House vacation rentals in Litchfield

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Popular amenities for Litchfield house rentals

House rentals with a pool

Guest favourite
Home in Stanfordville
4.96 out of 5 average rating, 48 reviews

Charming lakeside cabin with private heated pool

JustinRating, 5 stars8 months ago
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!
Guest favourite
Home in Woodbury
4.94 out of 5 average rating, 18 reviews

2 homes in one (in-law design) w/salt water pool

ChristineRating, 5 stars7 months ago
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!!
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 133 reviews

Pool House

EllenRating, 5 stars3 weeks ago
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.
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 months ago
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!
Guest favourite
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars2 months ago
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.
Superhost
Home in Stanfordville
5 out of 5 average rating, 5 reviews

The Round House w/ Heated Pool

JonathanRating, 5 stars5 months ago
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.
Top guest favourite
Home in Roxbury
5 out of 5 average rating, 17 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

SidRating, 5 stars2 months ago
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.
Superhost
Home in Litchfield
4.9 out of 5 average rating, 49 reviews

Woodland Country Retreat-Pool+FirePit-nearWineries

Sarah & SteveRating, 5 stars6 months ago
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

Superhost
Home in Westbrook
4.86 out of 5 average rating, 194 reviews

Family-Friendly Cottage by The Shore

TristanRating, 5 stars1 week ago
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!
Guest favourite
Home in Hudson
4.92 out of 5 average rating, 202 reviews

Hudson New York Grey Victorian

KarlaRating, 5 stars2 months ago
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!
Guest favourite
Home in Garrison
4.93 out of 5 average rating, 161 reviews

Hudson Valley Mountaintop Riverview

ChristopherRating, 5 stars4 weeks ago
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!
Superhost
Home in Ancram
4.8 out of 5 average rating, 112 reviews

Secluded Post-And-Beam Retreat

SarahRating, 5 stars2 months ago
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.
Guest favourite
Home in New Britain
4.9 out of 5 average rating, 106 reviews

5•Star CapeCodStyle Gem with a Bedroom on the Main

GregRating, 5 stars1 day ago
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!
Guest favourite
Home in Madison
4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

GretchenRating, 5 stars6 months ago
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.
Guest favourite
Home in East Hampton
4.92 out of 5 average rating, 93 reviews

Clean private home near Lake Pocotopaug!

CathyRating, 5 stars4 months ago
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!
Superhost
Home in Clinton
4.71 out of 5 average rating, 90 reviews

Year-Round Waterview 4 Bds/2Bths, Sleeps 13 Linens

MaryRating, 5 stars6 days ago
This house was very good for me and my friends and we would love to go back!

Private house rentals

Top guest favourite
Home in Egremont
4.96 out of 5 average rating, 120 reviews

The Berkshires Mountain Terrace LUX Home Sleeps 7

CourtneyRating, 5 stars2 months ago
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.
Guest favourite
Home in Chester
4.98 out of 5 average rating, 209 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

TimRating, 5 stars6 months ago
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.
Guest favourite
Home in Monterey
4.97 out of 5 average rating, 34 reviews

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

GallianeRating, 5 stars2 months ago
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.
Guest favourite
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars3 weeks ago
It was wonderful stay and I’d go back anytime
Guest favourite
Home in Colebrook
4.96 out of 5 average rating, 74 reviews

Log Cabin sleeps 30 bunk style on 350 acres

RomaricRating, 5 stars8 months ago
Beautiful time, we can't wait to come again.
Guest favourite
Home in Warren
4.94 out of 5 average rating, 108 reviews

Litchfield County Getaway

DemianRating, 5 stars5 months ago
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
Top guest favourite
Home in Catskill
4.95 out of 5 average rating, 154 reviews

Best of Both Worlds! Nature in the Village!

JeaniaRating, 5 stars4 months ago
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!
Guest favourite
Home in Craryville
4.92 out of 5 average rating, 113 reviews

The Gatehouse at Raspberry Ridge

JenniferRating, 5 stars1 week ago
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

Destinations to explore