Holiday rentals in New Fairfield

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Top-rated holiday rentals in New Fairfield

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Guest favourite

Home in Brookfield

4.98 out of 5 average rating, 124 reviews

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

Superhost

Farm stay in Brewster

4.81 out of 5 average rating, 36 reviews

Crooked Cottage at Lobster Hill Farm

You won’t forget the peaceful surroundings of this unique destination. Less than 60 mins outside of NYC and just off of Rt 684. Fall and Winter activities include: -Hiking With Goats - where you walk a leashed young goat through a guided hike on our 75 acre farm. -Feeding and Milking - join the farmers as they feed hay, refill waters, and milk their herd of dairy goats. Spring activities include: -Hiking with Goats -Feeding and Milking -Baby Goat Snuggling Sessions -Baby Goat Bottle Feeding

Guest favourite

Guest house in Brewster

4.94 out of 5 average rating, 102 reviews

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.

Guest favourite

Home in New Fairfield

4.96 out of 5 average rating, 56 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.

Guest favourite

Flat in Brookfield

4.94 out of 5 average rating, 189 reviews

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.

Guest favourite

Home in Patterson

4.92 out of 5 average rating, 24 reviews

Cozy Lakehouse

Forget your worries in this spacious and serene space on the first and second floors of the house. Enjoy the lake view from the porch while dining. Non-motorized lake activities in the summer and ice fishing on the lake in winter. ThuderRidge ski is 10 minutes away. Enjoy hiking/biking/running and other attractions in Connecticut and New York during your stay. Darryl Hall House, a music venue is 15 minutes away. Danbury Fair Mall is 15 minutes away.

Guest favourite

Cabin in Sherman

4.97 out of 5 average rating, 314 reviews

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, SUP, two inflatable two person kayaks, and two wooden boats are available for use.

Guest favourite

Cabin in New Fairfield

4.98 out of 5 average rating, 261 reviews

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. Find us on IG @thelittlecabins

Guest favourite

Cottage in New Fairfield

4.93 out of 5 average rating, 260 reviews

Sweet Dotti's Cottage on Candlewood Lake - 60M NYC

Charming waterfront 4 Bedroom / 2 BA house on Candlewood lake with private dock and toys. Lake living at its best out your back door. Great yard and updated house for hosting family & friends. Turn Key vacation ~75 minutes / 60 miles from NYC. Screened in Porch, Backyard Patio w/ firepit, Grill and more. Well stocked house with full kitchen, TONS of movies & entertainment, and more.

Guest favourite

Barn in Bethel

4.98 out of 5 average rating, 204 reviews

Escape to a Restored New England Antique Milk Barn

A Bucolic antique farm property in the Fairfield County countryside. Welcome to Connecticut country living at its best! Enjoy the gardens from your private patio, take a dip in the pool, read a book surrounded by fall foliage and retire to your very private suite and relax in the soaking tub. Please note the owners reside on the 4 acre property but give guests the utmost privacy.

Guest favourite

Guest suite in Morris

4.99 out of 5 average rating, 348 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

Guest favourite

Cottage in Danbury

4.97 out of 5 average rating, 114 reviews

Fern Grove Cottage

If you’re looking for tranquility, this is the place for you! This charming cottage is located on a secluded country road. The cottage sits at the back of a gorgeous park-like property, and is near parks with hiking trails. This antique cottage has many modern renovations, providing convenience and comfort while maintaining the historic charm. This is the perfect getaway!