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Crosby Holiday Rentals

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Our top choices for Crosby holiday rentals

1. Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!

Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
Penn Yan
8.8 out of 10, Excellent, (8 reviews)
"Very peaceful 3 days. Amenities were as expected."
United States
alan
The price is NZ$376
includes taxes & fees
9 Sept - 10 Sept
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!

2. Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake

Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake
PennYan
9.6 out of 10, Exceptional, (163 reviews)
" Nice place. Convenient to nearby attractions. "
United States
Douglas K.
The price is NZ$374
includes taxes & fees
19 Aug - 20 Aug
Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake

3. Chipmunk Cottage | Cozy Lakefront Escape

Chipmunk Cottage | Cozy Lakefront Escape
Penn Yan
10.0 out of 10, Exceptional, (1 review)
"Very clean,Very quaint. Great location for fishing and relaxing. Town's nearby to visit,and no external noise at cottage from neighbors and other rentals nearby."
United States
MaryLou S.
The price is NZ$780
includes taxes & fees
15 Sept - 16 Sept
Chipmunk Cottage | Cozy Lakefront Escape

4. Pet Friendly Keuka Yurt

Pet Friendly Keuka Yurt
Penn Yan
9.6 out of 10, Exceptional, (29 reviews)
"Very pet friendly, great location to many local wineries. Will definitely stay here again. For a longer time."
United States
Ian B.
The price is NZ$528
includes taxes & fees
15 Sept - 16 Sept
Pet Friendly Keuka Yurt

5. Deer Path Off Grid Cabin

Deer Path Off Grid Cabin
Rock Stream
10.0 out of 10, Exceptional, (1 review)
"Everything was much better than expected. The whole experience was outstanding. The Host was Great to work with and very friendly. We have already told several people about our experience. I will definitely be back again. Thank you for a great weekend!"
United States
Steve P.
The price is NZ$305
includes taxes & fees
23 Aug - 24 Aug
Deer Path Off Grid Cabin

6. Finger Lakes Cottage

Finger Lakes Cottage
Prattsburgh
9.8 out of 10, Exceptional, (102 reviews)
"Cute place!"
United States
Jessica W.
The price is NZ$295
includes taxes & fees
10 Sept - 11 Sept
Finger Lakes Cottage

7. Modern Studio - Main St Penn Yan

Modern Studio - Main St Penn Yan
Penn Yan
9.6 out of 10, Exceptional, (15 reviews)
"My girlfriend and i went on our first trip together here. It was very cozy! Was walking distance to all the things we wanted to do. We were planning another trip before the weekend was even over. "
United States
Kevin G.
The price is NZ$478
includes taxes & fees
23 Aug - 24 Aug
Modern Studio - Main St Penn Yan

8. Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016

Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
Penn Yan
9.8 out of 10, Exceptional, (158 reviews)
"The cabin and property was perfect for us, the only negative was a lack of water pressure using the shower."
United States
Jeffrey
The price is NZ$286
includes taxes & fees
26 Aug - 27 Aug
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016

9. Cozy little home located in the Finger Lakes

Cozy little home located in the Finger Lakes
Dundee
10.0 out of 10, Exceptional, (3 reviews)
"We only used the property to sleep in while visiting family locally. It was very clean and had basics."
United States
Heather Z.
The price is NZ$521
includes taxes & fees
18 Aug - 19 Aug
Cozy little home located in the Finger Lakes

10. Wine Country Finger Lakes Escape - Waneta Lake

Wine Country Finger Lakes Escape - Waneta Lake
Hammondsport
9.6 out of 10, Exceptional, (10 reviews)
"My children and I had a great stay!So close to Watkins Glen and Hammondsport!"
United States
Lisa D.
The price is NZ$760
includes taxes & fees
18 Aug - 19 Aug
Wine Country Finger Lakes Escape - Waneta Lake

11. Tempest Ranch Camp is perfect for nature lovers. Close to Watkins Glen.

Tempest Ranch Camp is perfect for nature lovers. Close to Watkins Glen.
Beaver Dams
9.0 out of 10, Wonderful, (2 reviews)
"The property was absolutely beautiful and so quiet and peaceful. Dwayne was nearby and extremely accommodating, friendly, and a great communicator. I will definitely return if I have the chance."
United States
Amy R.
The price is NZ$114
includes taxes & fees
18 Aug - 19 Aug
Tempest Ranch Camp is perfect for nature lovers. Close to Watkins Glen.

