Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Winchester vacation rentals

Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (18 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is ￥15,336
￥29,864 total
includes taxes & fees
Mar 11 - Mar 12
Peaceful Meadow Retreat
Exterior

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is ￥14,248
￥53,508 total
includes taxes & fees
Mar 12 - Mar 13
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Interior

#31 - Downtown Terryville- 1 Br

#31 - Downtown Terryville- 1 Br
Plymouth
10.0 out of 10, Exceptional, (1 review)
"In convenient safe area. Os is easy to contact"
United States
Gina P.
The price is ￥15,628
￥37,863 total
includes taxes & fees
Mar 14 - Mar 15
#31 - Downtown Terryville- 1 Br
Property grounds

Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.0 out of 10, (3 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is ￥12,149
￥41,566 total
includes taxes & fees
Apr 7 - Apr 8
Sun Filled Lake House Living
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ￥16,756
￥101,473 total
includes taxes & fees
Mar 11 - Mar 12
CT Gate House Goshen CT, Gate House Goshen CT
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 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is ￥28,400
￥52,534 total
includes taxes & fees
Mar 22 - Mar 23
Big farmhouse in the foothills of the Berkshires
Interior

Cozy & Serene Cabin with Fireplace, Ski Nearby!

Cozy & Serene Cabin with Fireplace, Ski Nearby!
Bethlehem
9.8 out of 10, Exceptional, (40 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
The price is ￥31,556
￥66,346 total
includes taxes & fees
Mar 11 - Mar 12
Cozy & Serene Cabin with Fireplace, Ski Nearby!
Property grounds

River Overlook - Check the view from your deck!

River Overlook - Check the view from your deck!
Collinsville
10.0 out of 10, Exceptional, (23 reviews)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
The price is ￥21,158
￥42,201 total
includes taxes & fees
Mar 11 - Mar 12
River Overlook - Check the view from your deck!
Exterior

Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is ￥20,377
￥62,974 total
includes taxes & fees
Mar 11 - Mar 12
Cozy Modern Farmhouse Private Apt - 3 Beds
Dining

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is ￥20,709
￥63,535 total
includes taxes & fees
Mar 11 - Mar 12
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Interior

The Historic Hideaway

The Historic Hideaway
Avon
5.4 out of 10, (3 reviews)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is ￥12,149
￥42,986 total
includes taxes & fees
Mar 16 - Mar 17
The Historic Hideaway
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is ￥41,181
￥62,584 total
includes taxes & fees
Mar 11 - Mar 12
Litchfield Retreat, Wineries, Foliage & Skiing
Interior

Pristine, Walkable downtown, Entire 2 Bedroom apartment

Pristine, Walkable downtown, Entire 2 Bedroom apartment
Torrington
10.0 out of 10, Exceptional, (16 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
The price is ￥25,245
￥43,863 total
includes taxes & fees
Mar 11 - Mar 12
Pristine, Walkable downtown, Entire 2 Bedroom apartment
Interior

#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Plainville
8.4 out of 10, Very Good, (12 reviews)
"Great place ! Quiet and safe place! We will be back! "
United States
Aubrey C.
The price is ￥21,931
￥50,308 total
includes taxes & fees
Mar 11 - Mar 12
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
1 bedroom, iron/ironing board, free WiFi, bed sheets

#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
9.0 out of 10, Wonderful, (2 reviews)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
The price is ￥13,344
￥30,342 total
includes taxes & fees
Mar 12 - Mar 13
#2 *Beautiful 1 BR Apartment - Central CT*
Dining

Whispering Estate Guest House - Countryside Getaway

Whispering Estate Guest House - Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is ￥85,201
￥138,767 total
includes taxes & fees
Mar 11 - Mar 12
Whispering Estate Guest House - Countryside Getaway
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is ￥63,112
￥107,330 total
includes taxes & fees
Mar 11 - Mar 12
Guesthouse Cabin vacation rentals in Berkshire County
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is ￥41,338
￥87,722 total
includes taxes & fees
Mar 11 - Mar 12
Treetop Hideaway in Tyringham
Interior

Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT

Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Bloomfield
The price is ￥76,018
￥200,233 total
includes taxes & fees
Mar 12 - Mar 13
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Interior

Relaxing Retreat w/Sweet Yard!

Relaxing Retreat w/Sweet Yard!
Bloomfield
The price is ￥19,880
￥106,012 total
includes taxes & fees
Mar 16 - Mar 17
Relaxing Retreat w/Sweet Yard!
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

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Beautiful property and complimentary breakfast on the go made our stay memorable, looking to coming back in the future."
Nabonita 1-night trip
Posted 8 hours ago
Avon Old Farms Hotel

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Are there vacation rentals in Winchester?

Yes, there are vacation rentals in Winchester close to Laurel Lanes, or you can choose a more remote option if you're looking for extra privacy while you relax.

What are some of the best vacation rentals that Winchester has to offer?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This vacation home rental near Winchester offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Winchester?

Expedia has 7 vacation rentals for your stay in Winchester.

What’s there to see and do in Winchester?

Highland Lake and Walker Field are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Laurel Lanes. While here, Burr Pond State Park and The Marina at Highland Lake are other places worth a visit.

What’s a vacation rental in Winchester like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Winchester. Vacation rentals offer extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family trips.