House holiday 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!!
Guest favourite
Home in Stormville
4.94 out of 5 average rating, 178 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars5 months ago
Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back
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.

Weekly house rentals

Guest favourite
Home in Copake
4.9 out of 5 average rating, 134 reviews

Modern, cozy log cabin in Copake

JayRating, 5 stars2 months ago
Our stay at Julia's home was perfect! We all felt right at home, our grand daughter had lots of books, which she loves and other kids toys. The log cabin was more beautiful than pictured and the claw foot tub in the upstairs suite was the icing on the cake.
Guest favourite
Home in New Milford
4.99 out of 5 average rating, 84 reviews

Waterfront Family Retreat on Candlewood Lake

AshleyRating, 5 stars1 month ago
Had a great stay with my family. Home was even better than the pictures, very clean with all the amenities! Great yard to entertain and play with the kids when the weather was nice!
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 Brookfield
4.82 out of 5 average rating, 22 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..
Guest favourite
Home in Tolland
4.95 out of 5 average rating, 57 reviews

Spacious Home w/ Hot Tub in Private Lake Community

AuraRating, 5 stars3 weeks ago
The place was incredibly beautiful. The photos did not do it justice. It is in the middle of nowhere. Tina was very detailed in her instruction and one of them was that you must bring groceries because the closest grocery store is 30 minutes away. If you decide to book this place, read her detailed instructions. They are very helpful. The home offered a full kitchen which made it so easy for us to prepared our family's meals without struggling. The hot tub was such a treat. The basement had lots of games, a couch to launch and another TV. Perfect if you come with children. We were seven adults and we did not feel that we where on top of each other. The high ceiling truly made one of our boys (the giant) feel at home. Even the basement had a high ceiling. Pretty cool. Tina was incredibly nice and flexible. Check in is at 4 pm and we arrived earlier. We decided to contact her to see if it would be okay to check in earlier and she accommodated us. Thank you soooo much.
Guest favourite
Home in Enfield
4.91 out of 5 average rating, 11 reviews

3 bdrm house great neighborhood

J DavidRating, 5 stars11 months ago
Wonderful place for our family to spend the weekend while we attended our daughter's graduation a half hour away in MA. Clean, comfortable, spacious and charming in a quiet neighborhood. Auria provided clear instructions, check in was a breeze, and she was extremely proactive and helpful. She responded immediately to questions and was always cheerful and polite. One of the best Airbnb experiences we have had so far. I can not recommend this highly enough.
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 stars4 days 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!
Superhost
Home in Rhinebeck
4.82 out of 5 average rating, 268 reviews

Private Lakefront Bungalow

JosephRating, 5 stars1 month ago
We loved the place! My fiancé, Gloria and I wanted a little get away for the weekend for her birthday. This place was perfect. 1-2hours drive from the city. The lake was amazing and it was very private. We had a great time. We did canoeing too. It was fun! We hope to be back again in the future. Thank you, Robin!

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 Hartford
4.9 out of 5 average rating, 73 reviews

Renovated & Modern Victorian in Historic West End

JoshuaRating, 5 stars1 month ago
I’ve stayed here a few times. I keep coming back because Antonio is a great host. His house is always convenient, clean and comfortable. Can’t really ask for more!
Guest favourite
Home in Dover Plains
4.9 out of 5 average rating, 31 reviews

Hillside Grove

StefanieRating, 5 stars1 month ago
Jennifer’s place was amazing! The house is super clean, very neat and organized, and comfortable furniture. It is exactly as described and Jennifer is very responsive. Definitely worth a repeat trip!
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 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 Otis
4.93 out of 5 average rating, 15 reviews

Spacious Lake Front Home

JeanRating, 5 stars5 months ago
Beautiful location in Otis, right on the lake and so peaceful. The house is very spacious and easily accommodated our family ( 7 adults and 2 children). All the windows in the house provided great views of the lake, especially from the deck. Our host Nick was very responsive when we had questions or any concerns. Would be nice to come for a stay during the summer.
Guest favourite
Home in North Salem
4.94 out of 5 average rating, 32 reviews

North Salem Home with Pool & Great Yard

MauricioRating, 5 stars6 days ago
Exactly what my family needed for a quiet getaway from the city. The huge yard and quiet surroundings were a blessing. Made friends with the woodpecker while enjoying a cup of coffee on the patio :) The house is well equipped and kept immaculate. the weather helped in allowing us to both enjoy the warmth of the fireplace, while also enjoying the hammocks. We loved our stay so much that we extended our stay by three days. Susan is a great host and is very thoughtful and friendly. I highly recommend this home to anyone ! Looking forward to coming back.,
Superhost
Home in Springfield
5 out of 5 average rating, 8 reviews

VDM Property!

AlinaRating, 5 stars4 months ago
We enjoyed our stay at this property. It was extremely clean! There were basic necessities provided. It also had a cute, fashionable interior design. The shower and bedrooms were nice. We liked the layout of this property. Our only issue was that either the heater in the master bedroom wasn't working, or we couldn't figure out how to use it.

Quick stats about house rentals in Litchfield

  • Total rentals

    80 properties

  • Nightly prices starting at

    $138 AUD 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