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Compare 215 Vacation Homes in Litchfield with updated reviews, rates, and availability.

Renovated, one level home in an excellent location
Fully equipped kitchen. (1)

Renovated, one level home in an excellent location

10.0 out of 10, Exceptional, (38)
"3 college roommates stayed because new Milford was a convenient location for all 3 of us. Great girls trip catching up with wine snacks and movies. We weren’t familiar with the area so wished we would have stayed closer to town aka the Green but it was nice to have a 5 minute walk down to the little private beach area and an easy 10ish minute drive to town to walk around some shops before heading back to enjoy good company. Thanks Alberto! U were great with ur communication both before and...
Renovated, one level home in an excellent location
Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (77)
"Thank you for allowing us to reside at your beautiful property. We appreciate your expedited communication & commitment to quality. We thank Jehovah for a safe enjoyable trip & as we return back to Atlanta, GA. "
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Charming 1870 cape cottage in Litchfield
Outdoor dining

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (40)
"Beautiful property. Super clean. Wish we could have stayed longer."
Charming 1870 cape cottage in Litchfield
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
Exterior detail

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

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

Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
The Candlewood Lake Retreat - Private Dock & Pool

The Candlewood Lake Retreat - Private Dock & Pool

The Candlewood Lake Retreat - Private Dock & Pool
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
Exterior

Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!

10.0 out of 10, Exceptional, (11)
"This was just what we were looking for. The house was roomy, open and charming. It was also relaxing to sit on the back deck surrounded by trees and listening to the calming sound of the brook. It felt like you out in the countryside yet the cute village of Sandy Hook along with Newtown restaurants and shopping were less than 10 minutes away."
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Living Room

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

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

9.0 out of 10, Wonderful, (6)
"We had a wonderful time. Quiet and pleasant "
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Cozy Litchfield House w/ Fenced-In Yard & Fire Pit
Litchfield Vacation Rental | 3BR | 2BA | 1,500 Sq Ft | Stairs Required

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
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Salisbury Vacation Rental | 6BR | 3.5BA | 2,525 Sq Ft | 2 Steps to Enter

Serene Salisbury Rental Home on 26 Acres w/ Deck!

9.8 out of 10, Exceptional, (7)
"Great weekend getaway with family to celebrate "
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Bluebird Valley Farmhouse
Property grounds

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
Stylish & Luxurious 3 BDR Home with Play Station
Living area

Stylish & Luxurious 3 BDR Home with Play Station

9.8 out of 10, Exceptional, (7)
"We had an issue getting into the house, but the host answered the phone immediately and helped us gain access. His communication was excellent. We chose this location because of the proximity to our family and it worked out perfectly."
Stylish & Luxurious 3 BDR Home with Play Station
Enjoy a getaway on the scenic Housatonic River/Lake Lilinonah in New Milford, CT
Miscellaneous

Enjoy a getaway on the scenic Housatonic River/Lake Lilinonah in New Milford, CT

9.0 out of 10, Wonderful, (6)
"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
Majestic Mountain Side Sheffield/Great Barrington/SKI
30 ft ceilings with huge dining area

Majestic Mountain Side Sheffield/Great Barrington/SKI

Majestic Mountain Side Sheffield/Great Barrington/SKI
Relax or be active! The choice is yours in this pet-friendly family home.
Our Home

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

9.8 out of 10, Exceptional, (10)
"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.
Perfection in Litchfield County
Living area

Perfection in Litchfield County

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was well maintained and the decor of the home was thoughtful and creative. Enjoyed using the fireplace and cooking meals in a fully stocked kitchen. The house had plenty of room for all of us. Each room has a TV and really comfy beds. "
Perfection in Litchfield County
COUNTRY RETREAT WITH POOL 10 MN FROM KENT CT
house

COUNTRY RETREAT WITH POOL 10 MN FROM KENT CT

10.0 out of 10, Exceptional, (4)
"Our family of five (three grown children) needed our own place for Thanksgiving weekend as our Thanksgiving hosts in Kent had a full house with their family. The home is not "super large" but it has nice, comfortable space spread out on one floor; it is immaculate, sunny, high on a hill with a pleasant view east. Primary bedroom has very comfortable bedding with a modern bath. Pool was closed but in it's own world below the house. The attractive, "happy" kitchen was filled with all the...
COUNTRY RETREAT WITH POOL 10 MN FROM KENT CT
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
Living area

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (54)
"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 SAR 563
SAR 961 total
includes taxes & fees
30 Dec - 31 Dec
Litchfield Hills Hideaway
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (77)
"Thank you for allowing us to reside at your beautiful property. We appreciate your expedited communication & commitment to quality. We thank Jehovah for a safe enjoyable trip & as we return back to Atlanta, GA. "
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
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.