12. Hubbs Cellar at JS Hubbs Guest House

Hubbs Cellar at JS Hubbs Guest House
Hammondsport
10.0 out of 10, Exceptional, (8 reviews)
"Very clean, quiet and convenient. Host was very nice and easy to work with as was the check-in, check-out process."
United States
Todd B.
The price is NZ$460
includes taxes & fees
9 Sept - 10 Sept
Hubbs Cellar at JS Hubbs Guest House

13. Tranquil Airstream Nature Escape

Tranquil Airstream Nature Escape
Bath
9.8 out of 10, Exceptional, (9 reviews)
"Was a wonderful getaway. Cozy and perfect and exactly what we were looking for!"
United States
Melinda L.
The price is NZ$435
includes taxes & fees
1 Sept - 2 Sept
Tranquil Airstream Nature Escape

14. Cozy Main St Studio - Penn Yan

Cozy Main St Studio - Penn Yan
Penn Yan
The price is NZ$452
includes taxes & fees
7 Sept - 8 Sept
Cozy Main St Studio - Penn Yan

15. Casita: Near Wineries & Keuka Lake: 100"Projector

Casita: Near Wineries & Keuka Lake: 100"Projector
Bath
10.0 out of 10, Exceptional, (16 reviews)
"Excellent place to stay if you are looking for a secluded getaway with someone you love. Perfect for two people with enough amenities to make your stay relaxing. Communication with the host was fast and helpful. Would definitely recommend and stay here again. "
United States
Donald M.
The price is NZ$594
includes taxes & fees
24 Aug - 25 Aug
Casita: Near Wineries & Keuka Lake: 100"Projector

16. Hammondsport Hideaway

Hammondsport Hideaway
Hammondsport
9.8 out of 10, Exceptional, (69 reviews)
"Great location.small but met our needs."
United States
Helen
The price is NZ$424
includes taxes & fees
27 Aug - 28 Aug
Hammondsport Hideaway

17. Gulf Stream House - Unit 12

Gulf Stream House - Unit 12
Hammondsport
10.0 out of 10, Exceptional, (2 reviews)
"Easy walk to everything Hammondsport has to offer!"
United States
Mike B.
The price is NZ$408
includes taxes & fees
18 Aug - 19 Aug
Gulf Stream House - Unit 12

18. OnTheWater Romantic Cabin-Breathtakng View-Beach Fire Pit!-Still Aval Sep-Oct'26

OnTheWater Romantic Cabin-Breathtakng View-Beach Fire Pit!-Still Aval Sep-Oct'26
Hammondsport
9.4 out of 10, Exceptional, (194 reviews)
"The place was wonderful, views beautiful. Very clean. We enjoyed it very much, very relaxing. Thank you!"
United States
Jessica A.
The price is NZ$1,336
includes taxes & fees
10 Sept - 11 Sept
OnTheWater Romantic Cabin-Breathtakng View-Beach Fire Pit!-Still Aval Sep-Oct'26

19. The Ideal Vacation Location in the Heart of Wine Country

The Ideal Vacation Location in the Heart of Wine Country
Penn Yan
10.0 out of 10, Exceptional, (21 reviews)
"Very clean and accommodating for everyone!"
United States
Tricia B.
The Ideal Vacation Location in the Heart of Wine Country

20. Timber Element 2

Timber Element 2
Hector
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay! Highly recommend!"
United States
Susan S.
The price is NZ$475
includes taxes & fees
24 Aug - 25 Aug
Timber Element 2
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 Crosby Hotel Reviews

Find out more about Crosby

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Crosby holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Crosby. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Crosby. Seeing all the best attractions is bound to make you fall in love with Crosby. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Crosby short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Crosby?

Yes, there are holiday rentals close to the most popular sights in Crosby, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Crosby has to offer?

Keuka East: Spacious & Comfy: This highly rated holiday home rental in Crosby is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Crosby?

While exploring the area, visit family-friendly sights like Finger Lakes Boating Museum, or get outside and enjoy nature at Keuka Lake. Watkins Glen State Park and Keuka Lake State Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Crosby?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Crosby. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for small groups.