A statue of a man and a woman on a brick pathway with a building in the background.

Town of Chautauqua Holiday Rentals

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Our top choices for Town of Chautauqua holiday rentals

A modern living room with a brick accent wall, a sofa, a bed, and a dining area.

1. Cozy Loft-Pet Friendly-Spacious

Cozy Loft-Pet Friendly-Spacious
Mayville
10.0 out of 10, Exceptional, (4 reviews)
"Great stay. Clean loft and pet friendly.Host was easy to"
United States
Angela W.
The price is AU$340
includes taxes & fees
8 Nov - 9 Nov
Cozy Loft-Pet Friendly-Spacious
A single-story house with a front porch, a small garden, and a driveway.

2. 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, (8 reviews)
"Great property. Tiffany thought of everything. It was all so welcoming and new. Would definitely stay here again. "
United States
Jennifer L.
The price is AU$662
includes taxes & fees
14 Oct - 15 Oct
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
A bedroom with a bed, a desk, a chair, a ceiling fan, and a balcony with a view.

3. Premier St Elmo Unit w Large Balcony over Park

Premier St Elmo Unit w Large Balcony over Park
Chautauqua
10.0 out of 10, Exceptional, (1 review)
"This unit was perfect and just as described in the listing. The owners were very good with communication and helping us be prepared for our trip."
United States
Kristy C.
The price is AU$339
includes taxes & fees
3 Nov - 4 Nov
Premier St Elmo Unit w Large Balcony over Park
A white RV parked in a wooded area with a paved path leading to it.

4. Small camper in the country

Small camper in the country
Dewittville
9.8 out of 10, Exceptional, (21 reviews)
"Had a great time, unfortunately it rained the entire time we were there but the Rv was very clean and the host was amazing. We will definitely come visit again."
United States
Ashley M.
The price is AU$136
includes taxes & fees
9 Oct - 10 Oct
Small camper in the country
A modern kitchen with a central island, stainless steel appliances, and bar stools.

5. Cozy 2-bedroom condo in beautiful Chautauqua Institution

Cozy 2-bedroom condo in beautiful Chautauqua Institution
Chautauqua
The price is AU$634
includes taxes & fees
15 Oct - 16 Oct
Cozy 2-bedroom condo in beautiful Chautauqua Institution
A kitchen with wooden cabinets, a dining table, and a ceiling fan.

6. The Arlington GB: Charming Centrally Located Condo in Chautauqua Institution!

The Arlington GB: Charming Centrally Located Condo in Chautauqua Institution!
Chautauqua
The price is AU$1,012
includes taxes & fees
9 Oct - 10 Oct
The Arlington GB: Charming Centrally Located Condo in Chautauqua Institution!
A house with a porch, a small garden with flowers, and a starry night sky.

7. Fall colors, cozy firepits, and perfect family gathering times await on 5 Acres.

Fall colors, cozy firepits, and perfect family gathering times await on 5 Acres.
Mayville
10.0 out of 10, Exceptional, (40 reviews)
"The home was clean, host responded to requests promptly. This is our 2nd stay and on the list for next time "
United States
Joseph D.
The price is AU$781
includes taxes & fees
14 Oct - 15 Oct
Fall colors, cozy firepits, and perfect family gathering times await on 5 Acres.
A grassy pathway leading to a white RV with a visible logo.

8. Beautiful Camper on a country road.

Beautiful Camper on a country road.
Dewittville
9.0 out of 10, Wonderful, (16 reviews)
"Nice place "
United States
Steve M.
The price is AU$180
includes taxes & fees
12 Oct - 13 Oct
Beautiful Camper on a country road.
Lakefront dining table with seating for 8 around the table

9. Casa Andante - Lakefront Escape

Casa Andante - Lakefront Escape
Mayville
10.0 out of 10, Exceptional, (69 reviews)
"Our family celebrated a beautiful weekend at Casa Adante. The property provided everything we needed, easy check in, serene lake views, proximity to cool places around the lake, and plenty of space. Thank you to the hosts for creating a cozy place where amazing memories were made! "
United States
Georgann F.
The price is AU$1,448
includes taxes & fees
21 Oct - 22 Oct
Casa Andante - Lakefront Escape
A living room with a stone fireplace, a television, and a dining area in the background.

10. Walk out the door, walk onto the beach!

Walk out the door, walk onto the beach!
Dunkirk
10.0 out of 10, Exceptional, (98 reviews)
"Beautiful property and super nice host!"
United States
Ashley F.
The price is AU$463
includes taxes & fees
27 Oct - 28 Oct
Walk out the door, walk onto the beach!
A spacious living area with a dining table, a sofa, and a kitchen with wooden cabinets and a built-in island.

11. 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, (73 reviews)
"A very pleasant stay here. It was peaceful and so nice to sit on the back deck!"
United States
Mary Anne J.
The price is AU$425
includes taxes & fees
14 Oct - 15 Oct
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
A spiral staircase with wooden steps and metal railings, leading to an upper level with a skylight.

