A covered bridge with a sign reading 'West Cornwall' and a '10'-11' height clearance warning.

Holiday Homes in Litchfield

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Litchfield holiday homes

A wooden cabin interior with a bench, a rug, and a hanging plant.

1. 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 NZ$375
includes taxes & fees
1 Nov - 2 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

2. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is NZ$260
includes taxes & fees
12 Oct - 13 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A two-story house with a porch, a front door with a wreath, and a small garden area.

3. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is NZ$608
includes taxes & fees
12 Oct - 13 Oct
Bear Retreat - 2-bedroom house in Waterbury
A spacious living room with large windows, a fireplace, and a view of the outdoors.

4. 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 NZ$958
includes taxes & fees
12 Oct - 13 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

5. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
The price is NZ$356
includes taxes & fees
13 Oct - 14 Oct
Collinsville River Escape / Fall Foliage, Deck & Yard
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

6. 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, (2 reviews)
"Clean and close to activitys"
United States
randall
The price is NZ$277
includes taxes & fees
13 Oct - 14 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A living room with a sectional sofa, a small side table, and a floor lamp.

7. 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 NZ$1,521
includes taxes & fees
13 Oct - 14 Oct
Lakehaven • Hot Tub, Decks, Fires & More
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

8. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (4 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is NZ$463
includes taxes & fees
26 Oct - 27 Oct
Sun Filled Lake House Living
A patio with a table and chairs, a grill, and a view of a lake.

9. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (73 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is NZ$928
includes taxes & fees
19 Oct - 20 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A hot tub in a backyard with a house, trees, and a clear sky.

10. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is NZ$6,232
includes taxes & fees
9 Oct - 10 Oct
Las Flores Villa
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

11. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is NZ$687
includes taxes & fees
9 Oct - 10 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

12. #27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is NZ$825
includes taxes & fees
20 Oct - 21 Oct
#27- Luxury Collection
A patio area with wicker furniture and a brick floor.

13. The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
7.0 out of 10, Good, (2 reviews)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveller
The price is NZ$795
includes taxes & fees
12 Oct - 13 Oct
The Old Avon 1800 Manor
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

14. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is NZ$595
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

15. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is NZ$1,263
includes taxes & fees
28 Oct - 29 Oct
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

16. 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 NZ$1,424
includes taxes & fees
15 Oct - 16 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

17. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$769
includes taxes & fees
12 Oct - 13 Oct
Cheerful 3-bedroom cottage with woodstove
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

18. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is NZ$1,209
includes taxes & fees
12 Oct - 13 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
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 Hotel Reviews

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

10/10 Excellent
"Hotel staff was so accommodating and the whole place was very clean and well kept. Will def return again."
Polina 2-night trip
Posted 5 hours ago
Holiday Inn Cheshire - Southington by IHG

Find out more about Litchfield

Litchfield Holiday Homes information

Number of reviews
188
Accommodation
238 Holiday Homes
Lowest Price
NZ$260
Highest Price
NZ$6,232