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

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!!

The Getaway-HOST & Co.
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.

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

Spacious and relaxing New Milford 5br home w pool!
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.

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.

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.

Country retreat on 4 private acres
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!

Moody Pond House: Mohawk Ski Mountain Getaway
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

Tiny Home Away From Home - Complete Privacy, Peace
Great little house in a quiet, safe neighborhood

The Barn - Rustic Chic Loft, Hotchkiss, Lakes, Ski
Awesome place and great host!! Highly recommend

Charming CT Country Farmhouse for group getaway
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.

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

Lake Candlewood Retreat
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..

Modern Homey Heaven | Garden view, Patio, Games
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!

Last minute special! Cottage In Nature w/River
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!

New England Charm!
The house had everything I needed for a business-related stay near Waterbury.
Private house rentals

Direct Lake Access - Priv Dock, Kayaks, EV Charger
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!

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

Peaceful Countryside All-season Retreat
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.

Charming Home in Litchfield County on a MAIN ROAD!
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.

Vintage Bungalow in Waterbury
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.

Winchester House with wifi/high speed internet.
I would definitely go back to Krissie’s place again, highly recommended!

Historic Litchfield County Home
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.

Connecticut Chalet - Private Pond, Firepit, Views!
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
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- Yale University
- Catamount Mountain Ski Resort
- Thunder Ridge Ski Area
- Taconic State Park
- Woodmont Beach
- Bousquet Mountain Ski Area
- Six Flags New England
- Marvin Beach
- South Pine Creek Beach
- Thaddeus Hait Farm
- Kent Falls State Park
- Wee Burn Country Club Inc
- The Stanwich Club
- Woodway Country Club
- Harbor View Beach
- Long Beach
- Calf Pasture Beach
- Saint John Beach
- Old Mill Beach
- Sherwood Beach
- Sherwood Island State Park
- Burial Hill Beach
- Alvord Beach
- Southport Beach