Vacation rentals with a kayak in Chautauqua Lake

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Top-rated kayak rentals in Chautauqua Lake

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Top guest favorite

The cabin's exterior is illuminated at dusk, reflecting beautifully on the calm surface of the pond. Surrounding tall trees offer a natural backdrop, enhancing the serene atmosphere of the retreat.

Home in Gerry

Forest Retreat, 90 miles to Niagara Falls.

Welcome to Forest Retreat! We are nestled in the hills of Western New York, 23 miles to Chautauqua Lake and 14 miles to Lily Dale. This unique home is near several wedding venues and the Earl Cardot Overland Trail, which is surrounded by 2,300 acres of state forest. We are located between 2 local ski resorts, and only 87 miles south of Niagara Falls State park. Relax by the fire, kayak, or fish in the 2 acre pond and just enjoy the scenery. We do require a signed waiver to utilize the pond.

LocationOutdoor spacesWifi

4.96 out of 5 average rating, 129 reviews

Top guest favorite

A lakeside cottage is nestled among lush greenery, featuring a spacious deck with outdoor seating. Kayaks are visible on the shoreline, and a wooden dock extends over the calm water, reflecting the home and surrounding trees.

Cottage in Cassadaga

Lakeside Retreat - The Dragonfly Inn & Resort

Relax at my Four-Season lakeside retreat. This family friendly cottage features a spacious loft area with half bath and master bedrooms and bathrooms on the first and lower levels. The first level has a spacious open floor plan with full kitchen, dining area and living room that features spectacular lake views. The lower level amenities include a media/gaming room, recreation room w/coffee bar & laundry. Enjoy the scenery from an expansive deck & patio and swim from your own personal beach.

Outdoor spacesLocationAccess

4.99 out of 5 average rating, 67 reviews

Guest favorite

An outdoor dining table is set for a meal, featuring a neutral table runner and decorative elements. Nearby, a grill is visible, with lake views stretching into the distance. Adirondack chairs are positioned on the lawn, facing the water.

Home in Mayville

Casa Andante - Lakefront Escape

Getaway to Chautauqua Lake year round! Perfect for families and friends to retreat to an idyllic lakefront home. Featuring a large open kitchen with beautiful lake views, patio with outdoor kitchen, fire-pit, 76' of lakefront, and ample gathering space to create memories. Pass time on the lake, visit the infamous Chautauqua Institution, enjoy a front row seat to the beautiful fall foliage, spend the day visiting Peek'n Peak, or snowmobile on the local trails. There is something for everyone!

Outdoor spacesLocationNearby

5.0 out of 5 average rating, 52 reviews

Top guest favorite

Home in Cassadaga

Blue Oar/Luxe Lakehouse/Chautauqua

Welcome to Blue Oar Lakehouse on Cassadaga Lakes! Luxe 4 Bed / 3 full Bath, with stunning views, private dock, and 75 ft beach. Spacious and light-filled, renovated 1925 Craftsman home, perfect for family or group getaways. Located in a quiet, year-round neighborhood just minutes from Lily Dale and The Red House. Dog-friendly. Kayaks, paddle boards, pedal boat, bikes, yard games, grill, firepit on lakefront. If booked, check out our sister property, Blue Canoe (2BR/1BA, right on the water!

ValueOutdoor spacesCondition

5.0 out of 5 average rating, 141 reviews

Top guest favorite

Home in Irving

Lotus Bay Cabin- all seasons oasis

*8-person stand alone hot tub open Dec.-April* *In-ground pool with spill over hot tub & pool house open May 1st, 2026* Winter, Spring is that you? A drink in the above ground hot tub (or pool & hot tub), meals in the fully stocked kitchen, movies on the spacious sectional, reading in the sunroom, bomb-fires under the dark sky & gorgeous sunsets, walks and seasonal swimming along Lake Erie…simply cannot go wrong! Wine country, beaches, ski resorts, Buffalo & Niagara Falls all nearby

ValueOutdoor spacesView

5.0 out of 5 average rating, 236 reviews

Guest favorite

A serene pond is surrounded by lush greenery, reflecting soft hues of pink and blue from the sky during twilight. Grasses and reeds frame the water, creating a peaceful natural environment that invites relaxation and contemplation.