12. 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, (64 reviews)
"Peaceful, great location and beautiful interior/decor. Wished we could have stayed longer. Nice proximity to local vineyards and local towns. Our pups also appreciated standing on the overlook and peering out to ever changing Lake Erie."
United States
amy k.
The price is AU$509
includes taxes & fees
20 Oct - 21 Oct
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
A canal with boats, surrounded by residential houses and greenery.

13. Cozy 2 Bedroom Canal Front Cottage With Private Dock

Cozy 2 Bedroom Canal Front Cottage With Private Dock
Ashville
9.6 out of 10, Exceptional, (60 reviews)
"Enjoyed our stay close to all we the areas we were looking to explore"
United States
Chris L.
The price is AU$373
includes taxes & fees
12 Oct - 13 Oct
Cozy 2 Bedroom Canal Front Cottage With Private Dock
A modern kitchen with white cabinets, stainless steel appliances, a black countertop, and a wooden floor.

14. Beautiful Wine Trail 2-BR Rental

Beautiful Wine Trail 2-BR Rental
Westfield
9.8 out of 10, Exceptional, (17 reviews)
"You have the whole house so it is nice and quiet. I stayed here twice this summer and it was very convenient and relaxing. AC works well and the bed is comfortable."
United States
Chihiro
The price is AU$380
includes taxes & fees
20 Oct - 21 Oct
Beautiful Wine Trail 2-BR Rental
A kitchen with a central island, bar stools, a hanging light fixture, and a painting on the wall.

15. Step back in time farm house

Step back in time farm house
findley lake
9.6 out of 10, Exceptional, (101 reviews)
"the host was flexible and accomadating. We had a excellent stay and are gratefull for the clean and tidy beds and breakfast eating area."
United States
yehuda! M.
The price is AU$218
includes taxes & fees
14 Oct - 15 Oct
Step back in time farm house
A modern kitchen with dark cabinetry, a central island, and a dining area with a chair and table.

16. Charming 2BR Cottage · Near Lake Lookout · Wine Tasting Included · Pet Friendly

Charming 2BR Cottage · Near Lake Lookout · Wine Tasting Included · Pet Friendly
Portland
9.6 out of 10, Exceptional, (7 reviews)
"Cute cottage. Perfect location. Very clean and the process was very smooth."
United States
Julianne C.
The price is AU$509
includes taxes & fees
20 Oct - 21 Oct
Charming 2BR Cottage · Near Lake Lookout · Wine Tasting Included · Pet Friendly
A wooden deck with benches and a picnic table, a red building with a white door, and trees in the background.

17. Big Beach Fantastic Lakeview Private Lake and Beach Access Close to Wineries

Big Beach Fantastic Lakeview Private Lake and Beach Access Close to Wineries
North East
10.0 out of 10, Exceptional, (108 reviews)
"Our stay was perfect! The Owner was super communicative and very helpful. The house was beautiful and very clean. They even offered a later checkout due to heavy fog and concerns about road conditions. We plan on booking again."
United States
Margie B.
The price is AU$878
includes taxes & fees
19 Oct - 20 Oct
Big Beach Fantastic Lakeview Private Lake and Beach Access Close to Wineries
A living room with a sofa, a coffee table, a television, and a bookshelf.

18. 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, (48 reviews)
"The house was very comfortable and had everything we needed for our stay. Xinni was quick to respond and was an excellent host. Highly recommend if you are looking for accommodations in the area."
United States
Christine R.
The price is AU$465
includes taxes & fees
16 Oct - 17 Oct
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
A modern kitchen with wooden cabinets, stainless steel appliances, and a granite countertop.

19. 3- Bedroom Apartment at an Award Winning Winery

3- Bedroom Apartment at an Award Winning Winery
Ripley
10.0 out of 10, Exceptional, (34 reviews)
"Great stay at Xinnis as usual! Everything we needed for our quick stay visiting family."
United States
Toni P.
The price is AU$485
includes taxes & fees
10 Oct - 11 Oct
3- Bedroom Apartment at an Award Winning Winery
A spacious living room with a wooden dining table, a sofa, and a staircase with a carpeted handrail.

20. Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14

Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14
Clymer
9.8 out of 10, Exceptional, (91 reviews)
"I would highly recommend staying here. Wonderful condo and property. Created lasting memories and will return."
United States
BRETT H.
The price is AU$559
includes taxes & fees
11 Oct - 12 Oct
Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14
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 Town of Chautauqua Hotel Reviews

Hampton Inn & Suites Jamestown

Hampton Inn & Suites Jamestown

10/10 Excellent
"Great stay"
Jonathan 1-night trip
Posted 21 hours ago
Hampton Inn & Suites Jamestown

Find out more about Town of Chautauqua

Everything you need to know about Town of Chautauqua holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Chautauqua holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Town of Chautauqua holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Town of Chautauqua holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Chautauqua. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Chautauqua holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Town of Chautauqua holiday rentals we have chosen for you start as low as AU$136 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Town of Chautauqua rentals

At Expedia, we put the best Town of Chautauqua holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Town of Chautauqua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Chautauqua holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Town of Chautauqua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.