Vacation rentals with a kayak in Chautauqua County

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Top-rated kayak rentals in Chautauqua County

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Top guest favorite

Vacation home in Asheville

5 out of 5 average rating, 42 reviews

Hidden Gem 2 on the Canal

Spacious house right on the canal that leads to Lake Chatauqua with a beautiful sun porch to enjoy your morning coffee, soak in the stars at the fire pit! Use the private boardwalk to tie off your boat. Relax and read a book on the back patio, kayak or fish the canal, this place is truly paradise! One block away from the playground, and a five-to-ten-minute drive to everything...stores, restaurants, ice cream shops, miniature golf, Chatauqua Institute and much more. You won't be disappointed

Top guest favorite

A two-story home is situated by the water, featuring a covered porch with seating and a dining area under a large umbrella. A private dock with Adirondack chairs extends into the lake, surrounded by lush greenery and a well-maintained lawn.

Home in Asheville

5 out of 5 average rating, 47 reviews

Lakefront Year-round Home w/Dock & Hot Tub

Eagles & herons & beavers- oh my! Adventure awaits your family at this three bedroom, two bath home directly on Chautauqua Lake. Embrace the adventures that the lake has to offer- boating, kayaking, fishing, swimming, exploring or just relaxing on your own dock. Our lakefront home sets 22 feet from the water! On our large deck, cook your catch on the grill, enjoy lakeside dining, pick out your rocking chair, start the camp fire for stargazing, or soak off your worries in the hot tub! Serenity!

Top guest favorite

A serene lakeside view features a wooden dock leading to calm waters, adorned with colorful kayaks. Red and beige Adirondack chairs are positioned nearby on a pebbled shore, beside a small fire pit. Lush trees provide a natural backdrop, enhancing the tranquil atmosphere.

Cottage in Cassadaga

4.98 out of 5 average rating, 44 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.

Top 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, 41 reviews

Casa Andante - Lakefront Getaway

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

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, 134 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

Home in Irving

5 out of 5 average rating, 207 reviews

Lotus Bay Cabin- Pool/Hot Tub/Lake

*Pool, spa & pool house open May 1st, 2025* Summer is that you? Sipping a drink in the in-ground hot tub & pool, preparing meals in the fully stocked kitchen, enjoying movies on the spacious sectional, reading a book in the sunroom, cozy bomb-fires under the stars & strolling down for sandy beach days, sunsets & walks along Lake Erie…simply cannot go wrong! Lake Erie Wine Country, Buffalo & Niagara Falls all within close reach! *8-person stand alone hot tub re-opens Dec. 1st, 2025*

Guest favorite

Cabin in Bemus Point

4.94 out of 5 average rating, 32 reviews

Cozy lakefront cabin with new dock + fire pit

Beautiful Chautaqua lakefront cabin in Bemus Point with large yard, beautiful lake views, big trees and a brand new private dock! Renovated in ‘22 with a brand new bathroom, stainless steel kitchen appliances including a double oven, quartz countertops, new carpet in all bedrooms, new washer & dryer, water filtration system including reverse osmosis tap (same as bottled water) and stone fire pit. Ideal setting for a family vacation any time of year to relax and make memories together.

Guest favorite

A lakefront cottage features a grey exterior with a metal roof, surrounded by greenery. A concrete patio with a table and chairs is visible beside the cottage. A dock extends into the calm water, where two kayaks are positioned on the grass.

Cottage in Cassadaga

4.95 out of 5 average rating, 131 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

Home in Cassadaga

5 out of 5 average rating, 66 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).

Guest favorite

A spacious deck is shown overlooking the lake, framed by lush greenery. A stone table is surrounded by metal chairs, with colorful flower pots decorating the railing. The water's reflective surface and trees enhance the calming atmosphere, creating a serene outdoor setting.

Cottage in Findley Lake

4.88 out of 5 average rating, 176 reviews

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

Guest favorite

A charming boathouse with a textured wood exterior is positioned at the water's edge. A wooden dock extends towards the lake, framed by lush greenery and large rocks that create a natural boundary. The entrance features a simple door, inviting exploration.

Cottage in Findley Lake

4.98 out of 5 average rating, 105 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 pull-out sofa bed. 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.

Top guest favorite

A wooden dock extends into a calm creek, flanked by lush greenery. Two kayaks, one bright green and one beige, are placed on the dock, with additional boats visible in the background. The serene water reflects the surrounding trees, creating a peaceful outdoor setting.

Cottage in Asheville

5 out of 5 average rating, 19 reviews

Creekside Cottage w/Dock, Kayaks/Canoe, & Hot Tub

Welcome to Goose Creek on Chautauqua Lake!! This 3 bed, 1 bath fully equipped cottage on the creek serves as a peaceful getaway year-round. Kayak the calm waters of the creek and enjoy the wildlife along the nature preserve. Fish right from the dock! Just a short paddle or boat ride around the corner and you can watch the sunset out on the lake. In the evening, enjoy a soak in the hot tub and good times around the firepit. Dock your shallow water boat for easy lake access!