Vacation Homes

Vacation homes and condos provide room to spread out, entertain friends, and invite the whole family while having all the conveniences of a second home -- whether you prefer a lakefront retreat or a secluded escape. Find a vacation rental in Chautauqua County NY including Chautauqua Lake vacation homes, ski-out chalets next to area ski slopes, Findley Lake vacation homes, wooded family getaways, Cassadaga Lake vacation homes, spacious retreats inside Chautauqua Institution, or Lake Erie vacation homes. Local real estate companies listed below each maintain portfolios of vacation home rentals that may not be individually represented on this page. 

 

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Aqua Casa
Aqua Casa Vacation Homes
Open June - Oct with possible rentals in November. Homestyle Vacation Rentals. Clean, well-kept homes, and grounds. Offering 4 bedroom, 3 bedroom and 2 bedroom lakefront homes with private piers. Accommodations are suitable…
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Blue Oar Lakehouse beach dock adirondack chairs Cassadaga Lakes
Blue Oar Lakehouse on Cassadaga Lakes
This newly renovated 4 bedroom, 3 full bathroom luxury lakehouse is like a private resort right on Cassadaga Lakes! Property features a private dock with gorgeous new lakefront landscaping with firepit and pea gravel lounge…
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Valley View 1
The Cabins at Farrington Hollow
The Cabins at Farrington Hollow is the perfect place to stay for a variety of reasons. Whether you're looking for a romantic mountain retreat or a place that can accommodate a large group, our luxury cabins go the extra mile…
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Stock Photography - House and Keys
Century 21 -Turner Brokers Real Estate
At Century 21 Turner Brokers, our team of over 40 licensed brokers and agents are honored to be at your service.   Here you’ll find all you need to know about Chautauqua Lake Real Estate, Chautauqua Vacation Homes,…
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charrington
Charrington Creek Lodge
1 mile from Cockaigne Ski Resort. Rustic stone lodge with loft and large fireplace on 360+ acres in beautiful Eastern Chautauqua County, the heart of snowmobile, horseback riding and Amish country. Great for small weekend…
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Chautauqua Area Tranquil Vacation Home Exterior
Chautauqua Area Tranquil Vacation Home
Have fun with the whole family at this stylish place centrally located near the city of Jamestown, Chautauqua Lake, Chautauqua Institution, Chautauqua Mall and numerous restaurants. Your Lakewood retreat awaits at this…
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STAY Chautauqua Heights Manor Exterior
Chautauqua Heights Manor
About a mile from Chautauqua Institution & Chautauqua Lake, Chautauqua Heights Manor is perfect for weddings, family vacations & retreats with accommodations for up to 23 people.
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Chautauqua Luxe Rental kitchen
Chautauqua Luxe Rental
This 4 bedroom is luxe, stylish and modern. Everything was built brand new down to the stud. Free standing bath tub in main bedroom upstairs. Floor to ceiling tiled shower with Ove thick glass doors. Shower is top of the line…
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Dube's Chautauqua Rental
Chautauqua Rentals
3 Lovely apartments located in a renovated 1800’s barn in the quaint village of Westfield, NY. Just remodeled and furnished, there is a 3/2, a 2/1 (ADA access) and a 1/1. Close to Lake Erie beaches, vineyards and…
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Erin's Lodge
Erin's Lodge, LLC
Peaceful fully renovated vacation home (accommodates 6 guests comfortably) located in Ripley, NY on the wine trail. The Lodge is nestled on 10 acres of wooded property and is a unique property as it offers two 360 degree…
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Gracewood Front of House
Gracewood
Gracewood is a newly-renovated, charming century home in Mayville that sleeps 18+ guests. Set on six peaceful acres, the home is a mile from Chautauqua Lake. Surrounded by nature, the house has room to relax: modern kitchen,…
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Green Farm exterior with Chautauqua Lake
Green Farm
Green Farm is a historic mansion located in Lakewood, NY on the shores of Chautauqua Lake. This nearly 10,000 square foot 8 bedroom home was built by millionaire banking and tobacco heir Paul Sorg in 1906. It has been…
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Hadley Bay Summer House
Hadley Bay Summer Home
This is a private 3-bedroom home in Hadley Bay with a wonderful yard (100 ft) leading up to a private dock. There is room for a boat and various other water sports such as swimming, fishing, jet skiing, and canoeing. There is…
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Heather's Inn
Heather's Inn
Chautauqua Institution's newest, most convenient, and most complete accommodations. Four spacious furnished apartments, all with central a/c and heat, private baths, and full kitchens. Located one block from the Amphitheater,…
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Holiday Valley Rentals
Holiday Valley Rental Properties
Offers condominiums, townhouses and chalets with capacity up to 10 people. Summer Real Estate Office Several of the properties are slope side and some are within walking distance to the Village. These units are a great choice…
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Irwin Bay Vacation Homes
Irwin Bay Vacation Homes & Cottages
2 year-round vacation homes located on our lakefront property that are just a short stroll from the lake! Come and enjoy all that Chautauqua County has to offer in every season. “Irwin Blue” has had some recent…
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Lake Chaut Rental Vacation Rental
Lake Chautauqua Rentals & Sales
