
Vacation rentals with a kayak in New Fairfield
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Top-rated kayak rentals in New Fairfield
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Modern Nordic Designed Cabin
Newly designed Modern Nordic Cabin. Escape to the tranquility of the mountains and lakes. The Nordic cabin is modern with high-end finishes throughout. The open concept living area features a fireplace, waterfall shower, vaulted ceilings, and large windows that offer stunning views of the surrounding forest and lake. Getting to and from NYC is easy. There is a bus stop down the street and a train station 15 minutes away. Perfect for a convenient getaway from the city Warwick town Permit 34469

Welcome to The Boathouse! Waterfront/Boats/Hot tub
Perched on the water’s edge, you’ll look down from this bright, modern post at an expanse of winding river and broad tree-lined meadows. Let the mellow current and enveloping natural setting satisfy and soothe your senses. This special place is close to everything, making it an ideal launchpad to all the Hudson Valley has to offer. Kingston, New Paltz and Rosendale are all ten minutes away, surrounding you with a plethora of hiking trails, climbing, dining, drinking, entertainment and shopping.

Cozy Cabin, Fireplace, Ski Nearby
Escape to Deer Ridge Cabin, a serene & cozy retreat designed to help you unwind. Relax by the warm glow of the fireplace or venture out to enjoy nearby skiing & tubing at Mohawk Mt. and Mt. Southington. Explore scenic hiking trails, indulge in local wineries, or visit Litchfield just 10 minutes away for fantastic dining & boutique shopping. Located only 2 hours from NYC, this peaceful cabin offers the perfect winter escape to nature while keeping you close to it all. Your perfect getaway awaits!

Luxury Lake House Sauna 1h From NYC
Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

Lakefront Cottage near Hudson Valley
Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

Upstate Daydreamers Guest Suite
A spacious 3-room private suite for 1-2 guests. The vibe is cozy, quiet, safe, peaceful, comfy — unwind and make yourself at home! Explore our 14 acres of lush forest and creeks, take a bubble bath in the clawfoot tub, soak in the jacuzzi, play mini pool, and collect fresh organic eggs from the chickens. Free on-site parking, excellent cell reception & wifi. Please note, we're no longer serving breakfast - visit our restaurant Ace of Cups (inside Tubby’s) & receive free dumplings instead!

Cozy Getaway | Pet Friendly | Amazing Location
Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

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..

Lakeside Private Guest Suite
Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own lounging/dining area. Guests have their own separate entrance & parking space(s). Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing & just 10 minutes to Washington Depot. We've recently made some updates in response to guests' feedback!

Candlewood Lakefront Retreat
This beautiful custom-built lakefront house is located only 90 min from NYC. Surrounded by nature, it is serene and peaceful. This spacious and cozy home has panoramic views from the living room, office, and master. The owners have tastefully updated throughout. If you are looking for a truly unique and peaceful retreat on the lake, come have an al fresco morning coffee, or sunset dinner while sitting outside on the deck gazing at the rippling lake.

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.

Lake Cabin with Hot Tub, Fire pit and Kayaks
Named one of the Best Airbnbs in Connecticut by Business Insider, The Little Lake Cabin is a cozy Connecticut lake cabin perfect for relaxing, hiking, and reconnecting with nature. Just steps from Candlewood Lake and Squantz Pond State Park, enjoy kayaking, evenings by the fire pit, or a soak in the hot tub under the stars. Your peaceful New England getaway awaits, ideal for couples, friends, and nature lovers alike.
Popular amenities for New Fairfield kayak rentals
House rentals with a kayak

Beachfront house on Long Island Sound

Crystal Wave LakeHouse

The Katalpa House -by the beach

Whispering Pines: Secluded Retreat near town

Waters' Edge on the Esopus

Aster Place

3 Bedroom Beach House with Hot Tub!

House on Candlewood Lake
Cottage rentals with a kayak

Private Lake House 1 Hour to NYC & Near Westpoint

Cottage with Private Deck on 8 acres of Woods

Waterlily Lakehouse - Modern+Waterfront+Retreat

Longview Lakehouse - 5 min walk to private beach

Sunset Cabin Modern Home Kayak FirePit Lake Access

Be in Nature at this Gorgeous Riverfront Cabin

Waterfront, Wooded Cottage on Candlewood Lake

Charming Fairfield Beach Cottage
Cabin rentals with a kayak

Luxury Scandi Lakeside Cabin with Woodfired Sauna

Cascade-Cabin

Cozy Cabin with Pond on Six Acres

Lakefront Log Cabin

Rustic Pond Cabin: Nature, Stars & Serenity

Design-Forward Riverfront Cabin on 120 Acres

Private Woodstock Getaway w Hot Tub

Lakeside Cottage: Boulder's Bluff
When is the best time to visit New Fairfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ841 | ﺩ.ﺇ823 | ﺩ.ﺇ804 | ﺩ.ﺇ1,238 | ﺩ.ﺇ1,553 | ﺩ.ﺇ1,561 | ﺩ.ﺇ1,789 | ﺩ.ﺇ1,833 | ﺩ.ﺇ1,201 | ﺩ.ﺇ1,164 | ﺩ.ﺇ1,131 | ﺩ.ﺇ1,098 |
| 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 vacation rentals with a kayak in New Fairfield

Total vacation rentals
Explore 30 vacation rentals in New Fairfield

Nightly prices starting at
New Fairfield vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 1,340 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of New Fairfield vacation rentals include wi-fi 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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- Rentals with a fire pit New Fairfield
- Pet-friendly rentals New Fairfield
- House rentals New Fairfield
- Rentals with a fireplace New Fairfield
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- Rentals with a kayak Connecticut
- Rentals with a kayak United States
- Yale University
- Yankee Stadium
- Fairfield Beach
- Bronx Zoo
- Thunder Ridge Ski Area
- New York Botanical Garden
- Minnewaska State Park Preserve
- 168th Street Station
- Catamount Mountain Ski Resort
- Sunken Meadow State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Mount Peter Ski Area
- Brotherhood, America's Oldest Winery
- Mohawk Mountain Ski Area
- Bear Mountain State Park
- Mount Southington Ski Area
- Sherwood Island State Park
- Taconic State Park
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Yale University Art Gallery
- Opus 40
- Compo Beach




