Town of Chautauqua Holiday Rentals: Short-Term Accommodations for Rent

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

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

Mayville

Angela W.

HK$1,790 total

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a bed, a desk, a chair, a ceiling fan, and a balcony with a view.

2. Premier St Elmo Unit w Large Balcony over Park

Chautauqua

Kristy C.

HK$1,736 total

includes taxes & fees

1 Nov - 2 Nov

A single-story house with a front porch, a small garden, and a driveway.

3. 20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

Chautauqua

Jennifer L.

HK$3,077 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with stainless steel appliances, a microwave, and a large island with a sink.

4. Cozy 2-bedroom condo in beautiful Chautauqua Institution

Chautauqua

HK$3,546 total

includes taxes & fees

30 Oct - 31 Oct

A house with a porch, a small garden with flowers, and a starry night sky.

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

Mayville

Joseph D.

HK$4,685 total

includes taxes & fees

1 Nov - 2 Nov

6. Casa Andante - Lakefront Escape

Mayville

Georgann F.

HK$7,439 total

includes taxes & fees

2 Nov - 3 Nov

A living room with a stone fireplace, a television, and a dining area in the background.

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

Dunkirk

Ashley F.

HK$2,535 total

includes taxes & fees

9 Nov - 10 Nov

A kitchen with a central island, bar stools, a hanging light fixture, and a painting on the wall.

8. Step back in time farm house

findley lake

Harry C.

HK$1,178 total

includes taxes & fees

2 Nov - 3 Nov

A spacious living room with a wooden dining table, a sofa, and a staircase with a carpeted handrail.

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

Clymer

BRETT H.

HK$3,253 total

includes taxes & fees

1 Nov - 2 Nov

A spiral staircase with wooden steps and metal railings, leading to an upper level with a skylight.

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

Portland

Suzanne D.

HK$2,846 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with wooden cabinets, stainless steel appliances, and a granite countertop.

11. 3- Bedroom Apartment at an Award Winning Winery

Ripley

Emily Z.

HK$2,748 total

includes taxes & fees

30 Oct - 31 Oct

A living room with a sofa, a coffee table, a television, and a bookshelf.

12. 3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery

Ripley

Wendy M.

HK$2,611 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with dark cabinetry, a central island, and a dining area with a chair and table.

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

Portland

Julianne C.

HK$2,846 total

includes taxes & fees

1 Nov - 2 Nov

A wooden deck with benches and a picnic table, a red building with a white door, and trees in the background.

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

North East

Charles T.

HK$4,611 total

includes taxes & fees

2 Nov - 3 Nov

A large, two-story house with a prominent porch and a sign indicating it is a resort.

15. Charming Resort in the Heart of Bemus Village on CHQ Lake

Bemus Point

Elizabeth N.

HK$4,060 total

includes taxes & fees

30 Oct - 31 Oct

A bedroom with a large bed, a wooden ceiling, a chandelier, a bathtub, and a sign that reads "Lake Side".

16. Bemus Point Vintage Suite w/ Soaking Tub & Kitchen

Bemus Point

HK$3,112 total

includes taxes & fees

30 Oct - 31 Oct

A modern kitchen with white cabinets, stainless steel appliances, a black countertop, and a wooden floor.

17. Beautiful Wine Trail 2-BR Rental

Westfield

Chihiro

HK$2,003 total

includes taxes & fees

5 Nov - 6 Nov

A living room with a dark-colored sofa, a small side table, and a large window offering a view of trees and the sea.

18. Lakefront Cottage with Spectacular Lake Erie Views near boat launch

Brocton

"My husband and I were looking for a quiet escape, and this charming cottage on Lake Erie delivered in every way. The lake views alone are worth the stay. We couldn't stop staring at the water from the moment we arrived.The space is clean, cozy, and thoughtfully put together. Comfy beds and pillows. The updated bathroom was a nice surprise, and the kitchen had everything we needed!Our favorite moment? Sitting by the fire pit at sunset with our two Yorkies, watching the sky turn pink and orange...

Christina B.

HK$3,971 total

includes taxes & fees

30 Oct - 31 Oct

A bedroom with a bed, a chandelier, and a window with curtains.

19. Sleeps 5 Fully Equipped Apartment Near Golf Courses

Corry

James

HK$1,301 total

includes taxes & fees

1 Nov - 2 Nov

A wooden deck leading to a cabin with a small porch and a flag.

20. Peaceful camp in the woods near North East PA

North East

Charles H.

HK$2,334 total

includes taxes & fees

2 Nov - 3 Nov

View all properties

Find holiday rentals that suit your style

Apartments

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Top Town of Chautauqua Hotel Reviews

La Quinta Inn & Suites by Wyndham Jamestown

10/10 Excellent

"Location is excellent. There were no USB receptacles in the room."

Peek'n Peak Resort Trademark Collection by Wyndham

10/10 Excellent

"We had a wonderful time here. The old part of the hotel was - well old! But they moved us to a renovated room and it was so much better. We came for a weekend away (date). It was beautiful here we really enjoyed the live music and camp fires across the rd. The golf course was beautiful and the views were stunning! We would go back!"

Webb's Year Round Resort

8/10 Good

"Room was very clean and comfortable! After a long day driving and little sleep the night before the hot tub experience was a welcome delight which they let me use even though it was late at night! Need to use defoamer for hot tub, for I thought I was in an out of control bubble bath LOL. A problem when using swim suits in a hot tub! they hold a lot of soap which turns into volumes of bubbles! Can't be like Europe and be naked! The only negative was a below subpar breakfast which was very sad! Again being spoiled from traveling Europe. Would stay there again due to exceptional pricing!"

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Town of Chautauqua holiday rentals

1. Cozy Loft-Pet Friendly-Spacious

2. Premier St Elmo Unit w Large Balcony over Park

3. 20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

4. Cozy 2-bedroom condo in beautiful Chautauqua Institution

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

6. Casa Andante - Lakefront Escape

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

8. Step back in time farm house

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

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

11. 3- Bedroom Apartment at an Award Winning Winery

12. 3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery

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

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

15. Charming Resort in the Heart of Bemus Village on CHQ Lake

16. Bemus Point Vintage Suite w/ Soaking Tub & Kitchen

17. Beautiful Wine Trail 2-BR Rental

18. Lakefront Cottage with Spectacular Lake Erie Views near boat launch

19. Sleeps 5 Fully Equipped Apartment Near Golf Courses

20. Peaceful camp in the woods near North East PA

Find holiday rentals that suit your style

Top Town of Chautauqua Hotel Reviews

La Quinta Inn & Suites by Wyndham Jamestown

Quality Inn Dunkirk

Modern 300 ft lakefront with pool

Cobblestone Inn & Suites - Corry

Peek'n Peak Resort Trademark Collection by Wyndham

Chautauqua Harbor Hotel - Jamestown

Webb's Year Round Resort

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

Mayville Getaway w/ Deck: Near Chautauqua Lake!