Chautauqua Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chautauqua vacation rentals

An aerial view of a residential area with multiple buildings, roads, and a large green space.

1. GraftonStay Villas 317-A | Cozy 1BR Timber Ridge

GraftonStay Villas 317-A | Cozy 1BR Timber Ridge
Grafton
$217 nightly
The price is $240
Nov 8 - Nov 9
Total with taxes and fees
GraftonStay Villas 317-A | Cozy 1BR Timber Ridge
A laundry room with a front-loading washer and dryer, a bedroom with a bed and a nightstand, and a hallway leading to another room.

2. McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Jerseyville
10.0 out of 10, Exceptional, (29 reviews)
"So nice we already booked for next year!"
United States
Libby W.
$214 nightly
The price is $226
Nov 15 - Nov 16
Total with taxes and fees
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
A white house with a porch and a large tree in front.

3. Our 80-Acre Farm, Lake, Nature Trail, Bonfires, Starry Nights 2 Miles Grafton

Our 80-Acre Farm, Lake, Nature Trail, Bonfires, Starry Nights 2 Miles Grafton
Grafton
10.0 out of 10, Exceptional, (154 reviews)
"Great place to get away and unwind."
United States
Rex P.
$324 nightly
The price is $358
Nov 15 - Nov 16
Total with taxes and fees
Our 80-Acre Farm, Lake, Nature Trail, Bonfires, Starry Nights 2 Miles Grafton
An outdoor hot tub area with seating and a covered patio.

4. Private Basement - Two King Beds and Hot Tub

Private Basement - Two King Beds and Hot Tub
Saint Charles
9.6 out of 10, Exceptional, (5 reviews)
"Clean. The patio was very comfortable and nice to sit and relax. The beds were also very comfortable."
United States
Beth S.
$291 nightly
The price is $327
Nov 8 - Nov 9
Total with taxes and fees
Private Basement - Two King Beds and Hot Tub
A spacious living area with a dining table, chairs, a sofa, and a fireplace. There is a kitchen area with a refrigerator, stove, and cabinets. The room has large windows and a ceiling fan.

5. Lovely Couples Escape on Mississippi River!

Lovely Couples Escape on Mississippi River!
3.0 star property
St. Charles
10.0 out of 10, Exceptional, (4 reviews)
"The property was clean, easy to access, the property owner was easy to talk to and amazing. Loved staying there and will be staying again next year for the same bike race."
United States
Marina
Lovely Couples Escape on Mississippi River!
43-web-or-mls-Grafton166

6. Main Street Cottage with Hot Tub

Main Street Cottage with Hot Tub
Grafton
9.0 out of 10, Wonderful, (9 reviews)
"We really enjoyed the space!"
United States
Ian P.
$264 nightly
The price is $284
Nov 9 - Nov 10
Total with taxes and fees
Main Street Cottage with Hot Tub
A modern apartment with a living room, kitchen, and dining area.

7. Adorable 2 King Bed Frenchtown Home

Adorable 2 King Bed Frenchtown Home
Saint Charles
10.0 out of 10, Exceptional, (5 reviews)
"Great location. Pet friendly. Perfect space for my wife and I to work remotely. So many great local places in close proximity. Host was quick to answer any and all questions. Would absolutely book again."
United States
Don S.
$300 nightly
The price is $338
Nov 9 - Nov 10
Total with taxes and fees
Adorable 2 King Bed Frenchtown Home
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a wooden herringbone floor.

8. Riverside Home - Modern meets comfort

Riverside Home - Modern meets comfort
Grafton
9.8 out of 10, Exceptional, (76 reviews)
"First, the goat was awesome. They reached out to us giving us instructions for entering the property and made sure we knew he was always available to answer questions. They made communicating very easy. The property is clean, well appointed, and conveniently located. Plenty of hot water, beds are comfortable and there are plenty of towels. We will definitely stay there again."
United States
Robert
$273 nightly
The price is $289
Nov 9 - Nov 10
Total with taxes and fees
Riverside Home - Modern meets comfort
A red building with a black door, a small window, and a doormat.

9. The Crimson Caboose! Unique, one of a kind experience in downtown, Grafton

The Crimson Caboose! Unique, one of a kind experience in downtown, Grafton
Grafton
9.6 out of 10, Exceptional, (7 reviews)
"Had a fantastic trip! We recomend highly!"
United States
Jeremy B.
$363 nightly
The price is $385
Nov 8 - Nov 9
Total with taxes and fees
The Crimson Caboose! Unique, one of a kind experience in downtown, Grafton
A staircase with white railings and a ceiling fan.

10. Amazing Renovated Historic Loft on Main Street

Amazing Renovated Historic Loft on Main Street
St. Charles Historic District
10.0 out of 10, Exceptional, (72 reviews)
"This was a prime spot for downtown activities! Near everything and not far from STL. Would absolutely stay here again!"
United States
Rebecca F.
$248 nightly
The price is $266
Nov 9 - Nov 10
Total with taxes and fees
Amazing Renovated Historic Loft on Main Street
A modern kitchen with dark green cabinets, a stainless steel refrigerator, and a dining area with a dark wooden table and chairs.

11. 3BR Close to Historic Main Street-Low Cleaning Fee

3BR Close to Historic Main Street-Low Cleaning Fee
Saint Charles
$239 nightly
The price is $252
Nov 29 - Nov 30
Total with taxes and fees
3BR Close to Historic Main Street-Low Cleaning Fee
A row of multi-story buildings with commercial storefronts, including a cafe and a restaurant.

