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House holiday rentals in Litchfield County

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Popular amenities for house rentals in Litchfield County

House rentals with a pool

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!!
Superhost
Home in Millerton
4.88 out of 5 average rating, 25 reviews

Farmhouse with a view, hot tub, pool, and fire pit

BrittanyRating, 5 stars5 days ago
The house and the property were absolutely beautiful. We are already thinking of coming back in the summer while the pool is open for longer than a weekend! highly recommend 👌
Guest favourite
Home in New Milford
4.95 out of 5 average rating, 21 reviews

Spacious and relaxing New Milford 5br home w pool!

ElizabethRating, 5 stars5 months ago
Jarret was extremely helpful and friendly. The house was exactly what we needed. I will definitely come back and stay here next time I’m in town.
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.
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.
Top guest favourite
Home in Kent
4.96 out of 5 average rating, 26 reviews

Country retreat on 4 private acres

CaseyRating, 5 stars5 days ago
We sought out a quiet and peaceful place we could stay after a long winter. We got exactly that with Monica's home in Kent, Connecticut. We traveled with two dogs and our toddler. This home was able to accommodate that. Our toddler has a lot of energy and seeking out a place where we could get all of his energy out but still maintain a peaceful atmosphere, so we thought, would be hard. But tucked away in the beautiful forest of Kent, we found a place where our toddler could run through the large property and he had plenty of activities inside as well. Monica had everything equipped for families with children. Due to weather, the internet went out the day before we were to check out and unfortunately remained that way the remainder of the trip. But Monica was quick to inform me and we were able to find plenty of activities to do in the home. We truly appreciated all the amenities that this home had to offer for a peaceful and relaxing stay.
Guest favourite
Home in Bethlehem
5 out of 5 average rating, 45 reviews

Lakeview Expanse

ElodieRating, 5 stars1 month ago
Our stay at Kartik's very charming house was nothing short of amazing. From the moment we arrived, we felt warmly welcomed. The house itself is beautifully decorated, blending comfort and character effortlessly. The location was perfect- peaceful yet conveniently close to many trails, activities in Bethlehem (great indoor flea market) and Bantam lake. We especially loved hanging in the living room close to the fireplace watching the scenic views. Kartik was an exceptional host, responsive, kind and full of great recommendations. Thank you, the whole family had a blast!
Guest favourite
Home in Litchfield
4.94 out of 5 average rating, 16 reviews

Iconic Litchfield Home in Town Center

ClareRating, 5 stars5 months ago
The house was beautiful! We loved the charm of the old floors and the cozy farm style. The house was so clean, we all noticed and appreciated the time it must have taken to clean. Thank you for a wonderful stay!

Weekly house rentals

Guest favourite
Home in Watertown
4.91 out of 5 average rating, 53 reviews

Tiny Home Away From Home - Complete Privacy, Peace

MarceloRating, 5 stars3 weeks ago
Great place and location, had to get something for a couple of days to get away from the city. Enjoyed my stay and would indeed go back again !
Top guest favourite
Home in Salisbury
4.98 out of 5 average rating, 65 reviews

Curated Contemporary for lakes, forest & ski hills

EricRating, 5 stars1 month ago
My family and I had an amazing few days at what is one of the most comfortable and beautiful environments. The house is loaded with everything you need and the surroundings were super cool. I will definitely be returning.
Guest favourite
Home in Sharon
4.93 out of 5 average rating, 185 reviews

Charming CT Country Farmhouse for group getaway

ChrisRating, 5 stars5 days ago
Such a fun old home, reminded my wife of the old farmhouse she grew up in. The location was perfect for our needs and there was enough space for everyone.
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 Brookfield
4.83 out of 5 average rating, 23 reviews

Lake Candlewood Retreat

FabioRating, 5 stars5 months ago
Nice place .. host is very responsive and helpful and place is nice .. beautiful lake views .. spent 30 days while renovating my house Nd was a smooth stay..
Superhost
Home in Watertown
4.8 out of 5 average rating, 40 reviews

Cozy Cottage

ToddRating, 5 stars1 week ago
The cottage was just as described and what you see in the photos is what you get. Hector was very responsive when I reached out to him. It was very comfortable and clean. Looking forward to being back and shared the listing with friends and family.
Superhost
Home in Bristol
4.74 out of 5 average rating, 54 reviews

