Holiday rentals with a kayak in Chautauqua County

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.

Outdoor spaces · Location · Amenities

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 spaces · Location · Comfort

Cozy Off-Grid Cabin with generator & pond

Unplug and reconnect with nature at our cozy off-grid cabin, nestled in the woods - adjacent to nearly 1000 acres of state land - perfect for those seeking peace and adventure. This retreat runs on generator power and offers the simple pleasures of quiet mornings, star-filled nights, and nature outside your door. The cabin includes: • A comfortable queen bed & pull out sofa • A wood-burning stove for warmth and ambiance. • A propane stove, running hot water • No Wi-Fi, no distractions

Outdoor spaces · Location · Indoor spaces

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!

Outdoor spaces · Location · Amenities

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

Location · Outdoor spaces · Pool

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.

Location · Outdoor spaces · Indoor spaces

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.

Location · Outdoor spaces · Heating

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.

Location · Value · Decor

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.

Location · Value · Backyard

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).

Location · Outdoor spaces · Walkability

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

Outdoor spaces · Location · Sleep quality

Blue Canoe/Upscale Lake Cottage/Chautauqua

Welcome to Blue Canoe Lake Cottage on Cassadaga Lakes! This small, 2 Queen Bedroom/1 Full Bath, newly renovated, open-concept, light-filled cottage offers 125 ft of private waterfront, a gated covered porch, & thoughtful details throughout. Enjoy 2 kayaks, 2 paddle boards, a pedal boat, 4 adult cruiser bikes, fire pit, & propane grill. Dog-friendly & perfect for up to 4 adults — luxury on the lake awaits! If booked, check out our sister property, Blue Oar (4BR/3BA, lakefront!

Outdoor spaces · Location · Biking