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

Charming lakeside cabin with private heated pool
My family and I stayed for a long weekend and were so glad that we did! It’s a beautiful cabin, with all the things you need. Kitchen is stocked with essentials, enough bathrooms, beds are super comfortable, hooks to actually hang things like towels, jackets… but we loved the outdoors even more! We walked to the lake, spent way too many hours in the pool, grilled, lounged, made s’mores by the fire pit and watched the beautiful stars at night. Couldn’t ask for more. Paula and her lovely family are SO welcoming it’s crazy. 😂. Hope to be back next summer!

2 homes in one (in-law design) w/salt water pool
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!

Pool House
Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.

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!

Hilltop House w/POOL/SPA- HOST & Co.
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.

The Round House w/ Heated Pool
An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.

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.

Woodland Country Retreat-Pool+FirePit-nearWineries
Jean was extremely friendly to let us book a last-minute stay at this home the day prior. The home is in a good location and has a nice layout, although we were only three people and did not use all of the house. One thing to note is that the heat was restricted to 70° and 72° depending on the thermostat and my elderly parents from Florida were extremely cold the entire weekend, wearing jackets and warm hats the round the clock even inside during their visit. Sadly for our group, the foliage of Fall had all disappeared save for one tree. Also, the pool was not available so we cannot comment on this. All in all, a lovely home, but definitely priced quite high, considering.
Weekly house rentals

Family-Friendly Cottage by The Shore
I had a nice, overnight stay at Marie's place. All was as described and the instructions for everything were spot on. Comfortable & convenient stay, would visit again!

Hudson New York Grey Victorian
This house was perfect for our girls’ weekend in Hudson! It was spacious, clean, and had so much character. The location was great—just a short 5-minute drive to Warren Street. We didn’t walk due to the cold weather but it was definitely close and convenient. Would definitely stay here again!

Hudson Valley Mountaintop Riverview
Mahmoud's accommodation was more than we could have wished for, it was perfect and had the most incredible views of the Hudson River and surrounding mountains. Mahmoud was very responsive and was able to answer all of our questions and fulfill our requests. We highly recommend his home to anyone else that's interested and we would love to make a trip back sometime in the future!

Secluded Post-And-Beam Retreat
A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.

5•Star CapeCodStyle Gem with a Bedroom on the Main
We had a great stay at Chana’s place. She was very easy to communicate with and the house was comfortable and very clean. We’d love to stay again next time we’re in CT!

Historic Beachside Glamour
A lovely cottage on a quiet street (at least in the fall!). The interior is just beautiful with all the wood floors, walls, ceilings. The kitchen was - unusual! Clearly they had to retrofit an old home to accommodate modern appliances, but all worked well.

Clean private home near Lake Pocotopaug!
I highly recommend this property. It was perfect for our Christmas visit with family. The furniture and beds were very comfortable. We truly enjoyed our stay in East Hampton. We will be back!

Year-Round Waterview 4 Bds/2Bths, Sleeps 13 Linens
This house was very good for me and my friends and we would love to go back!
Private house rentals

The Berkshires Mountain Terrace LUX Home Sleeps 7
This was a beautiful and well kept home and was a delight to stay in. Natalia was also a lovely and communicative host. We had no issues and would happily stay there again.

Stunning Artisan Waterfall Escape, Walk Downtown
We'd been looking forward to coming back to The Recycle House since we first stayed there in 2022. Safe to say it was just as we remembered it...great house, great location, wonderful community. Looking forwarded to returning.

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.

Welcome To Piper's Rest
It was wonderful stay and I’d go back anytime

Log Cabin sleeps 30 bunk style on 350 acres
Beautiful time, we can't wait to come again.

Litchfield County Getaway
Was in the area to visit family and this was a perfect location for me. Had just what my family needed to have a great weekend

Best of Both Worlds! Nature in the Village!
We had an absolutely wonderful stay at this Airbnb! From the moment we arrived, the host was incredibly welcoming and made sure we had everything we needed for a comfortable stay. The space was clean, cozy, and beautifully decorated, with thoughtful touches throughout. The location was perfect—quiet yet conveniently located. I would highly recommend this place for anyone looking for a relaxing and enjoyable getaway!

The Gatehouse at Raspberry Ridge
If your looking for a great quiet stay while visiting Hudson or other local places this home is it. Very clean, super dog friendly. Close to the highways and hidden enough to really be apart of nature.
Quick stats about house rentals in Litchfield
Total rentals
80 properties
Nightly prices starting at
$124 CAD 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
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- Fairfield Beach
- Yale University
- Catamount Mountain Ski Resort
- Six Flags New England
- Walnut Public Beach
- Woodmont Beach
- Seaside Beach
- TPC River Highlands
- Clinton Town Beach
- Jennings Beach
- Taconic State Park
- Marvin Beach
- Anchor Beach
- Walkway Over the Hudson State Historic Park
- Bushnell Park
- Thunder Ridge Ski Area
- Calf Pasture Beach
- Bayview Beach
- Clinton Beach
- Mohawk Mountain Ski Area
- Sherwood Island State Park
- The Connecticut Golf Club
- Southport Beach
- Wildemere Beach