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House holiday rentals in Litchfield County

Find and book unique houses on Airbnb

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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 stars6 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 Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars6 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Superhost
Home in Millerton
4.88 out of 5 average rating, 24 reviews

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

JakeRating, 5 stars4 months ago
Property was good could be a bit cheaper for the value of it . Host is very good at communicating and house was clean . It did the job
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 stars3 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 stars1 month 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, 16 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

SidRating, 5 stars1 month 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, 23 reviews

Country retreat on 4 private acres

CamiRating, 5 stars3 weeks ago
We had a great stay at Monica’s place in Kent! The house was extremely cozy, clean, and comfortable. Monica was incredibly responsive, making our stay even better. We would definitely come back!
Top guest favourite
Home in Warren
5 out of 5 average rating, 45 reviews

Moody Pond House: Mohawk Ski Mountain Getaway

ScottyRating, 5 stars1 week ago
We had a fantastic stay at this home! It had everything we needed for a comfortable and relaxing getaway. The fireplace was a perfect touch—we had a fire going every day, which made the space feel extra cozy. We also loved unwinding in the hot tub, especially after a day of exploring. Another favorite was listening to records on the record player—it added such a fun and nostalgic vibe to our evenings. The wildlife around the property was incredible; we saw so many animals, including a beaver that built an impressive dam right in the backyard! It was such a unique and peaceful experience. We’d absolutely stay here again!

Weekly house rentals

Guest favourite
Home in Watertown
4.9 out of 5 average rating, 52 reviews

Tiny Home Away From Home - Complete Privacy, Peace

HeatherRating, 5 stars1 week ago
Great little house in a quiet, safe neighborhood
Superhost
Home in Salisbury
4.95 out of 5 average rating, 98 reviews

The Barn - Rustic Chic Loft, Hotchkiss, Lakes, Ski

JoseRating, 5 stars3 weeks ago
Awesome place and great host!! Highly recommend
Guest favourite
Home in Sharon
4.94 out of 5 average rating, 177 reviews

Charming CT Country Farmhouse for group getaway

KevinRating, 5 stars1 week ago
A truly exceptional home with lots to offer. Very out of the way, great for relaxing. Tons of space, with two living rooms, a large dining room, a large screened in porch, a deck, and two kitchens, one of which is fully stocked! The bedrooms were nice, and the decor was very unique and fun to find. Overall, could not have asked for a better place for a weekend getaway with friends.
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 stars6 months ago
Beautiful time, we can't wait to come again.
Guest favourite
Home in Brookfield
4.82 out of 5 average rating, 22 reviews

Lake Candlewood Retreat

FabioRating, 5 stars4 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 Bristol
4.78 out of 5 average rating, 49 reviews

Modern Homey Heaven | Garden view, Patio, Games

JimmyRating, 5 stars3 months ago
The host is a wonderful lady, I missed a watch worth more than 20,000 dollars in the room when I check out at 10am, she went back to the room at 1pm and returned it to me warmly, the inside of the room is also clean and tidy, the surrounding is very quiet, I will choose this place again next time I have the opportunity👍, thank you Farah!
Guest favourite
Home in Sharon
4.92 out of 5 average rating, 150 reviews

Last minute special! Cottage In Nature w/River

FaithRating, 5 stars1 month 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!
Top guest favourite
Home in Middlebury
5 out of 5 average rating, 10 reviews

New England Charm!

DavidRating, 5 stars2 months ago
The house had everything I needed for a business-related stay near Waterbury.

Private house rentals

Guest favourite
Home in New Fairfield
5 out of 5 average rating, 25 reviews

Direct Lake Access - Priv Dock, Kayaks, EV Charger

JooyeonRating, 5 stars1 month ago
We had a such great time in a great house. Spectacular views and plenty of places for 6 people. Also very cozy and clean house. Would definitely come back for summer and recommend to other friends! Thanks for letting us stay at your place!
Guest favourite
Home in Bridgewater
5 out of 5 average rating, 26 reviews

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

BrettRating, 5 stars4 days ago
The Art House was the perfect spot for us to gather as a family. I said if I was to have an Air B&B it would look like this. The interior Fireplace and the outdoor firepit was a nice place to gather. Plenty of parking. As I walked around the property before I left (March) was thinking how nice the place would look in the Spring when the manicured yard and shrubs fill in. Highly recommend this property for anyone in the area looking for a comfortable place to stay! Thank you! Brett
Guest favourite
Home in Goshen
5 out of 5 average rating, 11 reviews

Peaceful Countryside All-season Retreat

CordellRating, 5 stars8 months ago
It is even better than described! It was a perfect place for our different family members to hang out. Easily accommodates 8 people for meals, games, both indoors and outdoors. Everyone had enough space to gather, and to have time and space to themselves. The playground is fun, they have cornhole and other outside fun! The gazebo has screens so you can be outside and away from the bugs. And it has a table if you want to play games or do puzzles out there too. The property is very private, and the host is very responsive!! Highly recommend this stay.
Superhost
Home in Torrington
4.89 out of 5 average rating, 87 reviews

Charming Home in Litchfield County on a MAIN ROAD!

TylerRating, 5 stars2 months ago
Great place to stay while visiting for a Mohawk Mountain trip. 25 minutes to the ski area. The Batchy Brew coffee truck was also very convenient and has amazing coffee.
Superhost
Home in Waterbury
4.78 out of 5 average rating, 9 reviews

Vintage Bungalow in Waterbury

JoshuaRating, 5 stars2 months ago
Sharlene’s home was perfect for my Yale acapella group! We had 10 people staying for a weekend and we loved the cozy space. Sharlene was extremely responsive throughout the weekend, getting us everything we needed like shampoo and a space heater for the third floor. The home was definitely on the more older, rustic side but I didn’t mind it at all.
Guest favourite
Home in Winchester
4.88 out of 5 average rating, 26 reviews

Winchester House with wifi/high speed internet.

NedzadRating, 5 stars3 months ago
I would definitely go back to Krissie’s place again, highly recommended!
Superhost
Home in Watertown
4.91 out of 5 average rating, 22 reviews

Historic Litchfield County Home

HollieRating, 5 stars6 months ago
The unique home was a truly amazing experience. The grandchildren loved the yard. The porch was a peaceful gathering place or a serene place to just think or write or just sit and enjoy. A short drive brings many things to do or see. The piano was amazing. The artwork and history contained in those walls was a bonus gift.
Guest favourite
Home in Southington
4.94 out of 5 average rating, 109 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

Johan SebastianRating, 5 stars1 week ago
We had an amazing stay at this Airbnb! The place was spotless, and the host was incredibly attentive and easy to communicate with. The location is perfect, with stunning views of the lake. Watching the sunrise and sunset from the many windows was absolutely breathtaking! The home is well-maintained, clean, and has everything you need for a comfortable stay. We truly enjoyed every moment and will definitely be coming back. Highly recommend this place!

Destinations to explore