Photo by Sanka Perera

Search Vacation Homes in Litchfield Historic District

  • 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

Compare 155 Vacation Homes in Litchfield Historic District 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
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
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
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
An acclaimed photographers country estate, arts community, near private schools!
Fair Rising: our beautiful country estate!

An acclaimed photographers country estate, arts community, near private schools!

9.6 out of 10, Exceptional, (19)
"ALL FACILITIES WERE GREAT EXCEPT INTERNET. Very CLOSE TO MILLBROOK HT. THE HOME WAS VERY NICELY EQUIPED. AL THE BEDS VWERE EXTREMELY CONFORTABLE, KITCHEN WAS WELL EQUIPPED. WE WOULD STAY THERE AGAIN"
An acclaimed photographers country estate, arts community, near private schools!
Spacious Home nestled along the Blackberry River in Northwest CT
Exterior

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (80)
"This was the second time I stayed here with my curling team. 3 nights, playing in a tournament at the nearby club. The house is extremely comfortable. Jennifer is very prompt and very friendly with her responses to my questions. No issues whatsoever."
Spacious Home nestled along the Blackberry River in Northwest CT
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
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
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
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
3-bedroom house in fantastic Sharon with WiFi, overlooking nature preserve
Exterior

3-bedroom house in fantastic Sharon with WiFi, overlooking nature preserve

2.0 star property
3-bedroom house in fantastic Sharon with WiFi, overlooking nature preserve
3-Bedroom Cabin Getaway With Rustic Charm
Terrace/patio

3-Bedroom Cabin Getaway With Rustic Charm

6.0 out of 10, (1)
3-Bedroom Cabin Getaway With Rustic Charm
Charming 3-bedroom house in Waterbury with WiFi, AC
Room

Charming 3-bedroom house in Waterbury with WiFi, AC

Charming 3-bedroom house in Waterbury with WiFi, AC
Hat Shop House: Charming Retreat in the Heart of New England. Family friendly.
Living area

Hat Shop House: Charming Retreat in the Heart of New England. Family friendly.

10.0 out of 10, Exceptional, (5)
"We had such a great time at this property and the surroundings area. Owners truly made everything possible for one to enjoy the weekend, take all the planning/ research away. So much was provided in the house/ everything you need! So much helpful resources/ suggestions! Thank you!! Place is especially great with kids- toys, playground, books. But our grandparents enjoyed it equally as much. No one wanted to leave. Owners were available in seconds should any questions come up. What a beautiful...
Hat Shop House: Charming Retreat in the Heart of New England. Family friendly.
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
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Property grounds

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

9.8 out of 10, Exceptional, (21)
"Gorgeous home and property, loved being on the lake with the game room cabana, the outdoor areas are so relaxing, and the home is so tastefully decorated. We enjoyed it so much!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Tranquil Litchfield Connecticut Retreat".
Terrace/patio

Tranquil Litchfield Connecticut Retreat".

9.4 out of 10, Exceptional, (8)
"Perfect location for visiting family in the area. Close to restaurants, grocery stores and other amenties. Simple place with everything you need to make visiting family plessurable. The washer and dryer will remind me to pack much less next time. Jose was a grear jost. On top of any questions and responded within the hour. Thank you for allowing us into your property. Shane share "
The price is SAR 827
SAR 1,186 total
includes taxes & fees
17 Jan - 18 January 2025
Tranquil Litchfield Connecticut Retreat".
Private hidden gem walking distance to town, restaurants, and shopping!
Exterior

Private hidden gem walking distance to town, restaurants, and shopping!

9.8 out of 10, Exceptional, (14)
"It was very nice and relaxing . Close to everything. "
Private hidden gem walking distance to town, restaurants, and shopping!
Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce
Living area

Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce

9.8 out of 10, Exceptional, (6)
"A family member and I were "
Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce
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 Historic District
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 Historic District

Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (17)
"great chic house, very clean"
Cozy & Chic Cabin by the Lake, with access to private Beach!
TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX
Room

TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX

9.8 out of 10, Exceptional, (18)
"My stay here was amazing.Very clean.Very welcoming with a forever homely feel.The communication with the property owner/manager was great and very helpful with everything.When i return to Connecticut,I will be looking forward to returning to this rental and also recommending to family and friends if traveling to the area.5*"
TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Fall sunsets are a prize possession here at the lake!

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (27)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
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.