Ranch in Cattaraugus

fire pit•fishing•kids play area on Quiet ranch

The perfect place to reconnect. A space for couples, families or friends, this unique above barn apartment offers a quiet hideaway. Set on 110 scenic acres of forest & pasture, an ideal spot to hike, explore &relax. The property invites you to slow down unwind &take in the natural beauty of your surroundings. Fish, kayak or swim in private onsite pond and creek. Conveniently located: 12 Miles from Ellicottville 45 mins to Buffalo 1 hour & 15 min to Niagara Falls Accommodates 1–5 guests

LocationOutdoor spacesLayout

4.97 out of 5 average rating, 103 reviews

Guest favorite

Home in Ashville

NEW! All Stowed In | Cozy Cottage on CHQ Water

All Stowed In! Some places you visit. This one you stow yourself into. A lovingly updated 1909 cottage tucked into the no-wake zone of Chautauqua Lake, with your own dock, boat lift, kayaks, fire pit and glassy-water mornings. Steps from the historic Stow Ferry and minutes from Bemus Point and Chautauqua Institution. Explore Southern Tier Brewing, wineries, foliage and hiking - or come when the snow flies for skiing, snowmobiling, ice fishing & cozy lake weekends. A 4 season destination.

Outdoor spacesLocationCleanliness

5.0 out of 5 average rating, 5 reviews

Top guest favorite

A wooden dock extends over calm waters, leading toward distant hills under a pastel sky. Reflection creates a serene atmosphere, with subtle textures on the water surface. Boat slips are visible on either side of the dock, enhancing the lakefront experience.

Cottage in Ashville

Cozy lake property get away

Small cottage ( app. 400 sq ft ) on large lake front parcel. The rental is the rear cottage with partial lake front view, quiet neighborhood and large yard. Two miles to Bemus point where there are several restaurants and a grocery store. Chautauqua county voted best small golf town by golf digest. National comedy center in Jamestown. Boat rentals near by. Guests have outdoor dining area and a fire pit. There is a large supply of fire wood also. Chautauqua institution 7 minutes.

Outdoor spacesValueAccuracy

4.95 out of 5 average rating, 168 reviews

Top guest favorite

A charming cottage is visible by the lake, featuring a stone exterior and a gabled roof. Large windows allow natural light to enter, while a small patio with seating is situated under a red canopy. Surrounding trees enhance the natural setting.

Cottage in Findley Lake

Hidden Cove

Beautiful lakefront cottage on Findley Lake. Completely remodeled cozy one-bedroom cottage with two docks, 150 ft. of lake frontage, and boathouse. Tucked away on a quaint woodsy lot, you can enjoy breathtaking sunsets while relaxing around the firepit. Hidden Cove offers a one bedroom with a queen mattress and futon in the living room. The kitchen is fully stocked. Just a few miles from Peak n' Peek resort where you can enjoy skiing, cycling, ziplining, segway tours, and restaurants.

Outdoor spacesLocationKitchen

4.97 out of 5 average rating, 137 reviews

Guest favorite

A charming cottage is depicted with a metal roof and an American flag waving at the front. Two blue chairs are positioned on the patio, overlooking a grassy area leading to the lake, where an orange kayak is secured at the dock.

Cottage in Cassadaga

Lakefront Sunset Getaway on Cassadaga Lake

Welcome to the Cottage! This cottage sits directly on Cassadaga Lake where you can enjoy beautiful sunsets every night from the concrete patio or from the couch. Feel free to go kayaking, fishing, or swimming directly from the dock or shoreline. Perfect for anyone who wants to enjoy lake life for the weekend, week, or month! *NEW* 2 kayaks are available for free use during your stay. No gatherings, events, and/or parties larger than your reservation. Free parking up to 2 cars.

LocationOutdoor spacesCleanliness

4.95 out of 5 average rating, 146 reviews

Top guest favorite

A modern lake house is nestled among tall trees, featuring a spacious porch overlooking the water. The exterior combines dark siding with stone accents, and a small beach area is visible at the shoreline, complemented by a few outdoor chairs.

Home in Cassadaga

Kingfisher Point: Beautiful New Lakeside Home

This stylish new lake house was completed in September of 2022, and we are excited to open it to visitors to the Cassadaga Lake. Our home on Cassadaga Lake rests among the trees of an old growth forest adjacent to protected wetlands. Guests can enjoy the sun setting over the lake each evening from one of two porches facing the lake, or from the kayaks that are available to guests. And yes, Kingfishers are frequent visitors to the lakes as well! (No smoking and no pets allowed).

Outdoor spacesLocationTV

5.0 out of 5 average rating, 101 reviews

Top guest favorite

A charming lake house is set among greenery, featuring a large front deck with seating and flower pots. The blue exterior is complemented by a sloped roof and multiple windows, inviting natural light into the cozy interior. The well-maintained lawn enhances the welcoming atmosphere.

Cottage in Findley Lake

Just another day in paradise

Just another day in paradise Offers a family lake house with a great sunset. Has a large front deck that over looks the lake with gas grill. Large dock with a great swimming area, out door patio with brick fire pit. This cottage has a equipped kitchen with a stove , refrigerator with ice maker , microwave, and dish washer. Only 5 mins from here is peek n peak ski resort . Also located on chautauqua snowmobile trails . Many wineries . 25.00 per stay per dog...... no cats allowed

LocationValueBeach

4.88 out of 5 average rating, 210 reviews