Vacation rentals in New Fairfield

Apartment in Greenwood Lake

A front porch is framed by white railings, featuring three white Adirondack chairs positioned for relaxation. Lush greenery surrounds the area, creating a peaceful outdoor space. Steps lead down to a stone pathway, with trees visible in the background.

4.94 out of 5 average rating, 86 reviews

Apartment in Lovely Lake House,Pets welcome!

Love Tree Love Nature Love Lake are welcome! Relax with the whole family and your furbaby at this peaceful place to stay. Just 1 Hour From New York City, Our house in Greenwood lake, NY Surrounded By Natures. Sit at the front porch Enjoys and Relax Lake View, 5 Minutes to Community Lake access, 5 Minutes to Kayak Rental, 10 Minutes Walk to Bus Stop to NYC, Convinent Store Dunkin Donut, Restaurants Near by Boating,Kayaking,Fishing,Skiing, Hiking,Bicycling, Apple and Pumpkin picking and Shopping

5 out of 5 average rating, 121 reviews

Home in Greenwood Lake

Escape to the lake!LAKEFRONT/Hot-tub/1 hour to NYC

Lakefront, fully renovated and ready for guests to experience lake living at its best from the inside out. The modern gas fireplace and cozy sectional sofa make the living room the perfect place to perch over crisp autumn evenings. Or take a steaming soak in the backyard hot tub after a day of hiking or exploring all of neighboring Warwick’s wineries, breweries and local farms.With direct access to the lake from the property our location is ideal for kayaking. All within a 1 hour drive from NYC!

4.96 out of 5 average rating, 56 reviews

Condo in Vernon

New Luxury Ski Condo-2 Full Bathrooms

This newly renovated Great Gorge Village condo, the perfect getaway to be active or just relax with the whole family. There is so much to explore during every season. It's heaven for golfers, leaf peepers, skiers, snowboarders, hikers, bikers and water park explorers. For those looking to relax and unwind it's a great area to explore wineries, breweries and top- notch restaurants. Please note: the unit is located on the second floor. Also, the master bedroom loft suite is up a spiral staircase

4.95 out of 5 average rating, 111 reviews

Home in Lake Katrine

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

4.92 out of 5 average rating, 470 reviews

A spacious wooden deck features a seating area with cozy chairs, a dining table, and an umbrella for shade. Potted plants adorn the space, and a grill is positioned nearby, creating an inviting area for outdoor gatherings.

Home in Woodstock

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Completely Private w/ Exceptional, Expansive Mountain View, All-Seasons Hot Tub and Sauna. Billiards room, Fireplace, Woodstove, Screen Porch, 300 Vinyl records, Full Kitchen, bathtub and Bidet Surrounded by nature, but 2 miles from center of town. Hiking and creek swimming walking distance This property is for Love. La Dolce Vita. The Love of Friends and Family. The Love of Time. Fall in Love here, with the Land and with One-Another. *No checkins are avail Tgiving,Xmas Day, Easter Sunday

4.89 out of 5 average rating, 141 reviews

A vacation house is nestled among tall trees, showcasing a multi-level design. Large windows reflect natural light, providing a connection to the outdoors. A spacious deck is partially visible, blending harmoniously with the surrounding wooded area.

Chalet in Goshen

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

4.94 out of 5 average rating, 114 reviews

A spacious outdoor dining area features a large wooden table surrounded by matching chairs. Sunlight illuminates the area, showcasing a well-maintained yard with a manicured hedge and a small garden shed visible in the background.

Home in Northport

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

4.97 out of 5 average rating, 59 reviews

A lakeside retreat is nestled among lush greenery, featuring a spacious deck with blue seating. A gentle slope leads to the water's edge, where a small area is provided for relaxing. A large tree casts shade over the grassy yard, enhancing the natural setting.

Home in Putnam Valley

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Cottage in Greenwood Lake

4.98 out of 5 average rating, 337 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #33593

A stone patio area features wooden seating and tables, surrounded by vibrant autumn foliage. Colorful trees frame the scene, with glimpses of a pool area in the background under a clear blue sky.