12. Dog-Friendly Studio on Historic Main Street

Dog-Friendly Studio on Historic Main Street
St. Charles Historic District
9.2 out of 10, Wonderful, (40 reviews)
"Had a wonderful stay. It was a Monday night so parking was very easy and the room was clean and comfortable. I would recommend this place 100% "
United States
Sarah C.
$195 nightly
The price is $216
Nov 9 - Nov 10
Total with taxes and fees
Dog-Friendly Studio on Historic Main Street
A covered outdoor deck with a table and chairs, a view of a body of water, and a green landscape in the background.

13. GraftonStay Villas 319-B | Charming 2BR/2BA Retreat

GraftonStay Villas 319-B | Charming 2BR/2BA Retreat
Grafton
$352 nightly
The price is $389
Nov 8 - Nov 9
Total with taxes and fees
GraftonStay Villas 319-B | Charming 2BR/2BA Retreat
A modern kitchen with white cabinets, a black refrigerator, and a central island.

14. Cottage on Main st- Low Cleaning Fee

Cottage on Main st- Low Cleaning Fee
St. Charles Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Good location. Decorated very nicely. "
United States
Debbie A.
$259 nightly
The price is $278
Nov 16 - Nov 17
Total with taxes and fees
Cottage on Main st- Low Cleaning Fee
A covered outdoor deck with a table and chairs, a view of a body of water, and a green landscape.

15. GraftonStay Villas 317-B | Charming 2BR/2BA Retreat

GraftonStay Villas 317-B | Charming 2BR/2BA Retreat
Grafton
$352 nightly
The price is $389
Nov 9 - Nov 10
Total with taxes and fees
GraftonStay Villas 317-B | Charming 2BR/2BA Retreat
A spacious living area with a dining table, chairs, a sofa, and a fireplace. There is a kitchen area with a refrigerator, stove, and cabinets. The room has large windows and a ceiling fan.

16. Lovely Couples Escape on Mississippi River!

Lovely Couples Escape on Mississippi River!
St Charles
10.0 out of 10, Exceptional, (30 reviews)
"We had a fantastic stay at the cottage! It was fun to watch the view of the river especially when boats went by. The hosts had everything we could need ready for us. The location was easy to find and a perfect base for exploring the St. Charles area."
United States
Sydney
Lovely Couples Escape on Mississippi River!
A modern living room with a leather sofa, a wooden coffee table, and a leather armchair. There is a painting on the wall and a lamp on a side table.

17. Foundry Flat on Main with Free Parking

Foundry Flat on Main with Free Parking
St. Charles Historic District
10.0 out of 10, Exceptional, (1 review)
"Everything was exactly as described. St. Charles is an awesome place!"
United States
Michael
$271 nightly
The price is $300
Nov 9 - Nov 10
Total with taxes and fees
Foundry Flat on Main with Free Parking
A cozy living room with a brick wall, a white sofa with colorful cushions, a small black table, and a potted plant.

18. Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (123 reviews)
"Great"
United States
Richard W.
$202 nightly
The price is $217
Nov 8 - Nov 9
Total with taxes and fees
Prime Loft of Main Street
A neatly made bed with a stack of folded towels, a bedside lamp, and a ceiling fan in a room with a large window and a wall-mounted artwork.

19. Home Near Main with Pet-Friendly Yard and Office

Home Near Main with Pet-Friendly Yard and Office
St. Charles Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Very close to downtown St. Charles and the Kati Trail. The home is cute and bed is comfortable. Easy check in process and fenced in back yard was nice to have."
United States
Jessica S.
$236 nightly
The price is $262
Nov 9 - Nov 10
Total with taxes and fees
Home Near Main with Pet-Friendly Yard and Office
A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

20. Pet-Friendly Apartment Near Main Street

Pet-Friendly Apartment Near Main Street
St. Charles Historic District
8.8 out of 10, Excellent, (18 reviews)
"Property was as advertised. Perfect for my needs, clean, quiet and convenient. Loved Historic St. Charles. Would recommend anytime! Thank you! "
United States
Brian B.
$250 nightly
The price is $276
Nov 9 - Nov 10
Total with taxes and fees
Pet-Friendly Apartment Near Main Street
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.
View all properties

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Chautauqua Hotel Reviews

A spacious lobby with modern seating, a reception desk, and large windows offering views of the parking area.
Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Airport
St. Ann

10/10 Excellent

Easy convenient to airport
United States
Jane
Reviewed March 17, 2025
Pear Tree Inn St. Louis Airport

Find out more about Chautauqua

Everything you need to know about Chautauqua vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chautauqua vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Chautauqua vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chautauqua vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $215 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chautauqua rentals

At Expedia, we put the best Chautauqua vacation 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 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 Chautauqua vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around 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.

Frequently Asked Questions

Are there vacation rentals in Chautauqua?

Yes, we have vacation rentals near popular local attractions in Chautauqua, or you can go with a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Chautauqua?

HotTub-2br2b-near Historic Main Street: This vacation home rental outside of Chautauqua offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the hot tub in this rental home to help you unwind.

What’s there to see and do in Chautauqua?

While exploring the area, visit family-friendly sights like Raging Rivers Waterpark, or get outside and enjoy nature at Mississippi River. Treehouse Wildlife Center and Grafton SkyTour are a couple of places you'll find in the larger area.

What’s a vacation rental in Chautauqua like?

Vacation rentals are privately owned properties you can book for several days or longer in Chautauqua. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips.