
House holiday rentals in Litchfield
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Top-rated house rentals in Litchfield
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Popular amenities for house rentals in Litchfield
House rentals with a pool

Beautiful Country Farmhouse w/ Pool
This is a beautiful, cozy and tasteful home. We loved the contrast between the original 300 year old farm beautifully maintained and renovated and the newer rooms. Kitchen was great and the fireplace worked wonderfully. Wifi and office space were perfect to get a few hours of work done. Had a great week skiing in nearby Mohawk and visiting Litchfield and Bantam. It was useful to inquire about the lay out and steep stairs. Daire was super responsive and helpful throughout our stay. We had a wonderful time. Thanks for sharing your home!

Pool House
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

Amazing Oasis Private Pool, BBQ, Pool Table.
Glenda was friendly and had great communication from Start to Finish. This was a nice location for a family fun weekend. Although the drive is close enough to stores if you need anything (target/stopnshop/bjs etc), the property is in a quiet and safe neighborhood. The yard is a great place to hang out and relax with the fire pit or have fun in the pool. And when the weather was crappy the pool table and hanging out in the basement den was nice. Everything in the house is labeled and easy to find. We enjoyed the space and would definitely recommend. Thanks again! 😊

Garden Level Suite with Beautiful Pool
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Bright Mid-Century Modern Retreat-90 min from NYC
My family and I had a wonderful weekend at the house. The house is beautiful and was extremely clean when we arrived. Luiz kindly left a sled for my kids to use in the yard. There is plenty of outdoor space and the yard has a good deal of privacy. There are two bedrooms and a den/office with a TV. The kitchen has everything we needed. Luiz was very easy to communicate with.

Meeker Hill House - Country Escape w/ Heated Pool
Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend

Country retreat on 4 private acres
My family and I had such a wonderful time. The home and the surroundings were so beautiful, peaceful, quiet, and relaxing. Everything was very clean, and the bed and pillows were so comfortable. My toddler especially enjoyed the cute bathtub in the master bedroom. The pool was beautiful, just wished we were there when the weather was nicer, as the water was quite cold. The restaurants nearby (10 mins away) were so good, we especially loved everything from a place called Kingsley Tavern. Overall, loved our stay and would definitely stay here again!

Woodland Country Retreat-Pool+FirePit-nearWineries
Thank you for a lovely visit. We were in Litchfield with two other couples to go to a wedding. The house was perfect for us. The house had everything we needed. Two of the four rooms only have twin beds but we didn’t mind. I only wish the weather was warmer so we could use the pool!
Weekly house rentals

Gunn Brook Mountain House
My family and I had a lovely stay at Rebecca’s house. It was so private and peaceful. Bird and brook sounds filled the air. The house was as serene as the surroundings, with plenty of comfortable furnishings and a great flow. This part of Connecticut was new to me, and it did not disappoint with plenty of rural beauty. We only just began to explore it. The second my family entered the house they begged for a longer stay! I wish we could have stayed longer — we’ll be back.

Magical Woodland Getaway
Lovely home, beautifully decorated, in great country setting with easy access to neighboring towns. Our host was very responsive.

Private Woodland Sanctuary—3 mins to a lake beach!
this place is magical. my sisters and I have stayed here twice now, for her wedding and now for mine. both times the home has been clean and the overall experience has been wonderful.

UB’s Corner
Our stay at Ellen’s Lake House was perfect. It was comfortable, clean and the view of the lake is amazing. My husband enjoyed fishing and we both loved being on the water. Ellen was helpful and made our stay a wonderful experience.

Serenity in the Roxbury Woods!
We enjoyed a wonderful stay! Danny was truly amazing! Very responsive and even checked on us during the winter storm to ensure everything was ok. He also had the snow plow come through and do the driveway prior to checkout. The house is amazing and we can’t recommend Danny’s place enough!

Carriage House on Smith Pond!
By far one of the nicest air B&B’s we’ve stayed in. Beautifully renovated carriage house on an incredible piece of property. Todd and Janet warmly welcomed us with their chickens’ fresh eggs, fruit and muffins. Kitchen was well equipped for preparing meals and we enjoyed dining al fresco while hawks flew and deer ran across the fields. Upstairs is a comfortable bed with nice linens and a large bathroom. This is a real gem! We hope to return in the future.

