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

Beautiful Country Farmhouse w/ Pool
This is a beautiful, cozy and tasteful home. We loved the contrast between the original 300 year old farm beautifully maintained and renovated and the newer rooms. Kitchen was great and the fireplace worked wonderfully. Wifi and office space were perfect to get a few hours of work done. Had a great week skiing in nearby Mohawk and visiting Litchfield and Bantam. It was useful to inquire about the lay out and steep stairs. Daire was super responsive and helpful throughout our stay. We had a wonderful time. Thanks for sharing your home!

Private Hudson Valley Country Retreat
My friends and I stayed in Stormville for a girls trip. The house is even better than the photos. The property and landscaping are stunning, we loved just staring out at the view with a cup of tea. The kitchen was impressively stocked with lovely teas and all the cooking gear we needed. Check in and communication were effortless. The location while a bit far from groceries (15m drive) was no more than 15-30m from lots of activities, small towns and hiking trails. We also loved how accessible it was from Metro North as we were coming from the city for just a short trip. It was very easy to get to and we all couldn't stop talking about how we hoped to return. Highly recommend!

Pool House
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

Garden Level Suite with Beautiful Pool
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!

4Br Mountain Brook House on 130 acres w/ trails
Rick's House (Hemlock House) was a wonderful getaway! We unfortunately didnt hit the best weather but the house was perfect for a cool and rainy long weekend both indoors and out. The open first floor with huge kitchen was great for hanging out and cooking with alot of cozy nooks to read and relax. There was a lot of various outdoor spaces and decks to lounge on as well and the hot tub was perfect for the cooler cloudy weather. The bedrooms were all comfy and each room having its own bathroom was another plus. We all loved the sounds of the creek and being able to walk around the trails in the back. The House is in a fantastic location - only 10 minutes from Rhinebeck which has everything you need and is great for walking around, shopping and dining. Rick was informative and provided a great guidebook with clear instructions and local resources and recommendations. Thanks for a lovely stay!

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
My family and I had such a wonderful time. The home and the surroundings were so beautiful, peaceful, quiet, and relaxing. Everything was very clean, and the bed and pillows were so comfortable. My toddler especially enjoyed the cute bathtub in the master bedroom. The pool was beautiful, just wished we were there when the weather was nicer, as the water was quite cold. The restaurants nearby (10 mins away) were so good, we especially loved everything from a place called Kingsley Tavern. Overall, loved our stay and would definitely stay here again!

Moody Pond House: Weekend Country Escape
We stayed 4 nights at the Moody House. Description of the house was perfect- check-in was seamless. We loved all the natural lighting in the house. Even with a lot of rain, we enjoyed the views of the backyard and quiet area. We didn’t use the hot tub but was provided a video on how to use. Jessica and Adrian provided a great list of shops, grocery stores and restaurants- which we used, so much appreciated! Highly recommend this Airbnb.
Weekly house rentals

Quiet and Cozy Getaway
We came in for a bridal shower. I 100% recommended to other out of towners this listing. Wanted to stay a few more days but our schedules wouldnt allow. It is definitely worth the 5 star review!! Will be staying here in the future to visit my sister less then 2 miles away!!

Gunn Brook Mountain House
This charming, rural home has a touch of mid-century fun throughout. But the best part is the gorgeous lawn and waking up to the sound of the rushing brook right outside the window. Rebecca was so friendly and responsive and included lots of little touches that were very thoughtful.

Private Woodland Sanctuary—3 mins to a lake beach!
this place is magical. my sisters and I have stayed here twice now, for her wedding and now for mine. both times the home has been clean and the overall experience has been wonderful.

Nature lover’s retreat in NWCT, breathtaking views
Kellen and Samantha's home and property are very special--a wonderful location for a restful retreat in nature that is also a short drive to several charming towns in northwest Connecticut. The hilltop site offers breathtaking views of surrounding mountains, valleys, and forest. The residence sits atop a long driveway off a gravel road so is serenely quiet and private. Inside, the space was immaculate, thoughtfully designed, and very comfortably furnished. The shower, bed, towels, and linens were all particularly fantastic, as was the full kitchen which allowed us to cook nightly. The area is exceptional for hiking, culinary delights, and all sorts of shops. And our hosts were proactive, helpful, and clear in all of their communications. We really loved staying here, as did our dog, and we hope to return. Highly recommended!

