Search Vacation Homes in Winchester

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Homes in Winchester

Private Room/Sunny/Clean/Peace/SelfCheckIn
Fireplace

Private Room/Sunny/Clean/Peace/SelfCheckIn

2.0 star property
10.0 out of 10, Exceptional, (1)
"We enjoyed our stay, would definitely highly recommend "
$165 nightly
The price is $187
Oct 5 - Oct 6
Total with taxes and fees
Private Room/Sunny/Clean/Peace/SelfCheckIn
CT Gate House Goshen CT, Gate House Goshen CT
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
10.0 out of 10, Exceptional, (6)
"Wonderful stay. It really is a gate house. The property is beautiful and the house is spacious. If I was eloquent,I could go on and on... "
$620 nightly
The price is $635
Oct 5 - Oct 6
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Sun Filled Lake House Living
Outdoor dining

Sun Filled Lake House Living

2.0 star property
8.0 out of 10, Very Good, (2)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
$265 nightly
The price is $283
Oct 5 - Oct 6
Total with taxes and fees
Sun Filled Lake House Living
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
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!! "
$471 nightly
The price is $535
Oct 5 - Oct 6
Total with taxes and fees
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
The Sun Filled Cozy Creamery
TV

The Sun Filled Cozy Creamery

8.8 out of 10, Excellent, (21)
"Nice,cozy and a reasonable rate."
$261 nightly
The price is $279
Oct 4 - Oct 5
Total with taxes and fees
The Sun Filled Cozy Creamery
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford
Fridge, microwave, oven, stovetop

Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

9.2 out of 10, Wonderful, (7)
"Beautiful new spacious property in a great safe neighborhood. Very nice for groups. Common Living space s conducive for gathering. Property still under construction as there were other homes still being built. Near busy street but monimal noise. Would stay again."
$479 nightly
The price is $544
Oct 5 - Oct 6
Total with taxes and fees
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford
Home in the Woods
Private kitchen

Home in the Woods

10.0 out of 10, Exceptional, (3)
"Jessica's spot is adorable and tidy, at the end of a quiet, shady lane, with lots of peace and privacy. It was a hot, muggy weekend but there were 2 window units and extra fans to keep us comfortable. The house is well-appointed—we had a busy schedule and were sad we didn't have a chance to use the lovely outdoor fire pit area. Good communication after a minor mixup. Would definitely stay again!"
$295 nightly
The price is $312
Oct 31 - Nov 1
Total with taxes and fees
Home in the Woods
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Property grounds

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

10.0 out of 10, Exceptional, (2)
"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!"
$434 nightly
The price is $493
Oct 4 - Oct 5
Total with taxes and fees
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
KING BED, Affordable Classic Bristol Home Sleep 8+
Fridge, microwave, oven, stovetop

KING BED, Affordable Classic Bristol Home Sleep 8+

$230 nightly
The price is $261
Oct 16 - Oct 17
Total with taxes and fees
KING BED, Affordable Classic Bristol Home Sleep 8+
The Jefferson Guest House, Spacious, Special Views
Interior

The Jefferson Guest House, Spacious, Special Views

10.0 out of 10, Exceptional, (7)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
$329 nightly
The price is $329
Oct 12 - Oct 13
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
Tranquil Litchfield Connecticut Retreat".
Property grounds

Tranquil Litchfield Connecticut Retreat".

9.4 out of 10, Exceptional, (17)
"Good communication from the host"
$284 nightly
The price is $322
Oct 8 - Oct 9
Total with taxes and fees
Tranquil Litchfield Connecticut Retreat".
Whispering Estate Guest House - A Romantic Countryside Getaway
Exterior detail

Whispering Estate Guest House - A Romantic Countryside Getaway

10.0 out of 10, Exceptional, (3)
"Beautiful property and great location. A true retreat. "
$941 nightly
The price is $1,072
Oct 9 - Oct 10
Total with taxes and fees
Whispering Estate Guest House - A Romantic Countryside Getaway
Big farmhouse in the foothills of the Berkshires
Property grounds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (140)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
$338 nightly
The price is $357
Oct 5 - Oct 6
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
$450 nightly
The price is $503
Oct 13 - Oct 14
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Charming 3-bedroom Modern cottage with lakeside views
Property grounds

Charming 3-bedroom Modern cottage with lakeside views

2.0 star property
$1,314 nightly
The price is $1,487
Oct 6 - Oct 7
Total with taxes and fees
Charming 3-bedroom Modern cottage with lakeside views
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (61)
"There is a lot of fun things to do close by. The house was spotless and it was nice to relax on the sofa or outside patio and look at the river. "
$433 nightly
The price is $491
Oct 13 - Oct 14
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Fridge, microwave, oven, stovetop

Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT

$1,087 nightly
The price is $1,230
Oct 5 - Oct 6
Total with taxes and fees
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Stylish Townhome | Perfect for Family Gatherings & Events
Property grounds

Stylish Townhome | Perfect for Family Gatherings & Events

2.0 star property
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."
$473 nightly
The price is $537
Oct 7 - Oct 8
Total with taxes and fees
Stylish Townhome | Perfect for Family Gatherings & Events
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

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

10/10 Excellent
"The staff was welcoming and friendly. The clerk noticed that I had booked a handicap room, which I was unaware of, and upgraded me to a regular room without a problem. This location is excellent as it is right off the interstate, and easy access to shops nearby."
Stephen 4-night trip
Posted 2 days ago
Extended Stay America Suites Hartford Farmington

Find out more about Winchester

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
286
Accommodation
227 Vacation Homes
Lowest Price
$187
Highest Price
$1,487

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