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

Litchfield County Holiday Rentals

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Our top choices for Litchfield County holiday rentals

A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

1. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is HK$2,847
HK$4,787 total
includes taxes & fees
10 Nov - 11 Nov
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

2. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (19 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is HK$1,687
HK$2,160 total
includes taxes & fees
18 Oct - 19 Oct
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

3. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (22 reviews)
"It was great!"
United States
Amanda T.
The price is HK$1,530
HK$2,507 total
includes taxes & fees
9 Nov - 10 Nov
Pristine Cozy Walkable Downtown 2BR Getaway
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

4. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (5 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is HK$2,001
HK$4,063 total
includes taxes & fees
2 Nov - 3 Nov
Escape to Bantam Lake- With Fireplace and Hot tub!
A living room with a fireplace, two armchairs, a sofa, and a TV.

5. 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, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is HK$1,530
HK$1,956 total
includes taxes & fees
2 Nov - 3 Nov
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A two-story house with a front porch, a small balcony, and a white picket fence.

6. 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 HK$1,096
HK$3,311 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Modern Farmhouse Private Apt - 3 Beds
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

7. 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 HK$1,123
HK$3,409 total
includes taxes & fees
2 Nov - 3 Nov
Art House 3 Beds Close to Warner Theater
A two-story house with a front porch, a small balcony, and a white picket fence.

8. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is HK$725
HK$2,782 total
includes taxes & fees
3 Nov - 4 Nov
Cozy Attic 10 min to Llitchfield
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

9. 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 HK$1,871
HK$4,625 total
includes taxes & fees
20 Oct - 21 Oct
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

10. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
The price is HK$2,288
HK$2,955 total
includes taxes & fees
19 Oct - 20 Oct
The Jefferson Guest House, Spacious, Special Views
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

11. 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
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$808
HK$1,086 total
includes taxes & fees
16 Nov - 17 Nov
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A wooden cabin interior with a bench, a rug, and a hanging plant.

12. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is HK$902
HK$1,654 total
includes taxes & fees
1 Nov - 2 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A spacious living room with large windows, a fireplace, and a view of the outdoors.

13. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is HK$2,142
HK$4,230 total
includes taxes & fees
17 Oct - 18 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A spacious living room with large windows, a fireplace, and a view of the outdoors.

14. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
9.0 out of 10, Wonderful, (6 reviews)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
United States
Elizabeth H.
The price is HK$1,718
HK$4,214 total
includes taxes & fees
17 Oct - 18 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

15. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is HK$530
HK$1,127 total
includes taxes & fees
3 Nov - 4 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A hot tub in a backyard with a house, trees, and a clear sky.

16. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is HK$21,187
HK$27,503 total
includes taxes & fees
17 Oct - 18 Oct
Las Flores Villa
A rustic cabin surrounded by a forest with a stream in the foreground.

17. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is HK$2,681
HK$4,681 total
includes taxes & fees
20 Oct - 21 Oct
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A living room with a sectional sofa, a small side table, and a floor lamp.

18. Lakehaven • Hot Tub, Decks, Fires & More

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
10.0 out of 10, Exceptional, (1 review)
"Great find!! Amazing views, house was superb!"
United States
Iva B.
The price is HK$2,197
HK$6,090 total
includes taxes & fees
18 Oct - 19 Oct
Lakehaven • Hot Tub, Decks, Fires & More
A modern interior with a central light fixture, seating arrangement, and large windows.

19. 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.
The price is HK$1,528
HK$3,727 total
includes taxes & fees
19 Oct - 20 Oct
Coming Soon! #32- Sleeps 10!
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

20. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
The price is HK$4,120
HK$6,829 total
includes taxes & fees
2 Nov - 3 Nov
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
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

Rocky River Inn

Rocky River Inn

10/10 Excellent
"Marvelous! The room was fantastic and the staff was professional and extremely courteous. The river behind the property was breathtaking and definitely a photo op. Overall, a top-tier place to stay. Highly recommend!"
Stephen 1-night trip
Posted 1 hour ago
Rocky River Inn