Search Vacation Homes in Winchester

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Winchester vacation homes

Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
Goshen
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$614 nightly
The price is $629
Dec 14 - Dec 15
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Private kitchen
Home in the Woods

Home in the Woods

Russell
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
United States
Travis H.
$304 nightly
The price is $321
Dec 10 - Dec 11
Total with taxes and fees
Home in the Woods
Property grounds
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

East Granby
8.6 out of 10, Excellent, (4)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
United States
Sgt W.
$394 nightly
The price is $446
Dec 10 - Dec 11
Total with taxes and fees
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Smart TV, fireplace
Sun Filled Lake House Living

Sun Filled Lake House Living

2.0 star property
Avon
6.0 out of 10, (3)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
$237 nightly
The price is $250
Dec 19 - Dec 20
Total with taxes and fees
Sun Filled Lake House Living
Terrace/patio
Charming 1-bedroom in welcoming West Hartford with WiFi, AC

Charming 1-bedroom in welcoming West Hartford with WiFi, AC

West Hartford
$112 nightly
The price is $126
Dec 14 - Dec 15
Total with taxes and fees
Charming 1-bedroom in welcoming West Hartford with WiFi, AC
Property grounds
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Russell
10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
$344 nightly
The price is $364
Dec 10 - Dec 11
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$406 nightly
The price is $454
Dec 10 - Dec 11
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Property grounds
Stylish Townhome | Perfect for Family Gatherings & Events

Stylish Townhome | Perfect for Family Gatherings & Events

2.0 star property
Bloomfield
10.0 out of 10, Exceptional, (4)
"The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family."
United States
Muhammad G.
$607 nightly
The price is $688
Dec 10 - Dec 11
Total with taxes and fees
Stylish Townhome | Perfect for Family Gatherings & Events
Fridge, microwave, oven, stovetop
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville
10.0 out of 10, Exceptional, (61)
"Fabulous location. I can honestly say cleanest VRBO we’ve ever stayed!!"
United States
Jeanmarie G.
$401 nightly
The price is $454
Dec 10 - Dec 11
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Private kitchen
Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing

2.0 star property
Torrington
$318 nightly
The price is $360
Dec 10 - Dec 11
Total with taxes and fees
Litchfield Retreat, Wineries, Foliage & Skiing
Exterior
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

2.0 star property
Goshen
$460 nightly
The price is $522
Dec 15 - Dec 16
Total with taxes and fees
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Fridge, microwave, oven, stovetop
Modern Ranch Retreat in Hudson Valley

Modern Ranch Retreat in Hudson Valley

Millerton
10.0 out of 10, Exceptional, (4)
"Great communication and a fantastic property! The setting is quiet and short walk to downtown Millerton. The Harlem Valley Rail Trail Line is just down the road which offers excellent opportunities for adventures!"
United States
Scott E.
$486 nightly
The price is $550
Dec 17 - Dec 18
Total with taxes and fees
Modern Ranch Retreat in Hudson Valley
Property grounds
Charming 3-bedroom Modern cottage with lakeside views

Charming 3-bedroom Modern cottage with lakeside views

2.0 star property
Hartland
$1,314 nightly
The price is $1,487
Dec 12 - Dec 13
Total with taxes and fees
Charming 3-bedroom Modern cottage with lakeside views
Interior
Group-Friendly Townhouse Stay – Sleeps up to 20

Group-Friendly Townhouse Stay – Sleeps up to 20

Bloomfield
$936 nightly
The price is $1,061
Dec 11 - Dec 12
Total with taxes and fees
Group-Friendly Townhouse Stay – Sleeps up to 20
Interior
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
Bloomfield
9.4 out of 10, Exceptional, (3)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
United States
Joslynn T.
$607 nightly
The price is $688
Dec 11 - Dec 12
Total with taxes and fees
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Fridge, microwave, oven, stovetop
Premium 3-Story Townhome | Perfect for Large Groups

Premium 3-Story Townhome | Perfect for Large Groups

2.0 star property
Bloomfield
9.2 out of 10, Wonderful, (5)
"Great stay. "
United States
Le Dung H.
$607 nightly
The price is $688
Dec 11 - Dec 12
Total with taxes and fees
Premium 3-Story Townhome | Perfect for Large Groups
Fridge, microwave, oven, stovetop
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT

Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT

Bloomfield
$915 nightly
The price is $1,040
Dec 11 - Dec 12
Total with taxes and fees
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
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

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Clean room, staff were friendly, helpful and kind. Quiet even with planes landing right next door. Can't compliment this place enough."
Christine 1-night trip
Posted 22 hours ago
Sheraton Hartford Hotel at Bradley Airport

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
271
Accommodation
215 Vacation Homes
Lowest Price
$250
Highest Price
$1,487

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