Vacation rentals in New Fairfield

A scenic view of the lake is framed by a stone patio with seating, offering a tranquil spot to enjoy the surroundings. The family room features wooden beams and large windows that invite natural light, while the exterior showcases a charming lake home with a welcoming entrance and natural landscaping.

5 out of 5 average rating, 41 reviews

Candlewood Isle Cabin ~ Dog Friendly~ Lake ~ Dock

Lake, beach, basketball, tennis, docks, pickle-ball, fishing & 2 playgrounds all within a 5 minute walk. Located on Candlewood Isle, welcome to our centrally-located dog-friendly 2,185 sq ft lake home. 3 bedrooms sleeping 6, central a/c and updated. Watch the sunset over the lake & bbq on the grill. Kitchen is well stocked with a spacious table for entertaining. Enjoy 2 separate work spaces, kids loft area with foosball table & lake access. A dock and/ or golf cart can be arranged for a fee.

4.94 out of 5 average rating, 149 reviews

A rustic black barn is showcased, featuring wooden doors and exterior lighting. A paved driveway leads up to the entrance, bordered by a well-maintained lawn and trees. The surrounding natural landscape enhances the barn's secluded charm.

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.

An outdoor seating area is featured with two ornate egg chairs and a spacious sofa. The furniture is complemented by colorful cushions, and a geometric patterned rug is placed underneath. A stone fireplace is visible in the background, surrounded by trees.

4.97 out of 5 average rating, 77 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.

4.97 out of 5 average rating, 151 reviews

A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

4.95 out of 5 average rating, 207 reviews

A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.

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

Large glass doors open to a serene view of Squantz Pond, framed by lush greenery. A cozy living area features a plush sofa and a glass coffee table, while a workspace is visible in the corner. Soft curtains enhance the natural light streaming into the space.

Cabin in New Fairfield

4.85 out of 5 average rating, 79 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.

4.97 out of 5 average rating, 35 reviews

An outdoor terrace features a round table with metal chairs, situated on a natural stone ledge. A patio umbrella provides shade, while the cottage's charming wooden exterior is framed by lush greenery, enhancing the sense of seclusion and tranquility.

Home in New Milford

OWL's PERCH Candlewood Lakefront Rustic Cottage!

If William Morris and the Brothers Grimm had a love-child cottage, it would be the Owl's Perch. This stylish vintage "fisherman's" cottage perched atop 100' of whaleback granite ledge overlooking Candlewood Lake has a feeling all its own. Cozy and unique, reminiscent of a bygone era of escape-from-the-city summer rustication, this is a perfect snug for a romantic couple or solo-"Thoreau". Descend the stone steps: in 200 paces discover a parklike setting of private lakefront!

A serene view of Squantz Pond is framed by lush greenery, with vibrant trees and neatly trimmed grass in the foreground. The tranquil water reflects the sky, creating a peaceful atmosphere, while a private dock is visible along the water's edge.

4.92 out of 5 average rating, 119 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!

4.98 out of 5 average rating, 99 reviews

An aerial view showcases the Candlewood Lakeview Estate, framed by lush greenery highlighting the surrounding landscape. The expansive lake reflects the sky, while the custom home features a brick exterior. Key outdoor amenities are subtly integrated into the picturesque environment.

Home in Danbury

Lakeview Estate - Chef's Kitchen - NYC Getaway

Stunning lake views from every angle! Gorgeous 3,200 square foot custom home with an open floor plan. Highlights include: * Chef's kitchen with Viking Range, Sub Zero Refrigerator, granite countertops & custom cabinets * Expansive 20x30 stone patio overlooking the lake with a fire-pit, speakers & outdoor lighting * 3 spacious bedrooms and 3 full bathrooms with double vanities, showers & separate bathtubs. * 5 SmartTVs including a 65" TV in the main living area

A patio area is depicted, featuring a wooden dining table surrounded by colorful chairs. An umbrella provides shade, while a cozy seating arrangement is visible nearby. Lush greenery and vibrant flowers enhance the outdoor space, contributing to a serene atmosphere.

5 out of 5 average rating, 9 reviews

Embrace Tranquility: Luxe Retreat Candlewood Lake!

Unwind in style in our freshly renovated lakeside sanctuary. Revel in airy rooms, a cozy fireplace, and an open kitchen ideal for gathering. Grill up delights in the private backyard oasis. Indulge in community perks like the boat ramp, tennis courts, and exclusive beach access. Bring your furry friend along for the ultimate getaway! With hiking trails nearby, immerse yourself in nature's serenity. Escape the ordinary and book your slice of paradise now!

4.88 out of 5 average rating, 153 reviews

A wooden dock extends towards a serene lake, surrounded by green hills. A kayak rests on the shore, inviting exploration. The scene is framed by the branches of a tree, adding a touch of nature to the peaceful waterfront view.

Home in Danbury

Candlewood Lakefront Retreat

This beautiful custom-built lakefront house is located only 90 min from NYC. Surrounded by nature, it is serene and peaceful. This spacious and cozy home has panoramic views from the living room, office, and master. The owners have tastefully updated throughout. If you are looking for a truly unique and peaceful retreat on the lake, come have an al fresco morning coffee, or sunset dinner while sitting outside on the deck gazing at the rippling lake.

4.96 out of 5 average rating, 341 reviews

The outdoor space features a hot tub surrounded by natural greenery, providing a serene environment. A cozy cabin with inviting lighting is visible in the background, while torches are placed nearby to enhance the ambiance. Gravel pathways lead to both the hot tub and cabin entrance.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for New Fairfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in New Fairfield

A serene lakeview is showcased, framed by lush greenery and towering trees. A gentle slope leads down to a private dock, with seating provided for relaxation. The calm water reflects the sky, creating a peaceful atmosphere, inviting moments of tranquility.

5 out of 5 average rating, 5 reviews

Best Candlewood Direct Lakefront has Jul 29-31

A patio dining area is set with a round table and four chairs, shaded by a large red umbrella. Lush green grass surrounds the seating, offering views of the lake and distant hills. A wooden railing delineates the property, enhancing the tranquil lakeside setting.

5 out of 5 average rating, 17 reviews

Charming waterfront oasis on Candlewood Lake

A sandy beach area is depicted, featuring two white Adirondack chairs facing the calm waters of the lake. A small wooden dock extends into the lake's surface, surrounded by lush green hills and a cloudy sky, creating a serene outdoor setting.

4.86 out of 5 average rating, 14 reviews

3 BR Lake House in Gated Candlewood Lake Community

4.86 out of 5 average rating, 7 reviews

A modern guesthouse is set amid lush greenery, featuring large windows that invite natural light. The structure blends seamlessly with the landscape, surrounded by vibrant trees and well-maintained grass. A stone pathway leads toward the entrance, enhancing the tranquil outdoor setting.

Guesthouse in Roxbury

Modern Country

A spacious living room is observed from above, showcasing a light-colored sofa and a round coffee table. Large windows bring natural light into the room, providing views of the surrounding trees. A well-organized shelving unit filled with books lines one wall.

4.71 out of 5 average rating, 34 reviews

Beautiful home near Squantz Pond and Thunder Ridge

Large windows frame a tranquil view of Candlewood Lake, with greenery visible in the foreground. Soft light filters through the trees, creating a serene atmosphere. A wooden table is set beside the windows, enhancing the connection to the outdoors.

Home in Brookfield

4.8 out of 5 average rating, 25 reviews

Lake Candlewood Retreat