Photo by Jennifer Magri

Search Vacation Homes in Litchfield

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 280 Vacation Homes in Litchfield with updated reviews, rates, and availability.

Lakefront Summer Spectacular in New England Just 2 Hours From NYC

9.8 out of 10, Exceptional, (69)
"The host was great and the property had everything we wanted and more. We will be back."
Lakefront Summer Spectacular in New England Just 2 Hours From NYC

Charming Connecticut Retreat Near Museums & Hiking

8.0 out of 10, Very Good, (3)
"We loved this place. It's an older house but the owner had done a wonderful job with restoration and upkeep. The yard was perfect for our large dog and the kitchen was cozy and inviting. We really enjoyed our stay and would definitely return on another trip to do it all over again."
Charming Connecticut Retreat Near Museums & Hiking

Connecticut Retreat: Steps to Historic Downtown!

9.6 out of 10, Exceptional, (13)
"Everything was as described and updated we enjoyed our stay. "
Connecticut Retreat: Steps to Historic Downtown!

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (25)
"This was a much needed haven! Frank was very helpful and hospitable. All of the animals were a definite plus! "
Mountaintop Horse Farm with Heated Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House

Peaceful Oasis in Naugatuck - Charming 3-Bedroom Home with serene backyard.

Peaceful Oasis in Naugatuck - Charming 3-Bedroom Home with serene backyard.

Mountain View Getaway

10.0 out of 10, Exceptional, (53)
"Such a magical place…always enjoy our stay. The home is so comfy - the hosts are amazing. "
Mountain View Getaway

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
The price is AED 368
AED 2,139 total
includes taxes & fees
2 Jun - 3 Jun
CT Gate House Goshen CT, Gate House Goshen CT

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

9.4 out of 10, Exceptional, (22)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

NEW-Another Fun Downtown Location 1st floor

2.0 star property
9.8 out of 10, Exceptional, (17)
"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

Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

10.0 out of 10, Exceptional, (9)
"We really enjoyed being able to stay at such a beautiful home. Between the animals and the hot tub view - the serenity will be hard to match elsewhere!"
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (24)
"Awesome location, plenty of space in the house, clean, and the host was very responsive. Will definitely stay here again when in Connecticut. "
Family House On Highland Lake with Dock

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (34)
"Went there for a weekend with a friend to hole up and relax in February and it was lovely. Listing is accurate and Cindy was very easy to communicate with. Hot tub was great!"
The Goshen Glass Chalet

Litchfield County Getaway

10.0 out of 10, Exceptional, (43)
"Property is a great getaway from a fast paced life. Quiet and beautiful. Open floor concept. Country living with all the update of the city. Very clean. "
Litchfield County Getaway

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (51)
"Property was great and the owners thought of everything. Instructions were clear and helpful! Didn’t want for a thing, such a lovely space to spend a few days and so close to Litchfield and Bantam shops and restaurants. We loved it!! "
Charming 1870 cape cottage in Litchfield

Make lifelong memories at this New England Quintessential Country Getaway

10.0 out of 10, Exceptional, (40)
"We headed back to my hometown just surprise my parents with a visit from their grandchildren and great grandchildren."
Make lifelong memories at this New England Quintessential Country Getaway

#26 Beautifully Renovated 2 BR Home

10.0 out of 10, Exceptional, (1)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
The price is AED 536
AED 998 total
includes taxes & fees
17 Jun - 18 Jun
#26 Beautifully Renovated 2 BR Home

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

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (13)
"Great property close to all kinds of places to visit and scenic nature!"
The price is AED 826
AED 1,174 total
includes taxes & fees
2 Jun - 3 Jun
Tranquil Litchfield Connecticut Retreat".

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

9.6 out of 10, Exceptional, (85)
"We had an amazing time. The house was beautiful and clean and communication between us and the hosts was wonderful. We would love to stay there again!"
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.
Save an average of 15% on thousands of hotels when you're signed in