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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, 118 reviews

Forest Retreat, ride snowmobiles from the house.

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.

Guest favorite
A hot tub is situated in a serene outdoor setting, with clear water reflecting the surrounding greenery. A wooden sauna cabin is visible nearby, featuring a large glass door that allows for natural light. Lush grass and trees frame the area, enhancing the peaceful ambiance.
Cabin in Mayville
5 out of 5 average rating, 5 reviews

The Lake Cabin in the Woods!

Immerse yourself in tranquility at this getaway amidst the woods. Located just a short drive from the renowned Chautauqua Institution (4mins), this location offers an idyllic setting by the lake. The cabin has ample outdoor green space, complemented by a tennis court right behind it. It’s just a 5 min walk to the lake and grants you access to the best boat launch in Chautauqua County, a nature trail that is shared by the community and amazing hottub and infrared sauna! This is the sanctuary!

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, 45 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
Home in Cassadaga
5 out of 5 average rating, 122 reviews

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!

Guest favorite
The living area features two inviting gray sofas adorned with decorative pillows. A coffee table is centered on a geometric patterned area rug. Natural light floods in through large windows, illuminating the space.
Home in Warren
4.87 out of 5 average rating, 103 reviews

River View Getaway

This spacious home offers a peaceful getaway on the outskirts of town with a birds eye view of the Allegheny River. You will find easy access to many water activities and just a stone throw away is a public boat launch and dock. Allowing you and other guests to take a quiet stroll to see the white swans along the river. The home is only a short drive to the heart of the city and Allegheny National Forest where you can find outdoor activities and trails as well as many delicious restaurants.

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.

Guest favorite
A serene hot tub sits in a snowy landscape, steam rising gently as the sun sets over distant hills. The surrounding area is blanketed in fresh snow, with silhouettes of trees visible in the background.
Chalet in Little Valley
4.86 out of 5 average rating, 174 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.

Top guest favorite
Home in Irving
5 out of 5 average rating, 218 reviews

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

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
4.87 out of 5 average rating, 54 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.

Guest favorite
The cabin is set against a lush green lawn, showcasing a spacious yard. The exterior features dark wooden siding and large windows, providing a welcoming view. A picnic table is positioned nearby, inviting outdoor gatherings. The area is surrounded by trees, adding to the natural ambiance.
Cabin in Bemus Point
4.95 out of 5 average rating, 41 reviews

Cozy lakefront cabin with new dock + fire pit

Beautiful Chautauqua 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 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.

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
4.87 out of 5 average rating, 195 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

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