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

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Litchfield vacation 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, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is ￥18,179
￥33,315 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A two-story house with a porch, a front door with a wreath, and a small garden area.

2. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (11 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is ￥18,353
￥53,750 total
includes taxes & fees
Oct 18 - Oct 19
Bear Retreat - 2-bedroom house in Waterbury
A spacious living room with large windows, a fireplace, and a view of the outdoors.

3. 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 ￥34,620
￥85,364 total
includes taxes & fees
Oct 16 - Oct 17
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

4. 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 ￥17,389
￥23,159 total
includes taxes & fees
Oct 22 - Oct 23
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
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 ￥10,670
￥22,705 total
includes taxes & fees
Nov 3 - Nov 4
Cozy private room in a shared home with a Full-size bed and private bathroom.
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

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

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
10.0 out of 10, Exceptional, (1 review)
"We loved the place, which feels like your own house in the woods. The setting is gorgeous especially with the leaves changing colors. We specifically chose the location so we could bike the Farmington Trail loop which starts at the bottom of the hill. The house is so well stocked with everything you could think of, especially coffee and there is plenty of space to relax inside and out. The host was very attentive to our needs. It couldn’t have been better for us."
United States
Margaret A.
The price is ￥27,885
￥35,229 total
includes taxes & fees
Nov 2 - Nov 3
Collinsville River Escape / Fall Foliage, Deck & Yard
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 ￥44,262
￥122,678 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥10,767
￥41,251 total
includes taxes & fees
Oct 26 - Oct 27
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, (74 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is ￥49,321
￥83,569 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥426,816
￥554,068 total
includes taxes & fees
Oct 17 - Oct 18
Las Flores Villa
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

11. #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 ￥32,919
￥73,801 total
includes taxes & fees
Oct 20 - Oct 21
#27- Luxury Collection
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.

12. 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 ￥16,646
￥50,523 total
includes taxes & fees
Oct 18 - Oct 19
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
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 traveler
The price is ￥27,664
￥71,035 total
includes taxes & fees
Oct 20 - Oct 21
The Old Avon 1800 Manor
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

14. 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 ￥39,409
￥114,853 total
includes taxes & fees
Oct 29 - Oct 30
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.

15. 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 ￥82,992
￥137,727 total
includes taxes & fees
Oct 27 - Oct 28
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.

16. 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 ￥28,028
￥67,507 total
includes taxes & fees
Nov 9 - Nov 10
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.

17. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is ￥71,136
￥108,370 total
includes taxes & fees
Oct 25 - Oct 26
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

Rocky River Inn

Rocky River Inn

8/10 Good
"Nothing fancy, but basic needs met. AC/heat, microwave, fridge, coffee maker, iron and ironing board, tv. Beds were comfy. Pillows could be better. We had a large double room. Lots of space! Two tables with chairs. Bathroom had soap, shampoo, conditioner. Easy place to stay, with close access to New Milford."
Sarah 3-night trip
Posted 8 hours ago
Rocky River Inn

Find out more about Litchfield

Litchfield Vacation Homes information

Number of reviews
192
Accommodation
236 Vacation Homes
Lowest Price
￥22,705
Highest Price
￥554,068