A snow-covered landscape with a stone bridge, a small tower, and a forested hill.

Holiday Rentals in Litchfield County

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Our top choices for Litchfield County holiday rentals

Dining

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is €370
includes taxes & fees
30 Jun - 1 Jul
Art House 3 Beds Close to Warner Theater
Terrace/patio

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is €225
includes taxes & fees
3 Jul - 4 Jul
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Interior

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is €133
includes taxes & fees
3 Jul - 4 Jul
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is €345
includes taxes & fees
6 Jul - 7 Jul
Litchfield Retreat, Wineries, Foliage & Skiing
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 €357
includes taxes & fees
29 Jun - 30 Jun
Cozy Modern Farmhouse Private Apt - 3 Beds
Smart TV, fireplace, books

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (16 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is €164
includes taxes & fees
1 Jul - 2 Jul
Mid Century Modern Studio w/ Full Kitchen - Newly Built
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 €480
includes taxes & fees
29 Jun - 30 Jun
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Exterior

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is €181
includes taxes & fees
6 Jul - 7 Jul
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Fridge, microwave, oven, stovetop

The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"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."
United States
Jennifer A.
The price is €333
includes taxes & fees
8 Jul - 9 Jul
The Jefferson Guest House, Spacious, Special Views
Dining

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is €785
includes taxes & fees
6 Jul - 7 Jul
Whispering Estate Guest House - A Romantic Countryside Getaway
Exterior

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
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 €269
includes taxes & fees
27 Jul - 28 Jul
Cozy Attic 10 min to Llitchfield
Interior

Coming Soon! #32- Sleeps 10!

Coming Soon! #32- Sleeps 10!
Plymouth
8.0 out of 10, Very good, (1 review)
"Everything was great, just 2 things… Is only 1 tv for the whole apartment, and there is another apartment upstairs and you can hear everything….other than that everything was great."
United States
Humberto H.
Coming Soon! #32- Sleeps 10!
1 bedroom, desk, iron/ironing board, WiFi

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is €362
includes taxes & fees
6 Jul - 7 Jul
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Outdoor dining

Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (54 reviews)
"Amazing weekend stay! The place was clean, cozy, and thoughtfully prepared. The host was responsive and welcoming. Would definitely book again!"
United States
Kelsey
The price is €1,809
includes taxes & fees
30 Jun - 1 Jul
Candlewood Lake Retreat with Private Dock
Dining

Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (76 reviews)
"Spacious"
United States
Mehul
The price is €206
includes taxes & fees
29 Jun - 30 Jun
Spacious 2 Bedroom apartment close to Yale Bowl
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, (147 reviews)
"Great location"
United States
Will G.
The price is €313
includes taxes & fees
9 Jul - 10 Jul
Big farmhouse in the foothills of the Berkshires
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
The price is €183
includes taxes & fees
28 Jul - 29 Jul
Hoppy Hill Farm House
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (33 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
Cozy One Bedroom Apartment Centrally Located in Southbury
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is €261
includes taxes & fees
29 Jun - 30 Jun
All New 1BR with tons of Charm
Exterior

Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.0 out of 10, Wonderful, (14 reviews)
"Conveniently located and nice, practically appointed stay for a business trip to work with a collaborator in town."
United States
Jeremy Y.
The price is €217
includes taxes & fees
29 Jun - 30 Jun
Bright Downtown Studio near Yale & East Rock!
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 Litchfield County Hotel Reviews

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

8/10 Good
"Wish there was an alarm clock on our room. Only negative. Hostess was amazing, friendly and accommodating when we asked to keep things in the refrigerator."
Marcia 1-night trip
Posted 20 hours ago
Locust Tree Bed and Breakfast LLC

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Holiday Homes in Litchfield County

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