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 hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

1. 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, (55 reviews)
"It was a nice stay…worked well for the event we attended in town. The host was very nice to work with"
United States
Roberta S.
The price is €186
includes taxes & fees
22 Nov - 23 Nov
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A two-story house with a front porch, a small balcony, and a white picket fence.

2. 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 €320
includes taxes & fees
19 Nov - 20 Nov
Cozy Attic 10 min to Llitchfield
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
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is €185
includes taxes & fees
13 Nov - 14 Nov
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A wooden cabin interior with a bench, a rug, and a hanging plant.

4. 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, (5 reviews)
The price is €172
includes taxes & fees
17 Nov - 18 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

5. 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 €119
includes taxes & fees
20 Nov - 21 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A wooden wall with a large mirror, a wooden console table, and two wall-mounted lanterns.

6. Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is €364
includes taxes & fees
15 Nov - 16 Nov
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

7. 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, (21 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is €239
includes taxes & fees
12 Nov - 13 Nov
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.

8. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (22 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is €253
includes taxes & fees
16 Nov - 17 Nov
Pristine Cozy Walkable Downtown 2BR Getaway
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

9. 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 €386
includes taxes & fees
12 Nov - 13 Nov
Art House 3 Beds Close to Warner Theater
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

10. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
The price is €406
includes taxes & fees
13 Nov - 14 Nov
Sharon Retreat w/ Private Yard
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

11. Spa Cabin with Sauna, Hot Tub and Cold Plunge

Spa Cabin with Sauna, Hot Tub and Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (7 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is €483
includes taxes & fees
30 Nov - 1 Dec
Spa Cabin with Sauna, Hot Tub and Cold Plunge
A spacious kitchen with wooden cabinets, a large island with stools, and a clock on the wall.

12. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 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 €340
includes taxes & fees
15 Nov - 16 Nov
The Jefferson Guest House, Spacious, Special Views
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

13. 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, (6 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 €513
includes taxes & fees
22 Nov - 23 Nov
Escape to Bantam Lake- With Fireplace and Hot tub!
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

14. 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 €504
includes taxes & fees
12 Nov - 13 Nov
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A spacious living room with large windows, a fireplace, and a view of the outdoors.

15. 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 €480
includes taxes & fees
12 Nov - 13 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A rustic cabin surrounded by a forest with a stream in the foreground.

16. Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Creek Side Cabin w/ Wood Fired Hot Tub & 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 €475
includes taxes & fees
12 Nov - 13 Nov
Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit
A hot tub in a backyard with a house, trees, and a clear sky.

17. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is €1,274
includes taxes & fees
12 Nov - 13 Nov
Las Flores Villa
A spacious living room with large windows, a fireplace, and a view of the outdoors.

18. 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 €458
includes taxes & fees
12 Nov - 13 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A two-story house with a front porch, a small balcony, and a white picket fence.

19. 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 €367
includes taxes & fees
12 Nov - 13 Nov
Cozy Modern Farmhouse Private Apt - 3 Beds
A living room with a white sectional sofa, a dining area with a wooden table and chairs, and a staircase leading to an upper level.

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, (2 reviews)
"The house was perfect for our girls weekend. It was even nicer in person."
United States
Lauren B.
The price is €710
includes taxes & fees
12 Nov - 13 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

Homestead Inn

Homestead Inn

10/10 Excellent
"This was such a great place to stay and a really great location in New Milford Connecticut. We were right down the block from all of the main shops and restaurants, and we were in love with the rustic and cozy ambience of the homestead inn. Tara and Antonio were so warm and friendly to us. If we go back, we would definitely stay here again"
Kerry 2-night trip
Posted 7 hours ago
Homestead Inn

Find out more about Litchfield County

Holiday Homes in Litchfield County

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