
Holiday rentals with outdoor seating in New Fairfield
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in New Fairfield
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub
Step into the stylish and peaceful 3BR 2.5BA cabin in a historic Merryall District close to shops, lakes, hiking trails, farms, and downtown New Milford and Kent. Explore the picturesque area and the exciting attractions, or lounge by the fireplace or the fire pit in the magical yard. ✔ 3 Comfortable Bedrooms ✔ Living Room & Sunroom ✔ Wood Burning Hot Tub ✔ Chef's Kitchen ✔ Office/Library ✔ Books, Vinyls & Games ✔ Porch, Yard & Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry See more below!

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

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.

Renovated, one level home in an excellent location
Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

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.

Comfortable home away from home- near everything
Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

Luxury in the Litchfield Hills
Enjoy this gut-renovated two-floor post-and-beam luxury cottage just outside Kent, CT. Just 9 minutes from downtown Kent and close to the best of Litchfield County, our cottage sits on a serene 3.5 acre property that backs up to protected woodlands. We painstakingly brought the rustic space into the present, with a new kitchenette; bathroom with a massive, spa-like shower; new HVAC; and hotel-like accommodations. Close to Kent School, Canterbury, and great for a romantic getaway.

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!

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..

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

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.

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.
Popular amenities for outdoor seating rentals in New Fairfield
House rentals with outdoor seating

Amazing views of the Brass City

Hillside Views in Hudson Valley

Spectacular Lake Views from Every Room & Garden

Slate Cabin - Stylish Country Escape x Rhinebeck

Belle Meade

Best River View, on Rail Trail in Collinsville!

Architect's Hudson Valley Home in the Woods

Cook House | Modern Cottage w/ Hot Tub & Fireplace
Apartment rentals with outdoor seating

*The Ridge House*

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

Hoppy Hill Farm House

The Hideaway

Hudson River Peaceful Getaway, Explore from here

Private space, with yard

Huckleberry Quarters, the Cozy Redding Retreat.

Special Nest w Private Entrance River View Porches
Apartment rentals with outdoor seating

Meadow View

1856 Trading House w/ walk to water

Hike Minnewaska + Walk to Rail Trail, Food, Drink

Luxury furnished condo. Attached garage. Fireplace

Cozy 3-Bed 2-Bath Condo | Parking and Laundry!

1856 Trading House close to water

Private room in condo

Norwalk Loft with Private Patio
When is the best time to visit New Fairfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $321 SGD | $302 SGD | $321 SGD | $363 SGD | $421 SGD | $546 SGD | $595 SGD | $550 SGD | $450 SGD | $466 SGD | $469 SGD | $394 SGD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Quick stats about holiday rentals with outdoor seating in New Fairfield

Total holiday rentals
Explore 60 holiday rentals in New Fairfield

Nightly prices starting at
New Fairfield holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 2,460 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
60 of New Fairfield holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across New Fairfield rentals

4.9 Average rating
New Fairfield stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Rentals with lake access New Fairfield
- House rentals New Fairfield
- Rentals with a firepit New Fairfield
- Family-friendly rentals New Fairfield
- Rentals with a kayak New Fairfield
- Rentals with a washing machine and dryer New Fairfield
- Rentals with a patio New Fairfield
- Rentals with beach access New Fairfield
- Rentals with a fireplace New Fairfield
- Waterfront rentals New Fairfield
- Pet-friendly rentals New Fairfield
- Rentals with outdoor seating Connecticut
- Rentals with outdoor seating United States
- Yale University
- Bronx Zoo
- Yankee Stadium
- Thunder Ridge Ski Area
- Fairfield Beach
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Mount Peter Ski Area
- Sunken Meadow State Park
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Kent Falls State Park
- Mohawk Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Mount Southington Ski Area
- Taconic State Park
- Yale University Art Gallery
- Bear Mountain State Park
- Sleeping Giant State Park
- Sherwood Island State Park
- Ski Sundown
- Compo Beach
- Opus 40
- Inwood Hill Park




