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Holiday Rentals in Chautauqua County

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Top Cities in Chautauqua County

Holiday RentalsHoliday Rentals

Westfield

Westfield

Our top choices for Chautauqua County holiday rentals

Property grounds
Beautiful Camper on a country road.

Beautiful Camper on a country road.

Beautiful Camper on a country road.
Dewittville
9.6 out of 10, Exceptional, (9)
"Nice place "
United States
Steve M.
Beautiful Camper on a country road.
Outdoor dining
Comfortable Camper a few miles off thruway and area attractions. Fire ring wood

Comfortable Camper a few miles off thruway and area attractions. Fire ring wood

Comfortable Camper a few miles off thruway and area attractions. Fire ring wood
1.0 star property
Forestville
8.0 out of 10, Very good, (1)
The price is €95
includes taxes & fees
2 Jan - 3 Jan 2026
Comfortable Camper a few miles off thruway and area attractions. Fire ring wood
Fridge, microwave, oven, stovetop
Step back in time farm house

Step back in time farm house

Step back in time farm house
findley lake
9.6 out of 10, Exceptional, (75)
"Great place to stay! Enjoyed the decor and location."
United States
Thomas B.
The price is €132
includes taxes & fees
5 Jan - 6 Jan 2026
Step back in time farm house
Terrace/patio
Lakefront w Dock, Pet Friendly, Spacious Yard

Lakefront w Dock, Pet Friendly, Spacious Yard

Lakefront w Dock, Pet Friendly, Spacious Yard
2.0 star property
Chautauqua Lake
9.8 out of 10, Exceptional, (13)
"Great location,nice property with a great living space. Had a wonderful visit. Everything as advertised "
United States
Richard C.
The price is €219
includes taxes & fees
6 Jan - 7 Jan 2026
Lakefront w Dock, Pet Friendly, Spacious Yard
Smart TV, fireplace, books
The Refined Retreat

The Refined Retreat

The Refined Retreat
Celoron
10.0 out of 10, Exceptional, (13)
"Very clean and organized. Easy in and out. "
United States
scott r.
The price is €261
includes taxes & fees
5 Jan - 6 Jan 2026
The Refined Retreat
Smart TV
Fabulous 1 bedroom apartment in Jamestown. Close to everything. Pet friendly

Fabulous 1 bedroom apartment in Jamestown. Close to everything. Pet friendly

Fabulous 1 bedroom apartment in Jamestown. Close to everything. Pet friendly
2.0 star property
Jamestown
The price is €208
includes taxes & fees
2 Jan - 3 Jan 2026
Fabulous 1 bedroom apartment in Jamestown. Close to everything. Pet friendly
Property grounds
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.

Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.

Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Dewittville
9.8 out of 10, Exceptional, (59)
"We had a wonderful relaxing time. The house was nice and homey. Will be back next time we visit Lily Dale. "
United States
Anonymous traveller
The price is €267
includes taxes & fees
2 Jan - 3 Jan 2026
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Terrace/patio
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
Portland
10.0 out of 10, Exceptional, (51)
"The stay made for a wonderful girls weekend!"
United States
Christine W.
The price is €292
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
Microwave, oven, stovetop, dishwasher
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery

3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery

3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
Ripley
9.6 out of 10, Exceptional, (33)
"Beautiful location!"
United States
Cheri S.
The price is €291
includes taxes & fees
1 Jan - 2 Jan 2026
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
Fridge, microwave, oven, stovetop
Beautiful Wine Trail 2-BR Rental

Beautiful Wine Trail 2-BR Rental

Beautiful Wine Trail 2-BR Rental
Westfield
10.0 out of 10, Exceptional, (8)
"Very clean, very well appointed and the owners were very accommodating Easy parking and close to all the areas we wanted to go toI would stay there again"
United States
harry w.
The price is €268
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful Wine Trail 2-BR Rental
3 bedrooms, iron/ironing board, WiFi, bed sheets
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
Chautauqua
10.0 out of 10, Exceptional, (4)
"Everything was PERFECT!!! The beds are so comfy, the kitchen was perfectly stocked with everything we needed and the bathrooms were newly renovated and posh. We loved being able to use the whole house - our daughter had her own apartment, which she thoroughly enjoyed. We're looking forward to staying again someday!"
United States
Mindy D.
The price is €334
includes taxes & fees
1 Jan - 2 Jan 2026
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
Private kitchen
3- Bedroom Apartment at an Award Winning Winery

3- Bedroom Apartment at an Award Winning Winery

3- Bedroom Apartment at an Award Winning Winery
2.0 star property
Ripley
10.0 out of 10, Exceptional, (21)
"very nice accommodations and close to North East where other family and friends live."
United States
Pamela N.
The price is €306
includes taxes & fees
1 Jan - 2 Jan 2026
3- Bedroom Apartment at an Award Winning Winery
Smart TV, books
Cozy Colonial in Downtown Westfield, NY

