Photo by My Walkabout

Town of Chili Holiday Rentals

  • Plan, book, stay with confidence

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

Top Holiday Rentals Destinations in Town of Chili

Cozy House with Hot Tub

9.8 out of 10, Exceptional, (33)
"Our stay at this property was absolutely phenomenal. The host was very responsive and the property was immaculate. The wood burning stove, outdoor fire pit on the deck,and the hot tub made this property special. We can't wait to come back and stay again!! I highly recommend staying at this property 5/5!! It is exceptional!!"
The price is AU$510
includes taxes & fees
5 Mar - 6 Mar
Cozy House with Hot Tub

Super Modern 2-Bedroom Riverside Home @ RIT

10.0 out of 10, Exceptional, (5)
"A unique little place with character! As grandparents (who can climb the stairs!) we thoroughly enjoyed our daughter and grandson visiting us throughout the day for hanging out and dinners! Very roomy first level with greatflooring for kids to play. Large kitchen for home cooked meals too! "
The price is AU$269
includes taxes & fees
5 Mar - 6 Mar
Super Modern 2-Bedroom Riverside Home @ RIT

Charming 3-bedroom house in Rochester/UofR & RIT

2.0 star property
9.0 out of 10, Wonderful, (18)
"We had a great trip enjoying the snow! The house itself is old, and definitely needs some repairing, but nothing major that required immediate maintenance. I would say if you go during winter, bring blankets! Theirs are pretty thin. Great backyard! The owners were great and checked in with us throughout the stay. And overall it is what you would expect for the price range, and from the description.It was exactly what we needed for our family trip. No extras, nothing fancy, but great location,...
The price is AU$289
includes taxes & fees
2 Apr - 3 Apr
Charming 3-bedroom house in Rochester/UofR & RIT

Tranquil Retreat on the shores of Lake Ontario

9.4 out of 10, Exceptional, (33)
"The property had so many amenities not found at other VRBOs, the view was amazing, it really made our Thanksgiving special. Would highly recommend. "
Tranquil Retreat on the shores of Lake Ontario

Charming 3-bedroom house in North Winton Village!

9.8 out of 10, Exceptional, (32)
"We loved staying here"
Charming 3-bedroom house in North Winton Village!

Charming 2-bedroom condo with AC and WiFi in Rochester

8.0 out of 10, Very good, (1)
"As noted above, the location and property description were great. There was an issue with the wifi though, which caused too much communication with the owner and manager. We initially were not provided the router name and there were 20 networks available. Second, the password did not work (from any of our 4 devices). At one point in a text string I received "I don't know what to tell you, several other guests have had no problem" - which was not helpful at all. It turned out that the...
Charming 2-bedroom condo with AC and WiFi in Rochester

Newly remodeled home. Walking distance to Seabreeze and to many things around

10.0 out of 10, Exceptional, (11)
"We needed a place to stay while visiting our family over the Christmas Holiday. With family living in Greece and Penfield we were looking for a good in between place to stay that also allowed dogs. Having lived in West Irondequiot before moving to NC I wanted to stay in that area. Jennifer’s place came up and looked like a cozy place to stay. I messaged with Jennifer before booking. She was prompt to respond. The house was clean and well stocked. It was the perfect home away from home. In...
Newly remodeled home. Walking distance to Seabreeze and to many things around

3-Bedroom Private Home with Game Room, Fully Fenced, Near Lake Ontario Shoreline

10.0 out of 10, Exceptional, (1)
"This was a great stay . Really clean and a great location . I will definitely rent again ! "
The price is AU$474
includes taxes & fees
5 Mar - 6 Mar
3-Bedroom Private Home with Game Room, Fully Fenced, Near Lake Ontario Shoreline

Idyllic Rochester Apartment: 2 Miles to Downtown!

8.2 out of 10, Very good, (38)
"We were thankful that we were able to stay at a home that was close to an event my daughter needed to be at. We only had drive about 6 min. I was neverous about parking but it all worked out. If i had any questions or concerns they where great with getting them answered or quick to help in any way. I would recommend this place for a good place to go to events like the strong museum. Most popular grocery's stores where about 15 min. Which i thought was not bad to get to walmart or target. If want...
Idyllic Rochester Apartment: 2 Miles to Downtown!