UB’s Corner
Our stay at Ellen’s Lake House was perfect. It was comfortable, clean and the view of the lake is amazing. My husband enjoyed fishing and we both loved being on the water. Ellen was helpful and made our stay a wonderful experience.

Harwinton Cottage
The house is absolutely gorgeous and is in a quiet neighborhood. But it's also not too far from shops and things to do. Our host was very responsive and accommodating and I would recommend booking this house any time.

Carriage House on Smith Pond!
The accommodations are beautiful as well as the grounds and the view from the kitchen and living area. Everything was spotless and the Airbnb is equipped with everything you need for a lovely relaxing stay. Todd and his wife are wonderful hosts and there when you need them. As a welcoming gift they provided a lovely fruit tray, muffins and farm fresh eggs! This Airbnb is truly a gem!

Historic Charm
This is a historical house, updated for modern expectations. Kitchen is beautiful, baths are redone and clean. Historical touches are preserved - beautiful staircase and wood floors from the 1800s. The house matches the description, and is comfortable. Susan, the host has her communication levels just right- will make sure you have everything you need, and will respond quickly. Thank you so much!
Private house rentals

Bantam Beauty: Surrounded By Nature!
Friendly hosts who put a lot of effort and thought into their home. Communicated well and their home was exactly as described - in nature and high-end amenities for a family. Would recommend to anyone.

Don’t miss out on this cozy New England escape!
Would gladly stay here again. Shawn was responsive and the place had everything we needed. Hope to come back to this part of CT again

The Inn at Knife Shop Falls- Historic Waterfront
Our getaway for the weekend was perfect! We enjoyed the home, pond and a nearby preserve for a hike. Thank you for the stay!

Beautiful sun filled cottage in the woods
We hosted a Friendsgiving here and it was so lovely. From the falling snow to the open concept, it was a wonderful gathering abode for the holiday. Thank you!

Artist's Retreat In The Woods | Five-Acre Backyard
Our son attends a nearby boarding school, and during our visits, we have stayed at hotels and other Airbnbs. This home was one of our favorites. My husband commented that “this was easily my favorite place we’ve stayed.” We enjoyed the kitchen/living room layout to cook and hangout, and the bed was very comfortable. There are two hiking trails, both less than 10 minutes away, that we enjoyed while here, too. I definitely recommend a stay here.

The Art House: 5-Acre Getaway w/ AC & Firepit
My family and I stayed at this Airbnb during my wedding weekend and it was perfect! The house is beautiful. It had one bedroom and bath downstairs for my grandma to stay in so she didn’t need to go up the stairs. The kitchen is amazing! It was a great distance to the Candlewood Inn where we got married. Jessica was very responsive and always checking in. Would definitely stay here again!

Magical Woodland Getaway
Lovely home, beautifully decorated, in great country setting with easy access to neighboring towns. Our host was very responsive.

Lake View Cottage
Enjoyed staying 4 nights. The house is beautifully designed and decorated with lots of natural light. Great location across the street from the Lake and walking distance to New Preston shops, coffee and restaurants. Enjoyed daily morning walks around the Lake. David was a great host- responds within minutes, easy check-in and check out. Highly recommend.
Quick stats about house rentals in Litchfield
Total rentals
80 properties
Nightly prices starting at
₹7,754 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
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- Fairfield Beach
- Yale University
- Six Flags New England
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Woodmont Beach
- Seaside Beach
- Bushnell Park
- Calf Pasture Beach
- Jennings Beach
- Silver Sands Beach
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Walkway Over the Hudson State Historic Park
- Clinton Town Beach
- Sherwood Island State Park
- Bayview Beach
- Grove Beach
- Hudson Highlands State Park
- Kent Falls State Park
- Wildemere Beach
- South Pine Creek Beach