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

Private Hudson Valley Country Retreat
We were absolutely charmed by this stunning house, surrounded by breathtaking nature and offering incredible views—especially over the lake. Every corner is filled with character and warmth, making it feel like a true hidden gem. A huge thank-you to our wonderful host Sandy, who was incredibly thoughtful and proactive throughout our stay. We couldn’t have asked for a better experience. We’ll be back without a doubt!

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!

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!

4Br Mountain Brook House on 130 acres w/ trails
We were 5 girlfriends staying at this property. Each one of us loved everything about it . Perfect location !

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!

Litchfield Hills Lakefront Getaway! Amazing Views
Great stay on the lake! Host provided plenty of great boating and lake equipment, which we used often. Bbq and fire pits were fun, plus there is a covered section for when it rained. Amazing family spot!

Hilltop modern with stunning mountain views
The house was beautiful and very family friendly. They greeted us with milk, orange juice and a carton of eggs in the fridge. They even had a selection of beer testers for my husband to try. We had an issue with the pool heater not turning on and both host were very helpful and responsive. I loved the hand drawn map guide they made me when I could not locate something ! They even got someone out there that same evening. Especially on Memorial Day weekend I was impressed on how quickly. I would definitely recommend this home to anybody and will go back if I’m ever in the area again.
Weekly house rentals

The Barn - Rustic Chic Loft, Hotchkiss, Lakes, Ski
Very comfortable house - nice and airy. Great location just outside Lakeville. Highly recommend.

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.

Artist's Retreat In The Woods | Five-Acre Backyard
What a fabulous home! My family had a peaceful and enjoyable stay at this hidden gem! The home is spotless and has everything you need to feel at home, sleep well and cook! Thank you to a superb host!!

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!

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.

4 Bedroom Home Tucked Away in Litchfield Hills
My wife, our two kids, and our friends who also have kids had a spectacular time staying at Lindsey's over Memorial Day Weekend. We booked last minute but were very pleasantly surprised at how much fun we ended up having in the area as well as Lindsey's place in particular. It's a beautiful house, immaculately kept, easy check in and check out, with absolutely everything we could possibly have needed. There were all kinds of really fun activities for the kids and us both at the house and in the surrounding neighborhoods which made our stay memorable. We'd highly recommend this spot for anyone, especially with kids, looking for a weekend or longer getaway. Thanks so much, Lindsey!

Spacious Country Comfort
Thank you for letting us stay at your place! It worked out so well and we appreciate having all the space.
Private house rentals

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!

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
Such a great spot. Perfect size for a couple. Everything is really nicely laid out and we were especially thankful for how well stocked the kitchen came. Really beautiful view out the huge front windows. Also, super comfortable bed :)

Quiet and Cozy Getaway
We came in for a bridal shower. I 100% recommended to other out of towners this listing. Wanted to stay a few more days but our schedules wouldnt allow. It is definitely worth the 5 star review!! Will be staying here in the future to visit my sister less then 2 miles away!!

Charming Home in Litchfield County on a MAIN ROAD!
Perfect placement, central to our needs. I love the fact my dog didn't have to be in a crate while we were out. I also love that there were laundry and dishwasher pods. Fantastic stay overall.

Bright Mid-Century Modern Retreat-90 min from NYC
We had a wonderful stay. The house was clean, and comfortable, and exactly as described. The location was peaceful and beautiful — perfect for relaxing and spending time in nature. The host was responsive and thoughtful. We’d definitely love to come back!

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.
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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
- Sherwood Island State Park
- Bayview Beach
- Hudson Highlands State Park
- Brownstone Adventure Sports Park
- Anchor Beach
- South Pine Creek Beach