
Holiday rentals in New Fairfield
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Top-rated holiday rentals in New Fairfield
Guests agree: these stays are highly rated for location, cleanliness and more.

Ranch in the Woods | A Peaceful Designer Retreat
Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

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!

Awesome Lake Home with tons of fun!
Enjoy your time at this meticulous 4 bedroom 2.5 bath 2003 Colonial in park like setting with a 2 minute stroll to Candlewood lake and docks. A yard filled with fire pit, playground, trampoline, tree house, and 19 ft swim spa. Master bedroom-King Size bed, Guest Bedroom-Full size bed, Kids bedroom 1-Full size bed with twin bunk, Kids bedroom 2-Queen Size bed. If you are interested in bringing more guest during the summer months please check out our add on apartment. airbnb.com/h/addonapartment

Top Side
Welcome to Top Side! Nestled in Holmes, NY, Top Side offers lovely views of Whaley Lake. Whether you're looking for a relaxing getaway or an adventure, you'll find plenty of reasons to fall in love with this spacious apartment which is designed to help you unwind and recharge. The Hudson Valley is brimming with activities and attractions for everyone. From historic landmarks and charming villages to outdoor adventures and local dining, you're never far from something special to experience.

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.

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.

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..

A Lovely Cottage in the Woods (Pool Open May 8!)
Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

The Treecastle at the Roundhouse Homestead
The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Willow Treehouse - secluded, unique, romantic
The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109
Popular amenities for New Fairfield holiday rentals
Stay near New Fairfield's top sights
Other great holiday rentals in New Fairfield

Fully Renovated Rural Barn

Candlewood Knolls Cabin

Candlewood Lakefront - Dock, kayaks, Fire Pit

Candlewood Lake House (Lakefront)

Redding Retreat with Pool

The Tower House

Designers Historic Connecticut Home

The Perch in the Purchase
When is the best time to visit New Fairfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £189 | £184 | £200 | £217 | £295 | £315 | £359 | £315 | £258 | £265 | £284 | £232 |
| 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 |
Frequently Asked Questions
Are there family-friendly vacation rentals in New Fairfield?
New Fairfield has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in New Fairfield?
Experience the best of New Fairfield with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in New Fairfield?
Four-legged friends are welcome in New Fairfield. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in New Fairfield?
Yes! Work meets play with ease at over 50 vacation rentals in New Fairfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in New Fairfield have air conditioning?
Absolutely! We offer over 80 house rentals with air conditioning in New Fairfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in New Fairfield have a kitchen?
Absolutely! We offer over 80 house rentals with a kitchen in New Fairfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in New Fairfield have wifi?
Absolutely! We offer over 80 house rentals with wifi in New Fairfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in New Fairfield have free parking?
Absolutely! We offer over 80 house rentals with free parking in New Fairfield. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in New Fairfield

Total holiday rentals
Explore 100 holiday rentals in New Fairfield

Nightly prices starting at
New Fairfield holiday rentals start at £29 per night before taxes and fees

Verified guest reviews
Over 3,030 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
90 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!
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- House rentals New Fairfield
- Rentals with beach access New Fairfield
- Waterfront rentals New Fairfield
- Rentals with a firepit New Fairfield
- Rentals with a fireplace New Fairfield
- Rentals with lake access New Fairfield
- Pet-friendly rentals New Fairfield
- Family-friendly rentals New Fairfield
- Rentals with a kayak New Fairfield
- Rentals with a patio New Fairfield
- Rentals with a washing machine and dryer New Fairfield
- Rentals with outdoor seating New Fairfield
- Yale University
- Yankee Stadium
- Bronx Zoo
- Thunder Ridge Ski Area
- Fairfield Beach
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Sunken Meadow State Park
- Bash Bish Falls State Park
- Mount Peter Ski Area
- Brotherhood, America's Oldest Winery
- Kent Falls State Park
- Taconic State Park
- Mohawk Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Campgaw Mountain Ski Area
- Yale University Art Gallery
- Sleeping Giant State Park
- Bear Mountain State Park
- Mount Southington Ski Area
- Compo Beach
- Sherwood Island State Park
- Storm King Art Center
- Ski Sundown





