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

A two-story house with a front porch, a small balcony, and a white picket fence.

1. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 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 €308
includes taxes & fees
28 Sept - 29 Sept
Cozy Attic 10 min to Llitchfield
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

2. 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
9.4 out of 10, Exceptional, (52 reviews)
"Quaint very nice loved the space very cozy the hot tub was a nice touch I did use that a few times helped my sore back LOL everything went as expected I would stay here again"
United States
paul
The price is €216
includes taxes & fees
28 Sept - 29 Sept
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A living room with a fireplace, two armchairs, a sofa, and a TV.

3. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
The price is €189
includes taxes & fees
1 Oct - 2 Oct
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.

4. 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 €358
includes taxes & fees
28 Sept - 29 Sept
Cozy Modern Farmhouse Private Apt - 3 Beds
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

5. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (21 reviews)
"It was great!"
United States
Amanda T.
The price is €250
includes taxes & fees
28 Sept - 29 Sept
Pristine Cozy Walkable Downtown 2BR Getaway
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

6. 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 €118
includes taxes & fees
26 Oct - 27 Oct
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
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 €375
includes taxes & fees
30 Sept - 1 Oct
Art House 3 Beds Close to Warner Theater
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

8. 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, (1 review)
"Clean and close to activitys"
United States
randall
The price is €144
includes taxes & fees
13 Oct - 14 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

9. 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, (17 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is €249
includes taxes & fees
28 Sept - 29 Sept
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A wooden cabin interior with a bench, a rug, and a hanging plant.

10. 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, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is €199
includes taxes & fees
4 Oct - 5 Oct
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

11. 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 €356
includes taxes & fees
28 Sept - 29 Sept
The Jefferson Guest House, Spacious, Special Views
A modern interior with a central light fixture, seating arrangement, and large windows.

12. 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!
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

13. 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 €513
includes taxes & fees
30 Sept - 1 Oct
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
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!
3.0 star property
Oakville
The price is €473
includes taxes & fees
28 Sept - 29 Sept
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

15. 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, (4 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 €716
includes taxes & fees
10 Oct - 11 Oct
Escape to Bantam Lake- With Fireplace and Hot tub!
A spacious living room with large windows, a fireplace, and a view of the outdoors.

16. 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 €468
includes taxes & fees
28 Sept - 29 Sept
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
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.
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

18. 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 €601
includes taxes & fees
18 Oct - 19 Oct
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A hot tub in a backyard with a house, trees, and a clear sky.

19. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is €3,077
includes taxes & fees
1 Oct - 2 Oct
Las Flores Villa
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
The price is €686
includes taxes & fees
28 Sept - 29 Sept
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

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"The personell at the Inn were excellent, couldn't do enough for you. The room was clean and well maintained. The breakfast was great!!"
Kenneth 1-night trip
Posted 7 hours ago
The Litchfield Inn

Find out more about Litchfield County

Holiday Homes in Litchfield County

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