4.94 out of 5 average rating, 145 reviews

Ski-In/Ski-Out @ Mountain Creek-Pool/Hot Tub/Sauna

NEWLY Renovated! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

A water slide extends from a rock formation into a bright turquoise pool. A person is seen mid-leap into the water, while a lifeguard stands nearby under a red and white umbrella. Lush greenery surrounds the area, creating a natural backdrop.

4.92 out of 5 average rating, 356 reviews

Appalachian TOP 4TH FLOOR Studio+ w/amazing views!

Location, location, location! This is a very unique, open concept unit. In lieu of a balcony, it has a huge picture window that allows breathtaking center building panoramic views of the slopes! It's also a top floor unit so extra height ceilings. That open concept continues inside where the walls were minimized leading to the master bedroom having an archway in lieu of a door. The result is a very spacious main living area perfect to gather in front of the fire.

4.88 out of 5 average rating, 102 reviews

A covered outdoor seating area is furnished with a combination of turquoise and brown seating, complemented by decorative pillows. Soft lighting from string lights enhances the space. A swing seat is positioned against the wall, and a small table is centered on the tiled patio.

Home in Mastic

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for New Fairfield vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near New Fairfield's top sights

Squantz Pond State Park30 locals recommend

Stop & Shop29 locals recommend

Down the Hatch22 locals recommend

Bear Mountain Reservation16 locals recommend

Great Hollow Nature Preserve & Ecological Research Center12 locals recommend

Michael Ciaiola Conservation Area11 locals recommend

Other great vacation rentals in New Fairfield

Superhost

An expansive outdoor area showcases a heated pool surrounded by wooden decking. Sun loungers and umbrellas are arranged around the pool, with colorful seating accents visible. Pathways meander through lush greenery, integrating seating and recreational spaces within the tranquil courtyard.

Apartment in Downtown Stamford

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

4.97 out of 5 average rating, 181 reviews

An outdoor deck area is shown featuring several light-colored Adirondack chairs arranged around a stone fire pit. A neatly stacked pile of firewood is positioned against a backdrop of trees, creating a natural setting for relaxation and gatherings.

Home in Millerton

Vacation Home In Millerton

Superhost

A charming two-story white house is surrounded by greenery, featuring a welcoming front porch with rocking chairs. The structure showcases large windows and a shingled roof, with a pathway leading to the entrance. The tranquil setting is complemented by the rustic stone bench in front.

Home in Litchfield County

4.8 out of 5 average rating, 10 reviews

Charming home ready for fun and/or relaxation!

An open living area is presented with a spiral staircase leading to an upper level. A dining table with dark placemats and a vase of fresh flowers is centrally located. Cozy seating options include a textured sofa and an accent chair, while a television is mounted on the wall.

4.96 out of 5 average rating, 74 reviews

Peaceful Mountain Retreat

Superhost

The entrance of Minerals Resort and Spa is showcased, featuring a prominent sign surrounded by vibrant autumn foliage and colorful flower beds. The building's stone accents and unique architecture complement the natural scenery of the lush mountains in the background.

4.73 out of 5 average rating, 111 reviews

200 yds Minerals - great for hotel weddings

Cottage in Greenwood Lake

A wooden home is surrounded by lush greenery and manicured gardens. Flower beds with colorful blooms are visible in the foreground, while the house features a large deck. Mature trees provide a natural backdrop, enhancing the serene outdoor atmosphere.

4.96 out of 5 average rating, 48 reviews

5 bedroom 7 beds Cottage Sauna, Hike, Winery & Ski

A communal hot tub is framed by lush green landscaping, with a yellow umbrella providing shade nearby. Smooth stones surround the hot tub, creating a natural aesthetic, while the clear blue water reflects the sunny sky.

5 out of 5 average rating, 57 reviews

Little Getaway at the Black Creek Sanctuary