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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
4.96 out of 5 average rating, 112 reviews

Forest Retreat, 23 miles to Chautauqua Lake.

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.

Top guest favorite
A clear blue pool is surrounded by a smooth deck, featuring a connected hot tub. Comfortable lounge chairs with vibrant cushions sit under a colorful umbrella in the background, and lush greenery frames the area, enhancing the inviting outdoor space.
Home in Irving
5 out of 5 average rating, 212 reviews

Lotus Bay Cabin- Now Open! Pool/Hot Tub/Beach

*In-ground pool with spill over hot tub & pool house open through Dec. 1st, 2025 *8-person stand alone hot tub opens Dec. 1st, 2025 Autumn, winter, is that you? A cold drink in the in-ground hot tub & pool, meals in the fully stocked kitchen, movies on the spacious sectional, book reading in the sunroom, cozy bomb-fires under the stars & beach strolls for gorgeous sunsets & walks along Lake Erie…simply cannot go wrong! Lake Erie Wine Country, Buffalo & Niagara Falls all within close reach!

Guest favorite
A second-story porch extends across the front of the cottage, featuring wooden railings and ample seating. A gas grill is positioned nearby, with views of the surrounding greenery and lakefront. The area beneath is landscaped with stones and grass, providing a natural setting.
Cottage in Dewittville
4.94 out of 5 average rating, 35 reviews

Lakefront w Dock-Large Deck-Amazing Views-Pets Ok

Take a break and unwind at this peaceful, lakefront oasis surrounded by mature trees. The second story porch offers plenty of room for outdoor dining with views of some of the best sunsets on Chautauqua Lake. You'll enjoy close to 100' of lakefront on Tinkertown Bay directly across from Chautauqua Institution. Bring your boat along to our dock (shared with neighbors) or roast some s'mores at the firepit next to the shore. Our dock will be removed 10/11/25 and is usually installed in early May

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
4.98 out of 5 average rating, 55 reviews

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.

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
5 out of 5 average rating, 43 reviews

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!

Top guest favorite
A charming riverfront home is set against a serene backdrop, featuring lush green lawns and tasteful landscaping. Two white swans are seen gracefully near the water's edge, adding a touch of nature to the picturesque setting.
Guesthouse in Warren
5 out of 5 average rating, 71 reviews

The River House

Come relax in our beautiful riverfront home conveniently located within 10 minutes of downtown Warren. We have created a private two-story, two bedroom retreat within the main home, separate entrance and amenities included. Take in the beautiful views of 2024's River of the Year & The Allegheny National Forest while enjoying your morning cup of coffee on our private dock. Hop on a bike or take a scenic stroll along the river and finish the evening cozied up by the fire under the night sky.

Top guest favorite
The image captures a serene lake view with grassy expanses leading to the water's edge. Two docks are visible in the distance, accommodating boats. A bright red kayak rests on the grass, inviting outdoor activities. The surrounding landscape features lush greenery and gentle hills.
Cottage in Asheville
4.95 out of 5 average rating, 160 reviews

Cozy lake property get away

Small cottage ( app. 400 sq ft ) on large lake front parcel. The rental is the rear cottage with very nice 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.

Top guest favorite
A vibrant autumn landscape is displayed with a modern house set against trees showcasing rich fall colors. A peaceful pond reflects the colorful foliage, while a grassy area leads to the water's edge. Wooden decking extends from the house, providing a connection to nature.
Chalet in Little Valley
4.88 out of 5 average rating, 167 reviews

Privacy on the Mountain, Ellicottville.

62 acres of secluded bliss high in the hills of Ellicottville w/therapeutic views across the valley. Swim in the sparkling spring-fed pond, mountain bike, hike or cross country ski through the private wooded groomed trails. Enjoy the sparkling night stars from the hot tub and kick back with friends at a bonfire. Forget the stress of traditional vacationing, restaurant reviews, & tourist traps. Recharge your battery & enjoy the freedom to reconnect with what and who makes you the happiest.

Guest favorite
The cottage is displayed alongside a private dock, featuring wood decking that extends toward the water. Sunlight brightens the exterior, highlighting a charming structure with a peaked roof and multiple windows. A flag stands proudly nearby, indicating a welcoming atmosphere.
Cottage in Asheville
4.89 out of 5 average rating, 53 reviews

Cozy 2 Bedroom Cottage CanalSide with private dock

Have fun with family and friends at this stylish cottage. Full kitchen, living room and sunroom to enjoy your morning coffee and beautiful sunsets of Chautauqua Lake. Steps away is a deck to kick back. For added convenience, dock your boat at the cottage, too! Includes 2 kayaks and paddles for your use. Top your day off with a BBQ and relaxing fire. Sleeps 6. Pull out sofa, bathroom and laundry on main level. Kids park/field across the street. Minutes away from shopping and attractions.

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
4.98 out of 5 average rating, 118 reviews

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.

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
4.95 out of 5 average rating, 141 reviews

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.

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
5 out of 5 average rating, 86 reviews

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).

Popular amenities for Chautauqua Lake kayak rentals