Gorgeous home walking distance to the beach

9.2 out of 10, Wonderful, (16)
"Great home, wonderful communication. Very nice hosts! We would love to rent from them again!"
The price is AU$521
includes taxes & fees
5 Mar - 6 Mar
Gorgeous home walking distance to the beach

A Cozy, Homely, Fun Retreat minutes from downtown

9.8 out of 10, Exceptional, (11)
"Needed a place to stay when I was in Rochester for a wedding. This apartment was less than 10 minutes from our venue and could accommodate our group of 4 with two very comfortable bedrooms. Each room had its own A/C unit, which was perfect for the heat wave we had over that weekend. We also loved the full kitchen and open living/dining room space. We had plenty of room to prep meals and snacks, as well as work on last-minute wedding projects. Also, loved the screen-in front porch! Wish we had...
The price is AU$320
includes taxes & fees
9 Mar - 10 Mar
A Cozy, Homely, Fun Retreat minutes from downtown

Luxury Rochester Penthouse w/ Unbeatable City View

8.0 out of 10, Very good, (13)
"Stayed here with a few friends and family for my birthday weekend. It was very spacious. Only thing was parking was a bit confusing and we didn’t know how to open the door to balcony so we used the other door. "
The price is AU$462
includes taxes & fees
5 Mar - 6 Mar
Luxury Rochester Penthouse w/ Unbeatable City View

Serenity in South Wedge: desirable walking community meets vibrant tranquillity!

9.8 out of 10, Exceptional, (15)
"This place was in such a perfect location for us to get everywhere we needed quickly, Loved having off street parking. Beds were comfy! Great puzzle table! "
The price is AU$604
includes taxes & fees
14 Mar - 15 Mar
Serenity in South Wedge: desirable walking community meets vibrant tranquillity!

Private luxury apartment in the heart of the city

10.0 out of 10, Exceptional, (32)
"Everything was wonderful and the owner is very kind and welcoming."
The price is AU$395
includes taxes & fees
5 Mar - 6 Mar
Private luxury apartment in the heart of the city

💫Modern & Quiet Suburban Ranch Mins to Dtwn/Stores

10.0 out of 10, Exceptional, (2)
"Communication with the host was prompt and helpful. Very accommodating. Great location. The house was clean, spacious and stocked with essentials. The furnishings were updated and modern. The beds were very comfortable."
💫Modern & Quiet Suburban Ranch Mins to Dtwn/Stores

Village of Fairport - 2 BDRM w/Onsite Parking

9.6 out of 10, Exceptional, (17)
"We needed to stay four days in the area for our son’s college sporting event. This house was perfect for our needs. It was very clean, the communication was great, and it was just as described on the listing. Yes, there are active train tracks nearby, but we knew about it and we didn’t feel that it was disruptive. The location is nice and it is near stores and restaurants. We will definitely book again if we need to be in the area. "
Village of Fairport - 2 BDRM w/Onsite Parking

Family & Friends in Fairport

10.0 out of 10, Exceptional, (103)
"My friends and I were looking for a place to celebrate one of our birthdays. We found our stay to be very pleasant with many amenities and commendations to make us more comfortable. The home was located in a very nice neighborhood a quick ride away from anything you could need. The furniture and decor were quaint and cozy. I would highly recommend for groups who are looking to get away!"
Family & Friends in Fairport

Our Conesus Lake House - Affordable, Quality Vacation Destination

8.8 out of 10, Excellent, (31)
"The house is very cute. The kitchen is well stocked with most equipment you would need. Nice that linens and towels are included. Have to walk past approx10 homes to get down to water and park. Easy location to get to 20A and neighboring lakes."
Our Conesus Lake House - Affordable, Quality Vacation Destination

Large waterfront home at the North End of Conesus Lake with garage game room!

9.4 out of 10, Exceptional, (18)
"We celebrate my Mom's 80th birthday with her children and grandchildren. There was 19 of us and the space was great for what we needed. The game room was great. Everything was neat and clean. "
Large waterfront home at the North End of Conesus Lake with garage game room!

Spacious Rochester Home w/ Heated Pool & Hot Tub!

9.8 out of 10, Exceptional, (24)
"Rented this for my daughter’s wedding party. They were very happy with the place. It was spacious and very clean. Large circular driveway. Location was convenient and close to shopping and restaurants. Ankit the owner, was very responsive to a few questions we have. I would highly recommend for a large group stay."
Spacious Rochester Home w/ Heated Pool & Hot Tub!
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.
Don't see what you're looking for?
See all available properties in Town of Chili
Save an average of 15% on thousands of hotels when you're signed in