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Featured Holiday Homes in New Fairfield

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hopewell Junction
Located in Hopewell Junction, this vacation home is in the mountains, within a 10-minute drive of Clarence Fahnestock State Park and Hudson Valley Research ...
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Danbury
Located in Danbury, this vacation home is on the waterfront, a 1-minute drive from Candlewood Lake and 7 minutes from Candlewood Plaza Shopping Center.
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

New Fairfield
Located in New Fairfield, this vacation home is on the waterfront, a 1-minute drive from Candlewood Lake and 7 minutes from Squantz Pond State Park.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
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Pet-Friendly Beacon Area Vacation Rental: 6 Acres

Pet-Friendly Beacon Area Vacation Rental: 6 Acres

Lagrangeville
With a stay at this vacation home in Lagrangeville, you'll be within a 10-minute drive of Beekman Golf Course and East Fishkill Community Library.
Pet-Friendly Beacon Area Vacation Rental: 6 Acres
Modern, Magical Woodsy Escape 1 Hour From NYC

Modern, Magical Woodsy Escape 1 Hour From NYC

Putnam Valley
Located in Putnam Valley, this vacation home is on a lake, within a 10-minute drive of Regal UA Cortlandt Town Center and Donald J. Trump State Park.
Modern, Magical Woodsy Escape 1 Hour From NYC
Over Sized Colonial on Private Road.

Over Sized Colonial on Private Road.

Pound Ridge
Located in Pound Ridge, this vacation home is within a 15-minute drive of Pound Ridge Town Park and New Canaan Town Hall.
Over Sized Colonial on Private Road.
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

New Fairfield
Located in New Fairfield, this vacation home is in the mountains, within a 5-minute drive of Candlewood Lake and Squantz Pond State Park.
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Cottage at Sunny Day- Lakeside, views, kayak, dock

Cottage at Sunny Day- Lakeside, views, kayak, dock

Newtown
Located in Newtown, this vacation home is on a lake, within a 5-minute drive of Lake Zoar and Family Health Care Center.
Cottage at Sunny Day- Lakeside, views, kayak, dock
Waterfront Family Retreat on Candlewood Lake

Waterfront Family Retreat on Candlewood Lake

New Milford
With a stay at this vacation home in New Milford, you'll be on the waterfront, just steps from Candlewood Lake and a 3-minute drive from Elephant's Trunk Flea ...
Waterfront Family Retreat on Candlewood Lake
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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.

New Fairfield Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our New Fairfield vacation homes are the perfect way for you to wing it.

Holiday houses in New Fairfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of New Fairfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local New Fairfield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in New Fairfield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of New Fairfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

New Fairfield Holiday Homes essential information

Accommodation
259 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views, Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake, Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger, Pet-Friendly Beacon Area Vacation Rental: 6 Acres, Modern, Magical Woodsy Escape 1 Hour From NYC, Over Sized Colonial on Private Road. , Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!, Cottage at Sunny Day- Lakeside, views, kayak, dock, Waterfront Family Retreat on Candlewood Lake

Top trending hotels in New Fairfield

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

New Fairfield
Located in New Fairfield, this cottage is on the waterfront, within a 10-minute drive of Candlewood Lake and Squantz Pond State Park.
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

New Fairfield
Located in New Fairfield, this vacation home is on the waterfront, within a 10-minute drive of Candlewood Lake and Squantz Pond State Park.
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

New Fairfield
Located in New Fairfield, this vacation home is on the waterfront, a 1-minute drive from Candlewood Lake and 7 minutes from Squantz Pond State Park.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Save an average of 15% on thousands of hotels when you're signed in
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

New Fairfield
Located in New Fairfield, this vacation home is in the mountains, within a 5-minute drive of Candlewood Lake and Squantz Pond State Park.
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Don't see what you're looking for?
See all available properties in New Fairfield
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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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^Subject to availability and chosen travel dates.