Photo by Jennifer Magri

Holiday Homes in Litchfield

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Litchfield

Private Annex/Former Artist Studio
Exterior detail
Private Annex/Former Artist Studio
10.0 out of 10, Exceptional, (46)
"The owner greeted us the first night. Very pleasant and super friendly. The space is beautiful and the fact that it was once an artist's studio for me made it even more special. The nearby lake is gorgeous. We brought our dog and she was very relaxed and comfortable for the stay. I thoroughly enjoyed the property and our mini vacation! "
Private Annex/Former Artist Studio
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Beach
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
10.0 out of 10, Exceptional, (90)
"Beautiful spot on the lake. Great house. "
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
On the beach, sun-loungers
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (73)
"Awesome stay!"
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Tranquil Litchfield Connecticut Retreat".
Property grounds
Tranquil Litchfield Connecticut Retreat".
9.8 out of 10, Exceptional, (6)
"They obviously care very much about the place. Everything was pristine. Beds were comfortable. Location was convenient. Everything was as advertised. "
The price is AU$481
includes taxes & fees
17 Nov - 18 Nov
Tranquil Litchfield Connecticut Retreat".
Lakefront Home, Close to Mt Southington!
Fridge, microwave, stovetop, dishwasher
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, (13)
"Staff very much enjoyed the atmosphere after long days of work. Wonderful Ownership. Thank you so much Susan!"
Lakefront Home, Close to Mt Southington!
Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop
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
The Goshen Glass Chalet
Outdoor dining
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (27)
"Wanted to visit my son in Litchfield around Halloween with my 2 teenaged granddaughters. The Goshen Glass Chalet was the perfect place for our visit. Loved every detail. "
The Goshen Glass Chalet
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Interior
Charming 3BR Hilltop House, Newly Remodeled with Arcade
10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Bluebird Valley Farmhouse
Beach
Bluebird Valley Farmhouse
10.0 out of 10, Exceptional, (59)
"If ever in the area again, we will definitely stay at Bluebird Farmhouse. It is so charming with wonderful artwork throughout this warm and comfortable home. A beautiful setting with a very well equipped home providing everything you need. We were in town for a wedding and thoroughly enjoyed our stay at this special farmhouse!!"
Bluebird Valley Farmhouse
Gather your family at this country estate
Miscellaneous
Gather your family at this country estate
10.0 out of 10, Exceptional, (3)
"This is an older home with charm. Lots of room, and while just six of us stayed, it appears more could be accommodated with inflatable mattresses. We enjoyed sitting outside by the simple fire pit one night. I would encourage the owners to put an outside light in the back as I stumbled on the stairs twice but that’s really the only issue. We are so sorry we misplaced one of the two keys,please send us a bill for a copy if you don’t find it. Thank you!"
Gather your family at this country estate
Mountain View Getaway
Outdoor dining
Mountain View Getaway
10.0 out of 10, Exceptional, (45)
"My daughter, granddaughter and I spent a wonderful weekend at this home. We enjoyed every second of the view, wildlife, peacefulness, and each other. We built puzzles, cooked wonderful meals, and relaxed. Beautiful home, perfectly kept, fun amenities, and wonderful hosts! We highly recommend."
Mountain View Getaway
Fickle Fox Farm. Leaf Peepers and Skiers! This is your season.
Miscellaneous
Fickle Fox Farm. Leaf Peepers and Skiers! This is your season.
10.0 out of 10, Exceptional, (11)
"What a property! Picturesque pictures, room for the whole family and then some. Wonderful kitchen and fireplace, fully stocked with wood and starter. The kids love the game room with fully stocked board games, card games, and outdoor toys for all kids and adults. Host was very responsive to any questions I had! Would definitely and will most likely stay again"
Fickle Fox Farm. Leaf Peepers and Skiers! This is your season.
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, (6)
"This was our second stay at this VRBO and hope to stay again on return trips to the area."
NEW-Another Fun Downtown Location 1st floor
Cheerful 3-bedroom cottage with woodstove
Property grounds
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (29)
"Sabrina saw to everything. The house even came equipped with a spice drawer, games like badminton equipment, a kid’s bedroom with games and books, and nice touches like vases of flowers. Our family was amazed and impressed. The outdoor area in the front (and back) was big enough for our grandchildren to play badminton. We very highly recommend this place!"
The price is AU$736
includes taxes & fees
18 Nov - 19 Nov
Cheerful 3-bedroom cottage with woodstove
Candlewood Lake Grand Waterfront Oasis: A Luxurious Family Retreat
Outdoor dining
Candlewood Lake Grand Waterfront Oasis: A Luxurious Family Retreat
10.0 out of 10, Exceptional, (41)
"The Hosts were extremely nice and helpful in the entire process. They answered questions and helped me understand the offering so I could book with confidence, The home is spacious and welcoming in design. Generous spaces throughout including a very nice kitchen and a basement gameroom that was very enjoyable. The outside seating areas were outstanding including a wonderful lakefront area to sit and enjoy the views. Book with confidence for a great experience. Dan and Kit "
Candlewood Lake Grand Waterfront Oasis: A Luxurious Family Retreat
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, (4)
"Main and only complaint was that had to keep playing with the handle of the toilet every time flushed or it would keep running. Very annoying. And just felt food items. ( pancake mix ect) should be tossed. Safety and health purposes . Otherwise very enjoyable. Stay"
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Aerial view
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
10.0 out of 10, Exceptional, (8)
"The hosts were wonderful and so welcoming. The house had everthing you could want and more! It was the perfect location for my family to relax before and get ready the day of my daughter's wedding. "
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Fridge, microwave, stovetop, dishwasher
Ashley Falls Home w/ Fire Pit: Hike & Ski!
9.6 out of 10, Exceptional, (11)
"The house was well appointed, clean, quiet and convenient.We hope to return in the future."
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Charming 1870 cape cottage in Litchfield
Outdoor dining
Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (38)
"Spent three nights at this cottage and enjoyed it very much. Beautiful area returned to after a long time. Definitely recommended. "
Charming 1870 cape cottage in Litchfield
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
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.
Don't see what you're looking for?
See all available properties in Litchfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Litchfield

Litchfield Hills Hideaway
Fridge, microwave, oven, stovetop
Litchfield Hills Hideaway
10.0 out of 10, Exceptional, (52)
"They did a great job of supplying everything we needed without junking it up. It was really centrally located on Rt 202. We came in for a HS reunion and it worked great! "
The price is AU$393
includes taxes & fees
17 Nov - 18 Nov
Litchfield Hills Hideaway
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, (14)
"This house does have a lovely view that allowed us to take in the changing leaves off the reflection of the lake. The house is smaller than it appears in the photos and not quite as comfortable to just hang out, at least inside.The couch fits three, but there aren't other chairs in the living area. There are great little outside areas though. Communication with Katherine was great. Previous tenants had broken the washer which was a drag and due to weather (drought conditions) we couldn't use...
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
On the beach, sun-loungers
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (73)
"Awesome stay!"
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
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.