Cottage holiday rentals in Litchfield County

The Artist Cottage was a great secluded retreat. We loved how charming and cute the place looked. The colorful decor and charming antiques in the cottage made it feel special. The amenities were well taken-care of and we especially loved the hot tub, the outdoor fireplace, the spacious lodge, and the large, modern soaking tub. We enjoyed hanging out in backyard, where we could listen to numerous birds while sitting by a little waterfall in the morning. We appreciated the well-stocked kitchen. It was just a short walk from some nice hiking trails and we loved that it was only a short drive to town. Overall, we highly recommend this stay!

My friend and I stayed here for a quick two-night getaway and had a great experience. The space is quiet, cozy, and super well taken care of. The view of the water from the living area is beautiful, and we spent both mornings sitting outside with coffee, and afternoons enjoying the view from the hot tub. We appreciated that the kitchen was fully stocked with all the cooking equipment we needed for nights in—and that Mary had a whole list of spots to check out for adventures out (local shops, antique spots, and really solid lobster rolls!) If you’re looking for a low-key, clean, calm place to relax, recharge, and still have easy access to town, this is a great pick. We’d absolutely come back.

Such a lovely home! actually better than I expected! Will definitely book again. It’s honestly a no brainer after staying there. I can recommend this place 100%!

Thank you Ellen for the easeful stay at your cottage with clear instructions. The surroundings are beautiful. We saw an eagle at the lake!

Martin was a very responsive host! The property was great overall.

My girlfriend and I had a great time staying at Joktan’s place. We really enjoyed the home as well as the amenities that came with it. Joktan, provided excellent communication. Would recommend staying here!

The Cottage at Blackberry River Inn was beautiful and exactly what we needed for the weekend. Breakfast was included and wonderful. This place is a gem and we will be back for sure.

Ellen's cottage was the perfect place for me to unwind and enjoy a peaceful vacation. The surrounding area was serene and the lake was such a bonus! The cottage had everything I needed and more and the bed was so comfortable which isn't always the case with airbnbs so I was thrilled. Ellen was always very sweet and responsive and all around a great host. 10/10 recommend this spot to anyone! Thanks for a great stay!

This place was wonderful. We were only there for a quick stay, and it was rainy, but that was ok because the cabin was so cute and cozy and fun. A bit of time sitting in the chairs out front in the morning with my coffee was exactly the quick weekend rejuvenation I needed. The cabin had everything we needed (and plenty of things we didn't need on this trip, but you might! I could see us playing board games or relaxing out on the back patio on a future trip.) A previous reviewer said this spot is what you expect an Airbnb to be, and that's exactly right. We picked it at first because it was convenient to a few Westchester things we needed to do, but we didn't want to drive home afterwards to CT on a summer Friday night. Spending this little bit of time in the Carmel area was genius because now we can't wait to go back there specifically for a real visit!

Laurence and Ilze were incredible hosts, incredibly helpful and responsive, going above and beyond to sort out our needs. The house was as advertised and we had a a great time at their place. Should we be back in the area we’d definitely try to stay with them again!

This was a lovely cottage and location, part of a private beach community, on a very quiet road, with partial views of the Long Island Sound. Gail was thoughtful to put out a nice welcome basket and some cold sodas and bottle water in the fridge. Perfect spot for two to three people. Close to Guilford main green, dock and nearby Stony Creek and Madison. We didn't make use of the bikes and kayaks bc it rained in the mornings, but we enjoyed one of the two beach just a few minute walk away. Jacob's cove area is a gem.

A very cute and wonderful place to stay! Cozy, clean, private, and incredibly close to the beach! Lisa was extraordinarily understanding about the check-out time and process, would LOVE to stay again! :)

Excellent location for local shopping, lots of food choices, delicious breweries. Most importantly VERY close by for climbing & getting out to nature. The Woodstock & Kaaterskill wilderness areas are within 30 minute drive. Lots of stunning views for a decently low mileage. Rip Van Winkle bridge is 9 minutes away if you want to explore the other side of the Hudson. The place has all the amenities you’d need for a getaway. Very clean, host was very responsive; even on the Memorial Day holiday. Will be back!

Had a beautiful stay and would 100% return and tell friends about it. Cute and cozy stay, lovely little town and beautiful views.

Cute little pad to explore the Hudson Valley from! Would recommend to anyone looking for an easy-going place to stay in Pine Plains.

We had a wonderful stay at this charming, comfortable, and clean cabin, with a nice yard for our dog. We especially loved sitting in the backyard listening to the birds…so peaceful! The location was perfect, close to a nearby town and some great antique stores. Would definitely recommend!

else's place is gorgeous, the pictures are a perfect reflection of the property. the qood burning stove is gorgeous and it was amazing to spend the evenings chatting about our days adventures watching the logs burning. the gardens are beautiful, the beds are really comfy and big and the kitchen well stocked. I would deffi lately recommend this lovely home from home.

Lovely cottage and a perfect location if you’ll be at Omega Institute which is 4 minutes away. Close to Rhinebeck Village too. Beautiful grounds and well appointed home. Extremely clean and well planned space. Comfortable bed, soft linens. Spacious kitchen made meal prep easy and when I asked about a blender the host was very responsive and a new blender was waiting for me on the porch. Really restful place with a private and calming back porch. Very serene property. I cooked dinner instead of going out on Saturday night because the space is so welcoming and relaxing, especially after a long day of classes at Omega. Comfortable sofa, wool throw, and Netflix. A perfect evening. Would love to stay again the next time I’m in the area.

Charming home, and Cath was especially helpful with late night dining accommodations.

A truly lovely spot! Quiet, relaxing and comfortable. We enjoyed the view of the water, reading on the patio in the lounge chairs and sitting on the bench overlooking the beach. We would love to come back again.

The location was very quiet and an easy walk into Tivoli. I recommend that the refrigerator is raised by putting a cabinet underneath, or a taller refrigerator. I microwave would be a definite plus.

Ina’s home, on 48 acres, is consistently highly rated, as it should be. It’s a perfect retreat for 2-3 people, secluded, but only a short drive to Litchfield. Ina kindly met us to give a 10 min tour of the property. Although not huge, the house is a congenial, inviting space, which was beautifully designed/built in the 50’s and sympathetically incorporates architectural components from a much earlier period. The setting, with several areas to sit out in, affords peace and spectacular sunsets. All said, this is a unique, magical space.

My wife and I stayed at Elena's place over the memorial day weekend. The weather was not that co-operative, but still the views were beautiful, the place peaceful, and in a great location to get all around Connecticut.

Our extended family goes tent-camping in nearby Taconic State Park. We enjoy the campsite during the day but repair to this sweet, charming house nearby to sleep. It’s clean and comfy and within one minute of the campsite. This house let us enjoy the best of both worlds. Thank you for a lovely weekend.