We offer a variety of fully furnished vacation rentals on beautiful Lake Chautauqua ranging from 2 to 5 bedrooms and priced to fit just about any vacation budget. Our vacation rentals are privately owned lakefront homes…
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Lakeside Meadows exterior with garage
Lakeside Meadows
Step into the tranquility of Lakeside Meadows, your picturesque haven nestled amidst 5 sprawling acres just a stone's throw away from the charming town of Mayville, NY. This enchanting 4-bedroom, 3-bathroom abode is a…
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Lakeview Hotel Accommodations
Lakeview Hotel Accommodations
Accommodations conveniently located near Chautauqua Lake include: A cozy Chautauqua Lake Cottage with a shared patio A downtown Mayville Condo A Waterfront Cottage with dock and Chautauqua Lake access An Entire Home in…
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LightKeeper's Refuge Lakehouse front
LightKeeper's Refuge Lakehouse
The Lightkeeper's Refuge is a vacation rental in Westfield NY, right across the street from the Barcelona Lighthouse, public harbor and beach on Lake Erie. Enjoy our 3 bedroom 1.5 bath cottage with grand balconies and a view…
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Maple Get A Way
Maple Bay Get-A-Way
A beautifully remodeled lakefront three bedroom/two bath home with all the amenities you could ask for! The Maple Bay setting is straight from a postcard! Maple Bay Get-a-Way is available for rental by the week during the…
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Morning Glory Inn aerial view inn and pavilion
Morning Glory Inn
Morning Glory Inn offers soaring ceilings and plush, spacious, private suites perfect for an escape or adventure. Guests will find a wrap-around porch, numerous outdoor amenities, a two-story event barn, satellite TV,…
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New York Rental by Owner Chautauqua Lake
New York Rental By Owner
Ready to browse & book a vacation rental home in Chautauqua area? New York Rental by Owner can help! Our website connects travelers and trusted vacation rental home owners with no booking fees.
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STAY-Peek-Condos-3
Peek'n Peak Resort Vacation Rentals
Peek’n Peak Resort offers seasonal adventures & overnight getaways! Book your stay with overnight accommodations at one of our beautiful mountainside condos! >>Book a Condo at The Peak Find the perfect mix of…
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2355 Waits Corner Road
The PFM House
Discover The PFM House, a perfect country retreat for outdoor enthusiasts! Located between Sherman and Panama, New York, this beautifully renovated farmhouse features 4 bedrooms, 2.5 baths, a remodeled kitchen, an indoor hot…
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The Plum Bush Apartment exterior firepit Adirondack chairs pool
The Plum Bush Apartment
Discover The Plum Bush Apartment, a serene retreat just minutes from Chautauqua Institution. Surrounded by enchanting landscapes, this one-bedroom haven offers comfort and tranquility. Inside, a plush queen-size bed, modern…
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The Plum Bush House exterior
The Plum Bush House
The Plum Bush House is an 1865 Italianate, Victorian farmhouse where guests can retreat and gather within a serene, historic landscape and modern comforts. Enjoy charming common areas amidst towering black locusts and quiet…
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point chautauqua vacation home
Point Chautauqua Vacation Home
A fully insulated home for year round comfort! Sleeps 9, screened porch, patio with grill, wood burning stove, 2 baths/4 Bedrooms, fully equipped kitchen, dryer, and TV. Nestled in the private community of Point Chautauqua on…
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Shadywood Cabin
Shadywood Cabin
Shadywood Cabin is a beautiful newly built home located in a beautiful wooded setting with a large yard just steps away. It's located on 60 acres of privately owned property. The house is a very spacious open floor plan with…
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Splash Suites
Splash Suites
Welcome to our charming Splash Suites nestled in the heart of Bemus Point, NY. This cozy retreat boasts three separate units from which to choose. Suite #1 and Suite #2 provide balconies overlooking the picturesque village…
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St. Elmo
St. Elmo & Chautauqua Area Real Estate
Rentals at the St. Elmo condos, throughout Chautauqua Institution and the Chautauqua Lake area. Vacation real estate sales. Within the St. Elmo are efficiency suites, (one room plus kitchen and bath), one bedroom and two…
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Sunset Bay Guest House
Sunset Bay Guest House
Beautiful guest house on Lake Erie. Right on 135 feet of sandy well-groomed beach with a great deck for Lake Erie sunset viewing. Walk to bars, restaurants, marina, break wall and short drive to local wineries and…
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Sunset Hideaway in Portland
Sunset Lake Houses
Sunset Lake Houses includes several vacation homes along the Lake Erie shoreline and in Lake Erie Wine Country. The year-round vacation homes include: Sunset Hideaway in Portland Sunset Lake Cabin in Ripley Vintage Lakefront…
Tottering House
Tottering House
A fully restored authentic Victorian Carpenter Gothic house located in Point Chautauqua, a community on beautiful Lake Chautauqua, New York. A perfect oasis for couples or families wanting to escape and unwind. The house has…
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Vandyke Agency
VanDyke Agency, LLC
Welcome to the VanDyke Agency LLC! We are a full service real estate broker licensed in New York and Pennsylvania. Our vacation rental department is second to none with a portfolio of beautiful cottages, townhomes, and condos…
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