Modern Homey Heaven | Garden view, Patio, Games

ShannonRating, 5 stars1 week ago
I had a great stay! Everything was just like the photos! Neighborhood is very safe and quiet. Felt right at home. Would definitely stay there again.
Guest favourite
Home in Sharon
4.92 out of 5 average rating, 151 reviews

Last Min. Special! Nature Cottage w/ River Access

FaithRating, 5 stars2 months ago
We enjoyed a lovely snowy weekend hiking, eating at local restaurants and curling up by the fire. This looks like a great place to return to during the summer for enjoying the outdoor amenities as well!

Private house rentals

Guest favourite
Home in Southbury
4.9 out of 5 average rating, 21 reviews

Cozy Family and Pet friendly 3 br Home

JennaRating, 5 stars5 months ago
We stayed at Ryan's place while visiting family in the area over the holiday weekend. The place was comfortable and clean and the bonus of being able to bring our pups was the best part. The dog park down the road was amazing and the locals were very friendly. The location was great, very convenient to shops, grocery store, gas etc. Overall we had a great time. Thanks again, Ryan!
Guest favourite
Home in Roxbury
4.95 out of 5 average rating, 43 reviews

Artist's Retreat In The Woods | Five-Acre Backyard

KimRating, 5 stars2 weeks ago
This was our second time staying at the Artist Retreat! It felt like we were going home! It is a beautiful spot and looking forward to returning in the fall!
Top guest favourite
Home in New Fairfield
5 out of 5 average rating, 28 reviews

Direct Lake Access - Priv Dock, Kayaks, EV Charger

PriscilaRating, 5 stars2 weeks ago
The house was exactly as listed. Our group was two adults and 3 kids. The kitchen had what we needed to cook meals, bake cookies and make milkshakes. The beds were comfy. The showers were hot with good water pressure for all. We would stay here again!
Top guest favourite
Home in Sherman
5 out of 5 average rating, 88 reviews

Slice of Paradise in the Country

AmoryRating, 5 stars1 week ago
This place is even better than the photos! Wow. It felt luxurious. Such a beautiful home. I loved all the snacks Deborah left us and the thoughtful touches (chocolates and water bottles next to the bed). So incredibly kind and very appreciated. This is definitely the best AirBnB I have ever stayed in. One “tip,” if you are someone who is used to sleeping in a dark room, then bring an eye mask because the primary bedroom has the most gorgeous window behind the bed and two magnificent skylights above the bed, but there aren’t blinds/shades. So the room is very bright. I would definitely love to go back (and bring my eye mask). Haha. Everything is so nice, the place is SPOTLESS, and the home feels very “new.” I just loved it. Also, Deborah has the NBA channel, which my son is obsessed with watching. This is just the best house - beautiful and pristine, yet cozy. Way nicer than most hotels. I loved the house so much! I loved the shampoo, the fluffy robes, the kids toys, everything!
Guest favourite
Home in Bridgewater
5 out of 5 average rating, 30 reviews

The Art House: 5-Acre Private Getaway w/ Fireplace

AlexandraRating, 5 stars2 weeks ago
We had a lovely stay at Jon's home with our two children. the snacks and coffee provided were a thoughtful touch and very welcoming. We had plenty of space in the home and enjoyed exploring the nearby towns.
Superhost
Home in Torrington
4.89 out of 5 average rating, 93 reviews

Charming Home in Litchfield County on a MAIN ROAD!

KatieRating, 5 stars3 weeks ago
We had a great stay! Everything was exactly as described in the listing. Would definitely stay again!
Guest favourite
Home in Winchester
4.88 out of 5 average rating, 26 reviews

Winchester House with wifi/high speed internet.

NedzadRating, 5 stars5 months ago
I would definitely go back to Krissie’s place again, highly recommended!
Guest favourite
Home in Southington
4.95 out of 5 average rating, 114 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

LindsayRating, 5 stars1 week ago
Every part of this house was beautiful, as was the huge yard with a babbling brook and small waterfall. I came for a writing retreat and found everything I needed during my stay--especially abundant coffee, which I was particularly grateful for :)

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