Photo by Jennifer Magri

Holiday Homes in Litchfield

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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Featured Holiday Homes in Litchfield

Escape to a Celebrity Chef's Waterfront Lake House
Interior

Escape to a Celebrity Chef's Waterfront Lake House

10.0 out of 10, Exceptional, (1)
Escape to a Celebrity Chef's Waterfront Lake House
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
On the beach, sun-loungers

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

9.6 out of 10, Exceptional, (83)
"No complaints. Stayed during the winter so ne er got the full experience with the lake but it was a great home."
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Smart TV, fireplace, ping pong, stereo

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.8 out of 10, Exceptional, (22)
"We made happy memories over a cold January weekend. We cooked together, sat around the fire, played games and dozed in comfortable beds with high quality linens. We enjoyed the view of the water and the twinkling lights on the property at night. The steam shower was divine. If you like cooking, bring good knives, a veggie peeler and good pans. Plenty of glassware and dishes and some cookware provided. "
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
The Goshen Glass Chalet
Outdoor dining

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (31)
"Our weekend stay here was absolutely amazing. The house was spotless and had all the conveniences of home. The owner was quick to respond to any questions that we had. The hot tub was absolutely a selling point for us. We were so relaxed in this spacious house from the fully stocked kitchen, to the bathrobes, to the Awesome outside, screened in porch. The kids had a blast in the basement with ping pong, and the games stocked in the closet. I would love to come back in the spring and summer to...
The Goshen Glass Chalet
Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT
Exterior

Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT

2.0 star property
Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT
NEW-Another Fun Downtown Location 1st floor
Interior

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (9)
"It was a nice quiet valuable time spent together .just what we needed for that very special memorable time. Thanks."
NEW-Another Fun Downtown Location 1st floor
Renovated, one level home in an excellent location
Fridge, microwave, oven, stovetop

Renovated, one level home in an excellent location

10.0 out of 10, Exceptional, (39)
"We had a great stay! "
Renovated, one level home in an excellent location
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Outdoor dining

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (18)
"We had a friend group boardgaming weekend and this was perfect for our purposes. The table was large enough for our biggest games and the pool table doubled as a backup playing space. The race cars are a nice touch of whimsy too :-) Our only suggestion would be to replace the oversized, too-low chandelier over the table but really only a minor thing."
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (85)
"Place is great. Has a old farmhouse feel with an update. Lots of spots within the house for people to hang out. We did a family birthday get together and had a great time. "
Antique Farmhouse Totally Restored
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Fridge, microwave, stovetop, dishwasher

Serene Salisbury Rental Home on 26 Acres w/ Deck!

9.8 out of 10, Exceptional, (8)
"We had a wonderful time in your beautiful home. Went on many hikes and drives to Great Barrington, Lenox, Salisbury and a few other towns. We saw the Christmas lights in Lenox, ate at GB Eats and the Black Rabbit. We played games, assembled puzzles and relaxed. The fireplace kept us warm and cozy. It was a wonderful place to bond with our family and spend the holiday weekend together. Many thanks for everything!"
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated
Fridge, microwave, oven, stovetop

Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

9.8 out of 10, Exceptional, (9)
"We loved our stay! Andrea responded to questions very quickly. The house was very clean and had everything we needed. We appreciated the treat that was left on the island. We were there only 2 nights and wish we stayed longer. We would definitely stay again. "
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated
Cozy Lakefront Bungalow w firepit/dock/kayaks
Terrace/patio

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (25)
"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
The Connecticut Chalet - On 5 Acres!
Interior

The Connecticut Chalet - On 5 Acres!

10.0 out of 10, Exceptional, (2)
"If you’re looking for a relaxing, unique/fun home this is it!! The host was amazing & left no questions to ask. The home is fully stocked with all your needs from cooking utensils, wood to start a warm fire & even games for in between time. The bedrooms are cozy and the beds are super soft. The deck & sun room/dining room was a fav, the views are amazing. I would certainly recommend and even stay here again. Thank you "
The Connecticut Chalet - On 5 Acres!
The Art House: 5-Acre Private Getaway w/ Firepit & AC
Interior

The Art House: 5-Acre Private Getaway w/ Firepit & AC

9.8 out of 10, Exceptional, (13)
"Great weekend "
The Art House: 5-Acre Private Getaway w/ Firepit & AC
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
Terrace/patio

Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer

10.0 out of 10, Exceptional, (1)
"Beautiful home, worked well for 10 adults. Great hosts, well stocked with everything we needed. Clean, comfy, cozy! Would recommend to friends and family! "
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
Bluebird Valley Farmhouse
Beach

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (60)
"This house is perfection! The layout is wonderful, and the decor was lovely. The kitchen is fully equipped. The beds are ridiculously comfortable. The wifi was super fast. Do not hesitate to book this house?"
Bluebird Valley Farmhouse
Cozy Litchfield House w/ Fenced-In Yard & Fire Pit
Terrace/patio

Cozy Litchfield House w/ Fenced-In Yard & Fire Pit

9.8 out of 10, Exceptional, (62)
"House was clean, completely stocked with everything needed and more, great back yard and gathering areas. Property owner helped right away when we reached out. Would definitely recommend. "
Cozy Litchfield House w/ Fenced-In Yard & Fire Pit
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
Fridge, microwave, oven, stovetop

Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

10.0 out of 10, Exceptional, (39)
"Excellent stay in s as wonderful house. "
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Interior

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (19)
"Very nice clean house. Felt like coming home after work"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Stylish & Luxurious 3 BDR Home with Play Station
Fridge, microwave, oven, stovetop

Stylish & Luxurious 3 BDR Home with Play Station

9.4 out of 10, Exceptional, (9)
"We needed a place for our family of 6 to stay while visiting family in the area. This place was exactly what we needed, as advertised, and the owner was quick with communications. We would definitely stay here again!"
Stylish & Luxurious 3 BDR Home with Play Station
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
Fridge, microwave, oven, stovetop

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (55)
"Great place to end our Gilmore Girls adventure!!! The Hideaway was clean and cozy, and the hosts are very professional! We would stay here again!!!!"
The price is AU$405
includes taxes & fees
19 Mar - 20 Mar
Litchfield Hills Hideaway
The Jefferson House, Charming, Exceptional, Spacious Home, Estate in Litchfield
1 bedroom, desk, iron/ironing board, WiFi

The Jefferson House, Charming, Exceptional, Spacious Home, Estate in Litchfield

10.0 out of 10, Exceptional, (1)
"The lighting is warm and inviting as you step up the stairs into a large open concept room. Every detail is beyond modern from the giant marble counter equipped with the comfiest and largest leather barstools, to the kitchen whose colors and appliances are so beautifully designed; cabinets stocked with every item you need to cook a homemade meal.The king size bed was like a cloud, swallowing us in the fluffiest duvets and sheets, comfortable pillows, making it an easy switch to use the TV in the...
The price is AU$594
includes taxes & fees
23 Feb - 24 Feb
The Jefferson House, Charming, Exceptional, Spacious Home, Estate in Litchfield
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
On the beach, sun-loungers

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

9.6 out of 10, Exceptional, (83)
"No complaints. Stayed during the winter so ne er got the full experience with the lake but it was a great home."
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
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.