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

Cozy Scenic New England rural retreat hike & kayak
Cozy and private studio in attached guest house on 3 bucolic acres w/pond. Two free kayaks parked by the lake town beach (only 3 miles away). Self check-in with private entrance. Enjoy scenic views of pond and farms from deck & patio with your own grill & fire pit. Mosey along our scenic road to nature preserve. 3 miles to quaint town with restaurants & coffee. Close to Appalachian Trail & other great hiking. Family friendly beach on Lake nearby. Pets welcome. Inquire min stay requirements.

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.

Cozy Lake Cabin
Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets in any temps from inside or out, or coffee in the tree hut! Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes COMPLIMENTARY Firewood, NO CLEANING/PET FEES🐕

Oscaleta Guest House: Lakefront Cabin
Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

Waterfront Lake House
Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Private Beach, Paddle Board, Swim
Escape daily stress at Deer Ridge Cabin CT, a bright and airy retreat with all amenities. Enjoy the private beach and paddleboarding at the lake, a 4-minute walk away! or exploring nearby hiking trails. Only a 10-minute drive to downtown Lichfield to indulge in great restaurants and shopping. Experience local wineries. Conveniently located 2 hours from NYC, this peaceful cabin offers a quick escape to nature while being close to everything! Deer Ridge Cabin CT is your perfect getaway!

Cozy Cottage |Quintessential CT | Pet Friendly
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.

Cozy Oasis | Lakefront with Stunning Sunset Views
It’s the Lakefront Paradise you’ve been searching for: Escape to Cozy Oasis where peaceful waters meet modern comfort! Wake to stunning views, spend the day kayaking around the lake, and unwind with breathtaking sunsets from your private deck. This pet-friendly retreat offers high-speed WiFi for remote work, fully equipped kitchen for home-cooked meals, and cozy entertainment spaces. Perfect for romantic getaways or family adventures - your serene lakeside escape awaits!

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..

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.
Popular amenities for kayak rentals in New Fairfield
House rentals with a kayak

The Katalpa House -by the beach

Perfect New Paltz Location!

Lakefront Escape: Beach Access, Firepit, Kayaks!

Creekside Cottage

Waters' Edge on the Esopus

River Cottage in Weston, CT

3 Bedroom Beach House with Hot Tub!

15% off, private pond, BBQ, 4 min to village
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

Hudson Valley Lakefront Cottage | Nature Escape

Cheerful 3 Bedroom Cottage with Fire Place
Cabin rentals with a kayak

Luxury Scandi Lakeside Cabin with Woodfired Sauna

Modern Nordic Designed Cabin

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
When is the best time to visit New Fairfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £174 | £155 | £143 | £248 | £311 | £313 | £358 | £367 | £241 | £267 | £258 | £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 |
Quick stats about holiday rentals with a kayak in New Fairfield

Total holiday rentals
Explore 20 holiday rentals in New Fairfield

Nightly prices starting at
New Fairfield holiday rentals start at £66 per night before taxes and fees

Verified guest reviews
Over 1,380 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 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
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Rentals with lake access New Fairfield
- Rentals with a patio New Fairfield
- Rentals with a fireplace New Fairfield
- Rentals with a firepit New Fairfield
- Pet-friendly rentals New Fairfield
- Rentals with beach access New Fairfield
- Family-friendly rentals New Fairfield
- House rentals New Fairfield
- Rentals with outdoor seating New Fairfield
- Waterfront rentals New Fairfield
- Rentals with a washing machine and dryer New Fairfield
- Rentals with a kayak Connecticut
- Rentals with a kayak United States
- Yale University
- Yankee Stadium
- Thunder Ridge Ski Area
- Fairfield Beach
- Bronx Zoo
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Sunken Meadow State Park
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Mount Peter Ski Area
- Kent Falls State Park
- Taconic State Park
- Mohawk Mountain Ski Area
- Yale University Art Gallery
- Bear Mountain State Park
- Powder Ridge Mountain Park & Resort
- Campgaw Mountain Ski Area
- Sleeping Giant State Park
- Compo Beach
- Mount Southington Ski Area
- Storm King Art Center
- Sherwood Island State Park
- Ski Sundown





