, (1)
Modern Terryville Cottage w/ Deck & Lake View!
Perfect Vacation Get Away - Historical New Marlborough
Property grounds

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (55)
"Lovely place!"
Perfect Vacation Get Away - Historical New Marlborough
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"Historical inn with a great welcoming staff. "
Paul 3-night trip
Posted 20 hours ago
Simsbury 1820 House