House vacation rentals in Litchfield County

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Popular amenities for Litchfield County house rentals

House rentals with a pool

Guest favorite
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 Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars7 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 stars5 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 favorite
Home in New Milford
4.95 out of 5 average rating, 21 reviews

Spacious and relaxing New Milford 5br home w pool!

ElizabethRating, 5 stars4 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 favorite
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 Washington
5 out of 5 average rating, 6 reviews

Zoom In Lux 5*Washington "Calhoun 4BR" PoshPadsCT

AllisonRating, 5 stars9 months ago
Stephen was very accommodating as we had a reservation canceled last minute. Accommodations were beautiful. Scenic views. Infinity pool was amazing. Very comfortable. Washington is a great town with nice restaurants and shops. We would definitely stay at one of Stephen’s properties again.
Top guest favorite
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 favorite
Home in Warren
5 out of 5 average rating, 47 reviews

Moody Pond House: Weekend Country Escape

ShivaniRating, 5 stars1 month ago
Jessica and her husband were truly such lovely hosts, and have a beautiful home. Ahead of our stay, they sent us a great package of local restaurants and things to do, going above and beyond to even offer to connect us to local hospitality in the area. We had a few questions about how to use Uber in the area and Jessica & Adrian were very responsive. The house itself is exactly as pictured-- very stylish, relaxing, clean, great light, modern appliances and everything you'd need as a guest. Very easy to access the home, which can be a hurdle with other vacation homes. We visited as a group of 4 and really felt the home was perfect for a couples getaway weekend. I'd definitely recommend this home to others looking for an idyllic, inspiring weekend away and really appreciate the kindness of this family as hosts!

Weekly house rentals

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

Tiny Home Away From Home - Complete Privacy, Peace

MarceloRating, 5 stars1 week 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 !
Guest favorite
Home in Sharon
4.93 out of 5 average rating, 182 reviews

Charming CT Country Farmhouse for group getaway

Jon & StefRating, 5 stars1 week ago
This Sharon home is the perfect spot for people who love old quirky homes. Hidden doors, lots of beadboard, beautiful windows original to the house, creaky floors, floral wallpaper, etc. We are those people! For any parents with toddlers: the house is close to the road on a hill so we had to keep an eye on our 3yo outside but we didn’t mind. We played a lot of games in the living room overlooking the trees and made s’mores at night outside. My girls loved the swing in the screened-in porch. Lots of hikes nearby. Good restaurants within 20 minutes. Lots of little downtowns to explore. Our friends live in Amenia so it was perfect to only be 15 min away. Would stay here again!
Guest favorite
Home in Colebrook
4.96 out of 5 average rating, 74 reviews

Log Cabin sleeps 30 bunk style on 350 acres

RomaricRating, 5 stars7 months ago
Beautiful time, we can't wait to come again.
Guest favorite
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 Watertown
4.78 out of 5 average rating, 37 reviews

Cozy Cottage

MayaRating, 5 stars1 week ago
We had a lovely stay here! Hector was incredibly helpful and responsive and very friendly. Big thanks to Hector for making our weekend so smooth and enjoyable.
Superhost
Home in Bristol
4.79 out of 5 average rating, 52 reviews

Modern Homey Heaven | Garden view, Patio, Games

JenniferRating, 5 stars1 week ago
This place was exactly as described. Very spacious!
Guest favorite
Home in Sharon
4.92 out of 5 average rating, 150 reviews

Cottage In Nature w/Private 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!
Top guest favorite
Home in Middlebury
5 out of 5 average rating, 10 reviews

New England Charm!

DavidRating, 5 stars3 months ago
The house had everything I needed for a business-related stay near Waterbury.

Private house rentals

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

Cozy Family and Pet friendly 3 br Home

JennaRating, 5 stars4 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 favorite
Home in Roxbury
4.95 out of 5 average rating, 41 reviews

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

KatieRating, 5 stars4 days ago
Konstantino is a top notch host. He was lightening fast in his responses to my questions. Very polite, respectful, efficient, generous, personable, and friendly. The house was beautiful. I wish my kitchen looked like this one. The beds were so comfortable, as were the couch and chair. I wish I had that black chair! It made me never want to get up! The artwork was beautiful. The house was so easy to find, even in the pitch black! The sensor lights were so helpful. The drive was so beautiful. The houses were gorgeous. New Milford was quaint and beautiful. The River and Rail Cafe there was delicious. We also visited a mine. The museum in that town looked like it was probably worth a visit. We didn’t have time to explore it. The shower head was very nice. The shampoo, conditioner and soap had the best scent! Netflix worked great. I highly recommend this place for a getaway. You can’t go wrong with this host! Enjoy!
Top guest favorite
Home in New Fairfield
5 out of 5 average rating, 27 reviews

Direct Lake Access - Priv Dock, Kayaks, EV Charger

PriscilaRating, 5 stars5 days 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!
Guest favorite
Home in Bridgewater
5 out of 5 average rating, 29 reviews

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

AlexandraRating, 5 stars4 days 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, 91 reviews

Charming Home in Litchfield County on a MAIN ROAD!

JoannaRating, 5 stars3 weeks ago
Cute, cozy home! It is an old home, but with such character and beautifully decorated. I can't say how awesome it was to wake up and have a coffee truck right there, with the most amazing coffee ever! You must try the raspberry caramel macchiato- it's pink! The big bed was very comfy, the house felt spacious for a tiny place. I loved the home manual that was available to orient me to the area and things about the home. I would definitely stay here again!
Guest favorite
Home in Winchester
4.88 out of 5 average rating, 26 reviews

Winchester House with wifi/high speed internet.

NedzadRating, 5 stars4 months ago
I would definitely go back to Krissie’s place again, highly recommended!
Top guest favorite
Home in Kent
4.96 out of 5 average rating, 25 reviews

Country retreat on 4 private acres

SamanthaRating, 5 stars1 month ago
We had a great trip at Monica and Hugo’s house!
Guest favorite
Home in Southington
4.95 out of 5 average rating, 111 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

ThulasiRating, 5 stars2 weeks ago
We had a fun family get together in this nice cabin! It is a perfect vacation spot during summer, unfortunately we were there on a rainy weekend!

Destinations to explore