Cozy Colonial in Downtown Westfield, NY

Cozy Colonial in Downtown Westfield, NY
Westfield
10.0 out of 10, Exceptional, (24)
"This is a wonderful home that everyone can enjoy. Spotlessly clean and comfortable, and the hostess is phenomenal. Her communication is top notch and she genuinely cares that you have a great time.This is our second time staying here and it is our “go-to” when visiting the area."
United States
Tammy L.
The price is €304
includes taxes & fees
25 Jan - 26 Jan 2026
Cozy Colonial in Downtown Westfield, NY
Interior
Walk out the door, walk onto the beach!

Walk out the door, walk onto the beach!

Walk out the door, walk onto the beach!
Dunkirk
10.0 out of 10, Exceptional, (78)
"The house was very clean and agreat location for our visit with family "
United States
Ray K.
The price is €416
includes taxes & fees
7 Jan - 8 Jan 2026
Walk out the door, walk onto the beach!
Exterior
Portage Ponds 5 BR/3 Bath close to CHQ, wine trail

Portage Ponds 5 BR/3 Bath close to CHQ, wine trail

Portage Ponds 5 BR/3 Bath close to CHQ, wine trail
Westfield
10.0 out of 10, Exceptional, (24)
"Our stay was wonderful! The house was amazing and the host even better."
United Kingdom
Ashley C.
The price is €587
includes taxes & fees
4 Jan - 5 Jan 2026
Portage Ponds 5 BR/3 Bath close to CHQ, wine trail
Marina
Charming Resort in the Heart of Bemus Village on CHQ Lake

Charming Resort in the Heart of Bemus Village on CHQ Lake

Charming Resort in the Heart of Bemus Village on CHQ Lake
Bemus Point
10.0 out of 10, Exceptional, (198)
"Great location, plenty of space!"
United States
Debbie K.
The price is €441
includes taxes & fees
1 Jan - 2 Jan 2026
Charming Resort in the Heart of Bemus Village on CHQ Lake
Property grounds
Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak

Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak

Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak
Clymer
9.6 out of 10, Exceptional, (10)
"The place was nice and clean and welcoming. "
United States
Caity C.
The price is €365
includes taxes & fees
12 Jan - 13 Jan 2026
Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak
Outdoor dining
Lake Front Home Near Peek'n Peak

Lake Front Home Near Peek'n Peak

Lake Front Home Near Peek'n Peak
Findley Lake
10.0 out of 10, Exceptional, (82)
"This an adorable and comfy house. We enjoyed our stay there immensely. The lake view was amazing. Communication with our host was very good, he was very responsive. "
United States
Kelly T.
The price is €354
includes taxes & fees
12 Jan - 13 Jan 2026
Lake Front Home Near Peek'n Peak
Exterior
Four bedroom/three bath. Ideal Winter getaway. Snowmobile trail access.

Four bedroom/three bath. Ideal Winter getaway. Snowmobile trail access.

Four bedroom/three bath. Ideal Winter getaway. Snowmobile trail access.
Mayville
9.8 out of 10, Exceptional, (23)
"We have amazing family time!!! This house has everything to have fun with the kids!!"
United States
Maria Magdalena Q.
The price is €356
includes taxes & fees
4 Jan - 5 Jan 2026
Four bedroom/three bath. Ideal Winter getaway. Snowmobile trail access.
Exterior
DAY RENTAL ONLY/Picnic Rental -private location, pavilion,pool, restrooms

DAY RENTAL ONLY/Picnic Rental -private location, pavilion,pool, restrooms

DAY RENTAL ONLY/Picnic Rental -private location, pavilion,pool, restrooms
Fredonia
10.0 out of 10, Exceptional, (4)
"16 acres of fun and privacy. Nice picnic grounds."
United States
David M.
The price is €253
includes taxes & fees
5 Jan - 6 Jan 2026
DAY RENTAL ONLY/Picnic Rental -private location, pavilion,pool, restrooms
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chautauqua County Hotel Reviews

La Quinta Inn & Suites by Wyndham Jamestown

La Quinta Inn & Suites by Wyndham Jamestown

10/10 Excellent
"Great that they send you text messages. You can check in online which saves alot of time. The room and entire hotel was very clean. Very important this day in age. Will definitely stay here again if in town. "
Janie 1-night trip
Posted 4 days ago
La Quinta Inn & Suites by Wyndham Jamestown

Find out more about Chautauqua County

Holiday Homes in Chautauqua County

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