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Vacation Rentals in Town of Italy

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Our top choices for Town of Italy vacation rentals

A house with a front porch, a door, and a window. There are potted plants and flowers around the porch.

1. Amazing Stargazing Retreat

Amazing Stargazing Retreat
Naples
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful home and property. Very clean, very quiet. The amenities were lovely and allowed for a restful getaway. Easy communication with host. Definitely recommend!"
United States
Becky H.
$480 nightly
The price is $518
Sep 30 - Oct 1
Total with taxes and fees
Amazing Stargazing Retreat
A waterfall cascading over rocks into a pool, surrounded by greenery.

2. 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, (164 reviews)
"Great experience while wine testing in Finger Lakes - staying at the real cabin, with all the modern conviniences with a twist. Very comfortable bed and cute porch with. We really enjoyed the fire pit after wine testings and morning stroll to the waterfall on the trail just across the river. Highly recommend this very unique house."
United States
Alissa
$151 nightly
The price is $169
Oct 7 - Oct 8
Total with taxes and fees
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
A cozy cabin interior with a sectional sofa, wooden ceiling, white cabinets, and a kitchenette.

3. Finger Lakes Cottage

Finger Lakes Cottage
Prattsburgh
9.8 out of 10, Exceptional, (102 reviews)
"Cute place!"
United States
Jessica W.
$147 nightly
The price is $164
Oct 12 - Oct 13
Total with taxes and fees
Finger Lakes Cottage
A living room with a brown leather sofa, a wooden coffee table, a TV mounted on the wall, and a window with blinds.

4. Beautiful Tiny home Near The Lake

Beautiful Tiny home Near The Lake
Canandaigua
2.0 out of 10, (1 review)
"Owner never sent check/in information and never responded to calls or messages. So we never even saw the inside. Don’t book with this place!"
United States
Chrissy D.
$88 nightly
The price is $94
Oct 7 - Oct 8
Total with taxes and fees
Beautiful Tiny home Near The Lake
Living area

5. Beautiful Newly Renovated 1900s Farm House On 9 Acres

Beautiful Newly Renovated 1900s Farm House On 9 Acres
Rushville
10.0 out of 10, Exceptional, (1 review)
"Beautiful, private, place. We loved the outdoor fire. The bed was very comfortable. We had everything we needed."
United States
ERIC W.
$185 nightly
The price is $207
Oct 1 - Oct 2
Total with taxes and fees
Beautiful Newly Renovated 1900s Farm House On 9 Acres
A modern kitchen with a large island, a sink, and a window overlooking a yard.

6. 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
8.6 out of 10, Excellent, (10 reviews)
"Very peaceful 3 days. Amenities were as expected."
United States
alan
$187 nightly
The price is $210
Oct 6 - Oct 7
Total with taxes and fees
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
A yurt interior with a round ceiling, a mounted television, a wooden barrel, and a small kitchenette.

7. Pet Friendly Keuka Yurt

Pet Friendly Keuka Yurt
Penn Yan
9.6 out of 10, Exceptional, (30 reviews)
"Such a fun yurt and a peaceful location! We loved the proximity to activities and then relaxing with a glass of wine on the little balcony!"
United States
Sharon
$210 nightly
The price is $212
Oct 1 - Oct 2
Total with taxes and fees
Pet Friendly Keuka Yurt
A grassy area with two white Adirondack chairs and a black pot, surrounded by trees and a field.

8. 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.
$161 nightly
The price is $180
Sep 30 - Oct 1
Total with taxes and fees
Deer Path Off Grid Cabin
A living room with a sectional sofa, a fireplace, and a large window.

9. Ideal location for adventure all year round

Ideal location for adventure all year round
Naples
10.0 out of 10, Exceptional, (7 reviews)
"house was clean, quiet area, perfect for my one night stay for a wedding"
United States
Alexis M.
$150 nightly
The price is $161
Oct 19 - Oct 20
Total with taxes and fees
Ideal location for adventure all year round
A modern building with large windows, a table, and an umbrella.

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

Casita: Near Wineries & Keuka Lake: 100"Projector
Bath
10.0 out of 10, Exceptional, (16 reviews)
"Fantastic getaway! The property was exactly as listed and provided the perfect backdrop for our escape. It was secluded but conveniently located to Keuka Lake, wineries and restaurants! Communication was prompt and helpful. We are already planning a return visit!"
United States
Michael G.
$324 nightly
The price is $362
Sep 30 - Oct 1
Total with taxes and fees
Casita: Near Wineries & Keuka Lake: 100"Projector
A rustic log cabin with a porch, surrounded by trees.

11. Sunny Trails Getaway Cabin

Sunny Trails Getaway Cabin
Cohocton
10.0 out of 10, Exceptional, (18 reviews)
"Really enjoyed our weekend in this cozy cabin."
United States
Jeff D.
$221 nightly
The price is $248
Oct 19 - Oct 20
Total with taxes and fees
Sunny Trails Getaway Cabin
A cozy room with a brown sofa, a blue bed, and a fireplace.

12. Hubbs Cellar at JS Hubbs Guest House

Hubbs Cellar at JS Hubbs Guest House
Hammondsport
10.0 out of 10, Exceptional, (10 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.
$225 nightly
The price is $252
Oct 27 - Oct 28
Total with taxes and fees
Hubbs Cellar at JS Hubbs Guest House
An outdoor seating area with two chairs facing a stone fire pit.

13. Tranquil Airstream Nature Escape

Tranquil Airstream Nature Escape
Bath
9.8 out of 10, Exceptional, (8 reviews)
"Was a wonderful getaway. Cozy and perfect and exactly what we were looking for!"
United States
Melinda L.
$286 nightly
The price is $320
Sep 30 - Oct 1
Total with taxes and fees
Tranquil Airstream Nature Escape
A bedroom with a bed, a nightstand, a bedside table with a lamp, a chair, a wooden floor, and a ceiling fan.

14. Hammondsport Hideaway

Hammondsport Hideaway
Hammondsport
9.8 out of 10, Exceptional, (70 reviews)
"Great location.small but met our needs."
United States
Helen
$227 nightly
The price is $254
Sep 30 - Oct 1
Total with taxes and fees
Hammondsport Hideaway
A log cabin with a snow-covered roof, surrounded by trees.

15. Timber Haven - Serene getaway-Fireplace, air conditioning, fire pit, grill, WiFi

Timber Haven - Serene getaway-Fireplace, air conditioning, fire pit, grill, WiFi
Cohocton
10.0 out of 10, Exceptional, (63 reviews)
"Quiet and secluded cottage, perfect for our weekend family stay!"
United States
Mike F.
$212 nightly
The price is $237
Sep 30 - Oct 1
Total with taxes and fees
Timber Haven - Serene getaway-Fireplace, air conditioning, fire pit, grill, WiFi
A dining room with a table set for four, wooden chairs, a vase with flowers, and a window with curtains.

16. 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, (171 reviews)
"Quiet, clean, and peaceful. We thoroughly enjoyed a chance to relax and enjoy the beauty of Penn-Yan. Mary is a kind and responsive host who contacted me prior to our arrival to ensure all of our needs would be met. We definitely hope to return in the future."
United States
Karen H.
$199 nightly
The price is $223
Sep 30 - Oct 1
Total with taxes and fees
Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake
Private kitchen

17. Lovely 1 Bed Ranch Close to all Attractions

Lovely 1 Bed Ranch Close to all Attractions
Canandaigua NY
4.0 out of 10, (1 review)
"There is NO house number on the building. The host did NOT provide us with info prior to arrival, we had to message him to get access. It appeared that check in was at 4:00, but turned out it was 3:00. The actual property appearance does NOT look like the pictures online. Outside is overgrown, dirty and cobweb’s everywhere. Inside smells musty and gross. Flies everywhere, spiders in the bathroom and shower. It was not clean under the bed. There’s no bathroom soaps or wash clothes and the towels...
United States
Anonymous traveler
$149 nightly
The price is $160
Sep 30 - Oct 1
Total with taxes and fees
Lovely 1 Bed Ranch Close to all Attractions
A dining area with a wooden table, metal railings, and a decorative butterfly wall piece.

18. Junior`s Suite at JS Hubbs Guest House

Junior`s Suite at JS Hubbs Guest House
Hammondsport
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay in this beautiful property!"
United States
Kim C.
$312 nightly
The price is $349
Oct 6 - Oct 7
Total with taxes and fees
Junior`s Suite at JS Hubbs Guest House
A wooden cabin with a sloped roof, a front door, and a covered porch area.

19. 24-acre Finger Lakes Cabin w/ Private Pond

24-acre Finger Lakes Cabin w/ Private Pond
3.0 star property
Arkport
$394 nightly
The price is $441
Oct 18 - Oct 19
Total with taxes and fees
24-acre Finger Lakes Cabin w/ Private Pond
A spacious living area with a kitchen, a sofa, and a dining table.

20. Modern Studio - Main St Penn Yan

Modern Studio - Main St Penn Yan
Penn Yan
9.6 out of 10, Exceptional, (15 reviews)
"Great place downtown over looking Main Street. I really liked the decor and the apartment was fully equiped with everything we needed. Greta coffee place across the street with amazing croissants for breakfast."
United States
Aki S.
$300 nightly
The price is $305
Sep 30 - Oct 1
Total with taxes and fees
Modern Studio - Main St Penn Yan
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 Italy Hotel Reviews

Plum Point Lodge

Plum Point Lodge

8/10 Good
"Beautiful setting on the Lake."
Fran 3-night trip
Posted 2 hours ago
Plum Point Lodge

Find out more about Town of Italy

Discover your perfect Town of Italy vacation rental with Expedia

How many vacation rentals are available in Town of Italy?


Expedia has plenty of vacation rentals to choose from in and around  Town of Italy, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Town of Italy?


The selection of Town of Italy vacation rentals we have selected for you start as low as $169 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Town of Italy?


Vacation rentals in Town of Italy come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Town of Italy vacation rentals to suit everyone. 


Why should I choose a vacation rental in Town of Italy?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Town of Italy vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Town of Italy?


Find vacation rentals in Town of Italy by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Town of Italy.  


What amenities are available in a vacation rental in Town of Italy?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Town of Italy vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Town of Italy?   


Everytime is a great time to head to Town of Italy! Staying in a Town of Italy vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Town of Italy. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Town of Italy vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Town of Italy, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Town of Italy vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.