Photo by Jennifer Magri

Holiday Homes in Litchfield

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Featured Holiday Homes in Litchfield

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is AU$748
includes taxes & fees
6 Oct - 7 Oct
Cheerful 3-bedroom cottage with woodstove
Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (31)
"Beautiful house"
Charming 1870 cape cottage in Litchfield
NEW-Another Fun Downtown Location 1st floor
2.0 star property
10.0 out of 10, Exceptional, (2)
"I was fairly new to VRBO, host helped alot with some things I missed (thanks!), and I am sure that was a hassle for him. He was very responsive, I met him and he is very invested in doing well. The house is nice, roomy, wifi had no issues, window AC in every room, surprisingly quiet (AC was on), ample parking. Bathroom is small. Great coffee shops etc. short walk across the street."
NEW-Another Fun Downtown Location 1st floor
Cozy Lakefront Bungalow w firepit/dock/kayaks
10.0 out of 10, Exceptional, (23)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
Mountain View Getaway
10.0 out of 10, Exceptional, (41)
"This is our second year staying with at Karen and Larry’s property and it did not disappoint. They are incredible hosts and their home is conveniently located near the Lime Rock Track (less than 3 miles). It’s a beautiful and peaceful setting and extremely comfortable home. We highly recommend."
Mountain View Getaway
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (82)
"We had 15 people stay for three nights for a family reunion - 9 adults and 6 kids. The house worked well, as all had reasonably private spaces. The countryside is beautiful. Visits to a lake for swimming and several local waterfalls worked well for all."
Antique Farmhouse Totally Restored
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
9.4 out of 10, Exceptional, (8)
"Great property, very clean and host was quick to reply. We were impressed with the amenities available (most places don’t have detergent, etc) and the view was amazing! We didn’t have time to go to the dock but it looked very nice! Wish we had time to stay longer. We will definitely try to stay there again for our next family event"
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (23)
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. "
Family House On Highland Lake with Dock
Charming 3BR Hilltop House, Newly Remodeled with Arcade
10.0 out of 10, Exceptional, (16)
"Clean, Cozy and Comfortable "
Charming 3BR Hilltop House, Newly Remodeled with Arcade
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 13!*
10.0 out of 10, Exceptional, (2)
"The upstairs kitchen may need some extra ceramic bowls and silverware. The hot water may need to be turned up, it was tepid at best. Jeff was more than helpful getting us situated and comfortable. Great neighborhood, and availability to groceries, restaurants, and the great brewery 2 minutes away. Great room for families for togetherness and privacy"
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 13!*
Spacious & Modern Ashley Falls Home on 1 Acre
9.6 out of 10, Exceptional, (11)
"The house was well appointed, clean, quiet and convenient.We hope to return in the future."
Spacious & Modern Ashley Falls Home on 1 Acre
Enjoy your own private lake this summer! Boats, beach, lawn games & game room!
10.0 out of 10, Exceptional, (116)
"Three generations and two dogs thoroughly enjoyed the privacy, the quiet, the over the top amenities provided at this amazing house. We could not believe the thoughtfulness of both indoor and outdoor games, little extras everywhere, even for the dogs! We will absolutely be back."
Enjoy your own private lake this summer! Boats, beach, lawn games & game room!
Renovated, one level home in an excellent location
10.0 out of 10, Exceptional, (36)
"Perfect for my elderly parents with limited mobility. Close to Marina. Beautiful, quiet neighborhood."
Renovated, one level home in an excellent location
Litchfield County Getaway
10.0 out of 10, Exceptional, (37)
"We had a wonderful stay at Krystian’s place! The house is wonderful, welcoming and warm. It was very clean, fully equipped, included many special touches and the beds were very comfy. The host was easy to communicate with. We highly recommend this property and appreciate the time we had there. "
Litchfield County Getaway
Upscale Waterbury Retreat w/ Indoor Hot Tub!
9.8 out of 10, Exceptional, (8)
"Our stay was perfect. Comfortable beds, modern well equipped kitchen, beautiful appointments, clean everything. We had a family emergency, and the hosts were unbelievably nice and acommodating. The snow came and the hosts arranged for snow removal. Very caring and you can see a lot of effort to make guests comfortable and safe."
Upscale Waterbury Retreat w/ Indoor Hot Tub!
Enjoy a getaway on the scenic Housatonic River/Lake Lilinonah in New Milford, CT
9.2 out of 10, Wonderful, (5)
"We had a great time. It was a beautiful place and awesome views! Great for kayaking and floating in tubes."
Enjoy a getaway on the scenic Housatonic River/Lake Lilinonah in New Milford, CT
The Perfect Escape From The City
9.8 out of 10, Exceptional, (40)
"Busy running back and forth to Lime Rock for a car event, but able to enjoy a peaceful stay upon returning to the house. Highly recommend this house, but really don’t want to so I can have it all to myself, when needed."
The Perfect Escape From The City
Historic Cottage w Brand New Hot Tub and Game Room
10.0 out of 10, Exceptional, (1)
"Perfect mix of old and new. Wide plank floors, farmhouse sinks, low ceilings make it feel like you’ve gone back in time. Tastefully done updates offer modern conveniences. We had a wonderful stay."
Historic Cottage w Brand New Hot Tub and Game Room
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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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Other property types in Litchfield

Litchfield Hills Hideaway
10.0 out of 10, Exceptional, (51)
"The place was clean and very cozy. It had all the amenities it listed, the owners were very pleasant. I recommend this place to anyone looking for rest and relaxation."
The price is AU$383
includes taxes & fees
29 Sept - 30 Sept
Litchfield Hills Hideaway
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Fun Downtown Location 2nd flr
9.8 out of 10, Exceptional, (59)
"The apartment was very close to restaurants, breweries and a rails to trails path that went on for miles. Great location overall. "
Fun Downtown Location 2nd flr
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.