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

Litchfield County Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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
9.6 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 AU$519
includes taxes & fees
27 Oct - 28 Oct
Cozy Attic 10 min to Llitchfield
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

2. 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 AU$200
includes taxes & fees
9 Nov - 10 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A wooden cabin interior with a bench, a rug, and a hanging plant.

3. 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 AU$282
includes taxes & fees
8 Nov - 9 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

4. 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 AU$205
includes taxes & fees
18 Nov - 19 Nov
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
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 AU$302
includes taxes & fees
29 Oct - 30 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

6. 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 AU$636
includes taxes & fees
28 Oct - 29 Oct
Sharon Retreat w/ Private Yard
A two-story house with a front porch, a small balcony, and a white picket fence.

7. 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.
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.

8. 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 AU$395
includes taxes & fees
27 Oct - 28 Oct
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 AU$633
includes taxes & fees
29 Oct - 30 Oct
Art House 3 Beds Close to Warner Theater
A bedroom with a bed, a nightstand, a hanging light, and a window.

10. 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 AU$391
includes taxes & fees
27 Oct - 28 Oct
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

11. 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.
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

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 AU$547
includes taxes & fees
27 Oct - 28 Oct
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 AU$746
includes taxes & fees
16 Nov - 17 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 AU$834
includes taxes & fees
27 Oct - 28 Oct
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A rustic cabin surrounded by a forest with a stream in the foreground.

15. 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 AU$972
includes taxes & fees
25 Nov - 26 Nov
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
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!
3.0 star property
Oakville
The price is AU$766
includes taxes & fees
27 Oct - 28 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A hot tub in a covered outdoor area with a view of trees and a fence.

17. 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 AU$1,083
includes taxes & fees
27 Oct - 28 Oct
Lakehaven • Hot Tub, Decks, Fires & More
A hot tub in a backyard with a house, trees, and a clear sky.

18. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is AU$4,982
includes taxes & fees
27 Oct - 28 Oct
Las Flores Villa
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.

19. 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 AU$1,219
includes taxes & fees
27 Oct - 28 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Litchfield County Hotel Reviews

Rocky River Inn

Rocky River Inn

10/10 Excellent
"Very clean and updated. Very conveniently located"
Keith 2-night trip
Posted less than an hour ago
Rocky River Inn

Find out more about Litchfield County

Everything you need to know about Litchfield County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Litchfield County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Litchfield County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Litchfield County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Litchfield County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Litchfield County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Litchfield County holiday rentals we have chosen for you start as low as AU$200 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Litchfield County rentals

At Expedia, we put the best Litchfield County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Litchfield County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Litchfield County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Litchfield County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.