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, 85 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, 119 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!

5 out of 5 average rating, 54 reviews

A modern lakeside house features expansive glass windows that offer views of Greenwood Lake. The exterior is framed by lush greenery, and a patio with lounge chairs provides outdoor relaxation. Natural landscaping enhances the tranquil atmosphere surrounding the property.

Home in Greenwood Lake

Explore a Luxurious Lakefront Dream Home

Discover your luxury haven on the serene shores of Greenwood Lake. Boat, swim, kayak, and bask in summer's glory. Fall brings vibrant foliage and fireside coziness. Winter offers skating in the frozen lake and skiing in the nearby mountains while spring blooms with its incredible beauty. Your perfect getaway, where modern comfort meets natural beauty. A quick 45-minute escape from the city with super high-speed internet for your work needs. Book now for an unforgettable escape! Permit N. 23-225

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.

4.89 out of 5 average rating, 141 reviews

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.

4.79 out of 5 average rating, 43 reviews

Two comfortable chairs are positioned on a spacious porch, offering a clear view of the beach and ocean. The horizon is visible in the distance, with calm waters under a blue sky dotted with clouds.

Home in West Haven

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

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.

4.96 out of 5 average rating, 156 reviews

A sunlit interior features large windows framing expansive mountain views. The space contains wooden beams and a mix of seating, including stylish chairs and a dining table. Elegant dishware is displayed on a sideboard, enhancing the cozy cabin ambiance.

Cabin in Boiceville

Catskills Cabin Surrounded by Mountain Views+Spa!

Location is Everything! Our 3BR Catskills home is surrounded by breathtaking mountain views, and close to all including Woodstock Village, Phoenicia, Rivers, Hikes, Breweries, Ski Areas and more. Home is set high on a ridge overlooking nature from all angles on 3 private acres of land. Enormous brand new deck facing mountains with fire pit, grills. Perfect location for exploration. Tastefully decorated with brand new beds and furniture, fully stocked kitchen. Town of Olive STR-22-12.

4.97 out of 5 average rating, 58 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.

5 out of 5 average rating, 60 reviews

Home in Farmington

Lake Escape: Lake Cottage Charm, Lake Front, AC

Direct lakefront access with gorgeous views on a private lake. This beautiful 1930's lakefront cottage was fully renovated and reimagined by its owners in 2021. Custom architectural trim and details can be found throughout blending this homes' heritage with modern amenities. 2 bedrooms, eat-in kitchen and window seat nook, 2 full baths, custom barn doors and cabinetry, a reimagined sunroom, beautiful views on 100' of accessible lake frontage with outdoor patio, 1 mile from town center.

Cottage in Greenwood Lake

A contemporary open-concept kitchen and living area features large windows that frame scenic views. A central dining table complements the kitchen with dark cabinetry and modern appliances. A comfortable couch with decorative pillows enhances the inviting space, while a vibrant potted plant adds natural greenery.

4.98 out of 5 average rating, 336 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

4.9 out of 5 average rating, 99 reviews

A charming building is illuminated by soft evening light, surrounded by blossoming trees adorned with twinkling lights. Outdoor seating is visible, inviting guests to enjoy the vibrant atmosphere of the town. The sky transitions to a serene twilight blue, enhancing the scene.

Guest suite in Branford

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

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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

Apartment in Downtown Stamford

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.

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

4.94 out of 5 average rating, 32 reviews

A serene bedroom features a spacious bed adorned with a colorful blanket. A warm-toned lamp stands beside a wooden nightstand. Natural light floods the room through large windows and a skylight, illuminating a stone fireplace and providing a view of the outdoors.

Home in New Milford

Serene Country home 24 mi Mohawk ski area

4.86 out of 5 average rating, 21 reviews

Home in Ellenville

Cozy 5 Bedroom Escape in ellenville ny

4.94 out of 5 average rating, 32 reviews

The rear exterior of the house is visible, surrounded by lush greenery. A seating area with wooden adirondack chairs encircles a fire pit, and a hammock is positioned nearby. Large windows illuminate the interior, providing a sense of openness and connection to nature.

Home in Hurley

Spacious 4-bed,heat swim pool,new jaccuzzi,fire pt

4.82 out of 5 average rating, 95 reviews

Home in Cornwall

State Forest Getaway

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