Holiday houses in New Fairfield

4.98 out of 5 average rating, 148 reviews

Home in Brookfield

Stay at Old Dorset Farm & create lifelong memories

This 1905 Historic Old Bakery is the perfect location to create lifelong memories while exploring quaint New England. Set on 4 acres, with a lake, trails and golden rolling hills just minutes away, you’ll enjoy all of New England's beauty. Hiking, kayaking, antiques shopping or gallery visiting... it can all be done right here. But you don't have to go anywhere. The two fireplaces invite you to just stay, relax and enjoy the complimentary bottle of Prosecco. Follow us on Insta: @Old_Dorset_Farm

5 out of 5 average rating, 33 reviews

Direct Lake Access - Priv Dock, Kayaks, EV Charger

Welcome to "Anchors Away", nestled directly on a main artery of Candlewood Lake, CT. 90 min from NYC. Feet from lake edge. Kayaks & EV charger. W/car arrival, stand on your perch, observe the views & cascade down the STAIRS to the private grounds. Drop your bags, grab a towel & cartwheel into the lake. W/ boat arrival, drop your anchor at our private dock. Enjoy 3 BDR 3 full BTH home, with lake access year-round. Walkable community. Sleeps up to 8 maximum. No gatherings. No daytime visitors.

4.94 out of 5 average rating, 144 reviews

Guesthouse in Brewster

Sherwood Barn - close to ski mountain

Our guests stay on the SECOND floor of the barn in a 1200 Sq Ft, fully reno'd apt that sleeps 6. Located about 1 hour from NYC you will find peace and serenity in the middle of nature on this 4 acre estate (that also contains our main home) where you can get away from it all. unwind this way or visit local attractions like Thunder Ridge Ski Mountain, snowshoe/ X Country skiing, hike/bike/running trails, restaurants and local cafe's. Great oasis to kick back and spend time with family.

4.97 out of 5 average rating, 75 reviews

Hilltop Retreat- Lakefront with Dock

Enjoy all that Candlewood Lake and Squantz Pond State Park have to offer in the comfort of our home. Come reconnect with love ones and relax in the serene surroundings. This waterfront property has a private dock, features 2 bedrooms, 2 full baths, and views from almost every room in the home, plenty of indoor and outdoor entertaining space and a wood burning fireplaces to keep toasty during chilly evenings. Toiletries, all linens are provided. Please read house rules before booking.

4.95 out of 5 average rating, 203 reviews

Cottage in New Milford

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Superhost

Cabin in New Fairfield

4.84 out of 5 average rating, 76 reviews

Candlewood Cabin - with Private Waterfront

Candlewood Cabin is a cozy retreat located right on the water. Enjoy stunning views of Squantz Pond from the private deck, or take a quick walk down to the waterside lot for some fishing, swimming, or boating. Inside, the cabin has a modern kitchen with all the necessary amenities. The living room features a gorgeous view of Squantz Pond. With natural beauty all around, this cabin is ideal for couples or families looking to get away from it all and enjoy a serene lakeside holiday.

4.92 out of 5 average rating, 118 reviews

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

4.97 out of 5 average rating, 390 reviews

Cabin in Sherman

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

4.92 out of 5 average rating, 281 reviews

Apartment in Brookfield

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

4.99 out of 5 average rating, 313 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

4.98 out of 5 average rating, 124 reviews

Cottage in Pawling

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

4.96 out of 5 average rating, 331 reviews

Cabin in New Fairfield

The Little Lake Cabin— hot tub, fire pit, & kayaks

Named one of the best Airbnbs in CT by Business Insider, The Little Lake Cabin is the perfect place to soak in the magic of nature by relaxing, hiking, and enjoying the lake. The cabin is a place to slow down and reconnect. Spend your days on the lake, exploring nearby towns, wineries & antique shops & your nights in the hot tub, by the fire pit roasting s'mores and gazing up at the stars.

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Other great holiday rentals in New Fairfield

4.79 out of 5 average rating, 24 reviews

Candlewood Knolls Cabin

MelanieRating, 5 stars1 month ago

We enjoyed our stay, the complementary offer was wonderful. The place was very clean. Comfortable beds. The community had a lot to offer.

5 out of 5 average rating, 39 reviews

Candlewood Isle Cabin ~ Dog Friendly~ Lake ~ Dock

AlesiaRating, 5 stars1 month ago

The location suited our needs perfectly. It was close to our Jehovah’s Witness facility in Patterson NY. We had a morning tour which made it very convenient, only 20 minutes away. We not only enjoyed the peaceful quietness, we were also able to do a little fishing at the boat docks right on the property of Candlewood Isle and caught a few fish.☺️

4.67 out of 5 average rating, 24 reviews

Fun at the lake

DavidRating, 5 stars9 months ago

Beautiful place great host. Everybody had a great time.

Home in Danbury

4.86 out of 5 average rating, 126 reviews

Private apartment

SunRating, 5 stars1 week ago

My stay was very comfortable and peaceful! The location was very quiet and accessible to plenty of restaurants via delivery, as well as only a ~10 min drive to downtown if desired. I was given a tour of the space when moving in since I bumped into one of the hosts, which made the move in smooth and easy to understand.

Home in Pawling

5 out of 5 average rating, 5 reviews

Quaker Hill Cottage

BethRating, 5 starstoday

Ahhhh- what a gorgeous and peaceful retreat that Emilie and Brandon have created. Our family of 4 (2 kids that had a ball here) couldn’t stop gushing about how cozy and very cool the cabin is. The photos do not do the interior of this home justice- it is absolutely gorgeous, yet so comfortable. The setting is stunning! If quiet walks and a gourmet kitchen are on your must have list for a get away, this is your spot!!

4.62 out of 5 average rating, 21 reviews

King Bed, Grill, Pool Table, Air Hockey, Ping Pong

WendyRating, 5 stars1 week ago

Spectacular view of the lake. We enjoyed the use of the kayaks and all the games at the cottage. You have to cross a busy road to go to the dock, but it’s worth the price. The cottage was clean. Beds were comfortable. Such a beautiful area to visit!

4.73 out of 5 average rating, 52 reviews

Lake-house Boat Dock, Kayaks, King Bed, Grill etc!

MarcRating, 5 stars3 weeks ago

Couldn’t have asked for more!! Space was clean and comfortable, check in was a breeze and the property was just what we wanted. Thank you for a nice relaxing get away.