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Litchfield County Vacation Rentals

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Top Cities in Litchfield County

A mountainous landscape with autumn foliage, a valley, and distant buildings.
Vacation RentalsVacation Rentals

Watertown

Watertown

Our top choices for Litchfield County vacation 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)
"Clean property, very cute. Also very small. Cable/tv access was challenging, but all on all a good experience"
United States
traci
The price is CA $180
CA $339 total
includes taxes & fees
Oct 12 - Oct 13
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
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 CA $307
CA $397 total
includes taxes & fees
Oct 12 - Oct 13
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
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 CA $236
CA $305 total
includes taxes & fees
Oct 13 - Oct 14
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 CA $214
CA $628 total
includes taxes & fees
Oct 28 - Oct 29
Cozy Modern Farmhouse Private Apt - 3 Beds
A two-story house with a front porch, a small balcony, and a white picket fence.

5. 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 CA $154
CA $536 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Attic 10 min to Llitchfield
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

6. 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 CA $257
CA $432 total
includes taxes & fees
Nov 9 - Nov 10
Pristine Cozy Walkable Downtown 2BR Getaway
A wooden cabin interior with a bench, a rug, and a hanging plant.

7. 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 CA $164
CA $300 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

8. 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 CA $204
CA $621 total
includes taxes & fees
Nov 1 - Nov 2
Art House 3 Beds Close to Warner Theater
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

9. 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 CA $487
CA $856 total
includes taxes & fees
Nov 10 - Nov 11
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.

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 CA $439
CA $567 total
includes taxes & fees
Oct 29 - Oct 30
The Jefferson Guest House, Spacious, Special Views
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

11. 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 CA $421
CA $812 total
includes taxes & fees
Nov 2 - Nov 3
Escape to Bantam Lake- With Fireplace and Hot tub!
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

12. 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 CA $135
CA $184 total
includes taxes & fees
Nov 9 - Nov 10
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
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!
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 CA $312
CA $774 total
includes taxes & fees
Oct 12 - Oct 13
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!
3.0 star property
Oakville
The price is CA $389
CA $769 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $83
CA $190 total
includes taxes & fees
Oct 13 - Oct 14
Cozy private room in a shared home with a Full-size bed and private bathroom.
A rustic cabin surrounded by a forest with a stream in the foreground.

16. 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 CA $455
CA $820 total
includes taxes & fees
Oct 13 - Oct 14
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.

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 CA $494
CA $1,237 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $3,849
CA $4,997 total
includes taxes & fees
Oct 12 - Oct 13
Las Flores Villa
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

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
The price is CA $674
CA $1,155 total
includes taxes & fees
Oct 14 - Oct 15
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A wooden wall with a large mirror, a wooden console table, and two wall-mounted lanterns.

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is CA $199
CA $602 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
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
"Wonderful stay! Beautiful property and pool, breakfast was delicious."
Jacqueline 1-night trip
Posted 1 day ago
The Litchfield Inn

Find out more about Litchfield County

Everything you need to know about Litchfield County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Litchfield County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Litchfield County vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Litchfield County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Litchfield County vacation rentals we have selected for you start as low as CA $190 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 vacation 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 vacation.

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.