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Holiday Homes in Litchfield

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Litchfield and around

Spacious Home nestled along the Blackberry River in Northwest CT
Fridge, microwave, oven, stovetop

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"The team stayed here for a curling tournament. Great location for that and perfect for 4 non-couple guests"
Spacious Home nestled along the Blackberry River in Northwest CT
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Outdoor dining

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

9.0 out of 10, Wonderful, (19)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Lake Oasis with Firepit, Game room and Kayaks
Smart TV, ping pong

Lake Oasis with Firepit, Game room and Kayaks

10.0 out of 10, Exceptional, (1)
"This was our family's first time to Candlewood Lake/Squantz Pond. The area is picturesque and the location of this property is perfect. The porch off of the living area directly overlooks Squantz Pond and mountains. The basement was ideal for teenagers with a projector screen, air hockey/pool, and exercise equipment. The bedroom were spacious and beds comfortable. The kitchen/living area are open concept and the whole family could be together. The owner and his daughter are incredibly kind and...
Lake Oasis with Firepit, Game room and Kayaks
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (58)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is €397
includes taxes & fees
19 Aug - 20 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Tranquil Litchfield Connecticut Retreat".
Property grounds

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (15)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is €284
includes taxes & fees
18 Aug - 19 Aug
Tranquil Litchfield Connecticut Retreat".
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Terrace/patio

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Private Annex/Former Artist Studio
Exterior detail

Private Annex/Former Artist Studio

10.0 out of 10, Exceptional, (51)
"Great property great location wonderful day"
Private Annex/Former Artist Studio
Relax or be active! The choice is yours in this pet-friendly family home.
Fridge, microwave, oven, stovetop

Relax or be active! The choice is yours in this pet-friendly family home.

9.8 out of 10, Exceptional, (14)
"Home was exactly as listed, very comfortable and convenient for my family’s trip. "
Relax or be active! The choice is yours in this pet-friendly family home.
Charming 1870 cape cottage in Litchfield
Outdoor pool

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (52)
"Great location and beautiful setting. Was perfect for the two of us."
Charming 1870 cape cottage in Litchfield
Woodland A-Frame
Interior

Woodland A-Frame

10.0 out of 10, Exceptional, (1)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame
Mountaintop Horse Farm with Heated Pool
Outdoor pool, a heated pool

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (31)
"This a the most unique place! A very clean and comfortable apartment above a barn with beautiful horses and more. Wonderful hosts too. We hope to be back! "
Mountaintop Horse Farm with Heated Pool
Cozy Lakefront Bungalow w firepit/dock/kayaks
Terrace/patio

Cozy Lakefront Bungalow w firepit/dock/kayaks

9.8 out of 10, Exceptional, (30)
"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
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (6)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Interior

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (27)
"Clean, Cozy and Comfortable "
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
Property grounds

Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

2.0 star property
10.0 out of 10, Exceptional, (9)
"We met our kids (who live on the east coast) at Natures Nest and really enjoyed our time here. We cooked 2 big meals and the kitchen had everything we needed…even spices & coffee. And Marco left some apples, sweets and wine for us! He was very responsive and helpful anytime we had questions, and gave us great recommendations. Everything was great!"
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
County Seat Colonial
2 bedrooms, iron/ironing board, WiFi, bed sheets

County Seat Colonial

10.0 out of 10, Exceptional, (11)
"This was just what we needed. Thank you for a beautiful home, adorable town and so much to do! Perfect weekend for my family!"
County Seat Colonial
#26 Beautifully Renovated 2 BR Home
Fridge, microwave, oven, stovetop

#26 Beautifully Renovated 2 BR Home

10.0 out of 10, Exceptional, (2)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
#26 Beautifully Renovated 2 BR Home
Charming Home with Fireplace and Indoor Pool in Sharon, CT
Terrace/patio

Charming Home with Fireplace and Indoor Pool in Sharon, CT

10.0 out of 10, Exceptional, (1)
"Our family had a wonderful stay at the beautiful, clean, peaceful Hoyt House. There was plenty of space to gather together as well as spread out. The daffodils were beginning to bloom and there is the sight and sound of a running stream behind the home. We were close to fun things to explore like the Audubon, covered bridge, and Kent waterfalls. Great bakery, restaurants, grocery a short drive away. The heated indoor swimming pool was the biggest hit. We hope to have the opportunity to...
Charming Home with Fireplace and Indoor Pool in Sharon, CT
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Dining

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Fridge, microwave, oven, stovetop

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
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

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

10/10 Excellent
"Nice"
Fabiola 2-night trip
Posted 16 hours ago
Courtyard by Marriott Waterbury Downtown