The Main Farmhouse at Gray Rock Farm
Jim and Phoebe's place worked perfectly for our family. Old world charm with updated amenities provided an oasis during the whirlwind of our nephews' graduation party/family reunion. Thanks for also encouraging the music! I've always wished houses would have musical instruments, and Jim and Phoebe had a piano, guitar, and mandolin. I dusted-off a couple of 80's power ballads with the Epiphone. Reinvigorating and recharging, Thanks!

Historic Charm
This is a historical house, updated for modern expectations. Kitchen is beautiful, baths are redone and clean. Historical touches are preserved - beautiful staircase and wood floors from the 1800s. The house matches the description, and is comfortable. Susan, the host has her communication levels just right- will make sure you have everything you need, and will respond quickly. Thank you so much!
Private house rentals

Bantam Beauty: Surrounded By Nature!
Ronni's place was wonderful! Very spacious for a group of 10 adults. Due to storms overnight the night before our arrival, Internet was knocked out and could not be immediately repaired. Ronnie reached out before we arrived to let us know and to offer a fair adjustment due to the missing amenity. we would definitely stay again if in the area.

Don’t miss out on this cozy escape! w/Skatepark
Shawn created a special place here. Love all the details, especially the skateboards and music room. The hot tub was lovely after a long day of driving, I soaked again in the morning. ColecoVision console in the game room was so nostalgic along with a great selection of other games. I really enjoyed the grounds. Even wandered down to the dam/waterfall. My mother in law, son and wife all had their own space to stretch out. I could easily spend more time here, it is not just a place to lay your head for the night.

Jim & Pat’s Litchfield Hills Lookout on 4.3 acres
The house was spotless and comfortable. Unfortunately, to no fault of the host, power was lost for 2 hours on Saturday. It only posed a problem because 5 people were trying to get ready to attend a wedding at Winvian during that time! The other hiccup was that my granddaughter came to visit while her parents were at Winvian preparing for her uncle's wedding. The listing mentioned baby items, such as a crib, high chair, toys, etc. We couldn't find them. Maybe you have to request them to be able to use them? We made due but it just added an extra challenge. The house is very close to Winvian and was very helpful for going back and forth between the 2 places. As a previous review mentioned, the driveway situation is a bit precarious but in the end, it wasn't as difficult as it first appeared. If I found myself in that area again, I would definitely book it.

The Wildflower House
Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!

Beautiful sun filled cottage in the woods
We hosted a Friendsgiving here and it was so lovely. From the falling snow to the open concept, it was a wonderful gathering abode for the holiday. Thank you!

The Art House: 5-Acre Getaway w/ AC & Firepit
My family and I stayed at this Airbnb during my wedding weekend and it was perfect! The house is beautiful. It had one bedroom and bath downstairs for my grandma to stay in so she didn’t need to go up the stairs. The kitchen is amazing! It was a great distance to the Candlewood Inn where we got married. Jessica was very responsive and always checking in. Would definitely stay here again!

A peaceful & sophisticated country retreat
Justin’s place was perfect, I highly recommend it, especially if you are in the area to visit a child a one of the nearby schools. It was so clean, peaceful, and Justin was a great host. Thank you!!!!

Direct Waterfront with Private Beach - Entire Home
I grew up on lake harwinton and the lake is just as peaceful and wonderful as I remember. The house was a great find. It was totally stocked with everything one could ever need. That includes firewood and fire starter for the fire pit outside. I did not realize that, and brought my own, but what a great touch! Some airbnbs don't provide firewood. All in all, this Airbnb was perfect. Lawrence and Denise communicated everything very clearly and were quick to respond if I had a question.
Quick stats about house rentals in Litchfield
Total rentals
80 properties
Nightly prices starting at
$116Â SGD before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool
Destinations to explore
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- Fairfield Beach
- Yale University
- Six Flags New England
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Woodmont Beach
- Seaside Beach
- Jennings Beach
- Silver Sands Beach
- Bushnell Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Calf Pasture Beach
- Kent Falls State Park
- Wildemere Beach
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Clinton Town Beach
- Sherwood Island State Park
- Bayview Beach
- Hudson Highlands State Park
- Brownstone Adventure Sports Park
- Anchor Beach