New Fairfield Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for New Fairfield holiday rentals

Smart TV, fireplace, books
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Holiday Home in New Fairfield

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
10.0 out of 10, Exceptional, (16)
"Great location and condition. Roome enough for everyone."
United States
Christopher H.
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
Outdoor dining
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Apartment in New Fairfield

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
10.0 out of 10, Exceptional, (34)
"Stunning property!!"
United States
Samantha
The price is HK$1,923
HK$3,455 total
includes taxes & fees
31 Dec - 1 Jan 2026
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Outdoor spa tub
Awesome Lake Home with tons of fun!

Holiday Home in New Fairfield

Awesome Lake Home with tons of fun!
2.0 star property
9.8 out of 10, Exceptional, (7)
"Great spot "
United States
Mike P.
The price is HK$3,497
HK$5,961 total
includes taxes & fees
3 Jan - 4 Jan 2026
Awesome Lake Home with tons of fun!
Exterior
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Camping in New Milford

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
1.0 star property
8.0 out of 10, Very good, (1)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
The price is HK$1,166
HK$1,496 total
includes taxes & fees
8 Jan - 9 Jan 2026
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
Property grounds
Creekside Retreat Tent

Camping in New Milford

Creekside Retreat Tent
10.0 out of 10, Exceptional, (4)
"Absolutely beautiful location and wonderful hosts very romantic spot lots of hiking trails near and on premises me and my husband loved the fact we slept by the water and can hear the water running all night very peaceful and beautiful site ."
United States
yarelis t.
The price is HK$1,166
HK$1,496 total
includes taxes & fees
1 Jan - 2 Jan 2026
Creekside Retreat Tent
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Holiday Home in Shelton

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is HK$933
HK$1,529 total
includes taxes & fees
1 Jan - 2 Jan 2026
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Apartment in Watertown

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
8.6 out of 10, Excellent, (10)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$692
HK$951 total
includes taxes & fees
3 Jan - 4 Jan 2026
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior
Cozy One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (20)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is HK$664
HK$920 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy One Bedroom Apartment Centrally Located in Southbury
Microwave, oven, stovetop, dishwasher
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Apartment in Southbury

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful place. Very clean & welcoming "
United States
Chris
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
Interior
Private Apartment in Southbury 101

Apartment in Southbury

Private Apartment in Southbury 101
9.4 out of 10, Exceptional, (6)
"Great stay. Clean, open space, easy access, and a nice pond in back to bring the dog. Would come back again."
United States
Rooster D.
The price is HK$824
HK$2,148 total
includes taxes & fees
18 Jan - 19 Jan 2026
Private Apartment in Southbury 101
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Holiday Home in Carmel Hamlet

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is HK$1,294
HK$2,758 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Fridge, microwave, oven, stovetop
Private Apartment in Southbury 103

Apartment in Southbury

Private Apartment in Southbury 103
10.0 out of 10, Exceptional, (2)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
The price is HK$785
HK$2,096 total
includes taxes & fees
31 Dec - 1 Jan 2026
Private Apartment in Southbury 103
3 bedrooms, iron/ironing board, travel cot, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms

Holiday Home in Holmes

"Country outside the city " 3 bedrooms 2 full bathrooms
2.0 star property
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is HK$1,462
HK$4,275 total
includes taxes & fees
5 Jan - 6 Jan 2026
"Country outside the city " 3 bedrooms 2 full bathrooms
Interior
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Cottage in Putnam Valley

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.8 out of 10, Exceptional, (23)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,489
HK$3,907 total
includes taxes & fees
4 Jan - 5 Jan 2026
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Outdoor dining
Hoppy Hill Farm House

Apartment in Dover Plains

Hoppy Hill Farm House
9.6 out of 10, Exceptional, (4)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
The price is HK$777
HK$1,495 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hoppy Hill Farm House
Property grounds
Private Apartment in Southbury 102

Apartment in Southbury

Private Apartment in Southbury 102
9.6 out of 10, Exceptional, (4)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
The price is HK$824
HK$2,148 total
includes taxes & fees
13 Jan - 14 Jan 2026
Private Apartment in Southbury 102
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

Apartment in Carmel Hamlet

Charming 1-bedroom apartment in Carmel with WiFi, AC
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,049
HK$2,164 total
includes taxes & fees
31 Dec - 1 Jan 2026
Charming 1-bedroom apartment in Carmel with WiFi, AC
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Holiday Home in Hopewell Junction

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is HK$1,182
HK$2,023 total
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Fridge, microwave, oven, stovetop
Mid Century Modern Studio w/ Full Kitchen - Newly Built

Apartment in Kent

Mid Century Modern Studio w/ Full Kitchen - Newly Built
9.8 out of 10, Exceptional, (10)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is HK$1,515
HK$1,937 total
includes taxes & fees
1 Jan - 2 Jan 2026
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Property grounds
The Hideaway

Apartment in Brewster

The Hideaway
10.0 out of 10, Exceptional, (6)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
United States
Rick C.
The price is HK$1,205
HK$2,459 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Hideaway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top New Fairfield Hotel Reviews

Hotel MTK Mount Kisco

Hotel MTK Mount Kisco

10/10 Excellent
"Very courteous staff. "
Brandt 1-night trip
Posted 3 days ago
Hotel MTK Mount Kisco

Find out more about New Fairfield

Search for holiday rentals in New Fairfield on Expedia! You can easily find your home rentals, villas, holiday apartments in New Fairfield using one of the methods below:

  • View our selection of featured holiday rentals in New Fairfield
  • Use the map to find apartments and other holiday homes in the New Fairfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in New Fairfield while they last

Look no further and take a look at our great range of rental properties in New Fairfield!

Frequently asked questions

Can I find a holiday rental in New Fairfield?

Yes, there are holiday rentals close to the most popular sights in New Fairfield, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that New Fairfield has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This highly rated holiday home rental in New Fairfield offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Some other homes for rent in New Fairfield include Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger and Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more! .

How many holiday rentals are there in New Fairfield?

Choose from 29 Expedia holiday rentals in New Fairfield for a memorable holiday.

What can I see and do in New Fairfield?

Explore the area and family-friendly sights such as Quassy Amusement Park, or get out into nature at a spot like Candlewood Lake. In the wider area, you’ll find Squantz Pond State Park and Bear Mountain Reservation.

What are holiday rentals like in New Fairfield?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in New Fairfield. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips.