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House holiday rentals in Chili Town

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Top-rated house rentals in Chili Town

Guests agree: these houses are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of a two-story house with a light tan façade features bright green shutters and a distinctive round window. A covered porch is adorned with intricate detailing, and lush greenery surrounds the structure, contributing to a welcoming neighborhood aesthetic.
Home in Highland Park
4.96 out of 5 average rating, 395 reviews

Good location, Bright, South Wedge, AC and Parking

We continue to clean fastidiously, and provide excellent ventilation. Spacious 2nd floor flat with skylights, full kitchen and bath, living room, dining room and bedroom. There is Central Air conditioning and off-street parking. We are ideally located in the city of Rochester, close to Highland Park, the U of R and hospitals...and an easy walk to the cafes, (ice cream!) stores, pubs and restaurants of the South Wedge. Downtown in 10 minutes. Roc Cinema also reopened a short walk away.

Top guest favourite
A dining area features a black wooden table surrounded by six chairs. A small plant is placed in a pot beside the table. Light hardwood floors enhance the space, while artwork with green hues adorns the walls. Windows allow natural light to brighten the room.
Home in Pittsford
4.95 out of 5 average rating, 504 reviews

Rochester/Pittsford remodeled contemporary ranch

Great location located in Pittsford and borders Henrietta. Conveniently located to highways and approximately fifteen minutes to downtown, ten minutes to lots of restaurants in Henrietta and lots of shopping. The house has been completely remodeled both outside and in. Restored hardwoods. It has a nice deck that is right off the kitchen. Great spot to sit outside for your morning coffee and wonderful for having dinner outside. About a 10-15 minute drive to RIT and University of Rochester.

Top guest favourite
An open-concept kitchen and dining area is visible, featuring wooden cabinets, stainless steel appliances, and a central island with seating. A natural light source brightens the space, highlighting the blend of modern and rustic elements. A designated workspace with a wooden table is included.
Home in Swillburg
4.93 out of 5 average rating, 141 reviews

Cozy bungalow in desirable area!

Updated 1 bdrm home located right next to South Wedge. Quiet + safe neighborhood with many restaurants, cafes, shops + bars within walking distance. Within ~10 minutes of Highland, Strong, + Rochester General. Enjoy downtown living, while also having the perks of off street parking + an entire house on a dead-end street. Open concept home with eat-in kitchen + dedicated office space – perfect for remote working. Fully fenced in backyard (dogs welcome upon approval). Long or short stays!

Top guest favourite
A comfortable living area features a light grey couch, a dark wood coffee table, and a vibrant green plant. Light from a nearby lamp illuminates the space, while artfully framed pictures adorn the wall, providing a touch of character. An archway leads to a dining area visible in the background.
Home in Upper Monroe
4.93 out of 5 average rating, 639 reviews

Spacious 2 Bedroom in Vintage 1910 Southeast Home

Enjoy a spacious, private apartment in an old home nestled in a quiet corner of Southeast Rochester with culture and nightlife nearby. Located in Swillburg, it is near the city center, U of R, and Rochester’s many museums, universities, and restaurants. Inside, relish in the memory foam beds, renovated full kitchen, claw foot tub, comfortable furnishings, and blazing fast Wi-Fi. And, with the owner living on site, it’s like having a friendly neighbor upstairs. You’ll always feel safe.

Guest favourite
A well-lit bedroom features a spacious bed dressed in white linens, accompanied by a pale yellow accent pillow. Two windows with light yellow curtains allow natural light to brighten the room. A small bedside table with a lamp and a decorative area rug are also present.
Home in Rochester
4.94 out of 5 average rating, 298 reviews

3 bedroom ranch, near U of R and RIT, Fast WiFi!

Welcome to this newly remodeled 3 bedroom / 2 bathroom ranch! Conveniently located just 10 miles from downtown Rochester and 7 miles from the Greater Rochester Airport. Easy access to I-390 and I-90 and close to a variety of dining, shopping, and entertainment options. Enjoy modern finishes, keyless entry, and high-speed fiber optic Wi-Fi to keep you connected. Whether you're visiting local colleges or enjoying Rochester's many attractions, this is the perfect home base for your stay!

Top guest favourite
Home in Webster
5 out of 5 average rating, 111 reviews

Amazing 2 bdrm home Fantastic area, close to city.

Relax and unwind in this beautifully updated 2 bedroom home conveniently located just 8.5 miles from Downtown Rochester in the town of Penfield bordering the the town of Webster- “Where Life is Worth Living”. You will love the location with shopping, movies, entertainment, and of course, lots of restaurants all very close by. A hop, skip and jump away from beautiful Irondequoit Bay, take this opportunity to rent boats, kayaks and paddle boards and enjoy all the area has to offer.

Top guest favourite
A spacious living area features a large, tan sectional sofa adorned with decorative pillows. Natural light filters in through two skylights, illuminating the open space. A dining table is visible in the background, creating an inviting atmosphere for gathering.
Home in Pittsford
4.96 out of 5 average rating, 169 reviews

Beautifully renovated-private residence in Pittsford with 3 acres.

Forget your worries in this spacious and serene space. This is a gorgeous house set on 3 acres in Pittsford with close proximity to restaurants, shopping, and easily accessible to highways. This house can sleep up to 10 people. It would make an ideal house for a family gathering or could simply be a great retreat for a couple. There are many possibilities-not limited to just a typical Airbnb. You could easily host bridal/baby showers and parties that could accommodate many people.

Guest favourite
An open living room features a plush gray sofa with decorative cushions, positioned beside a dark coffee table. Natural light flows through a window, highlighting the rich hardwood floors and classic gumwood trim. A dining area is visible in the background, complemented by a stylish painting.
Home in North Winton Village
4.92 out of 5 average rating, 104 reviews

Artists’ House in North Winton Village/ No Fees

Coming to visit family or for work? Centrally located house with the charm of the 1930s and the comforts of today. Beautiful hardwood floors and original gumwood trim. New queen-sized beds, linens, TVs, and appliances. This location is amazing. Plenty of space to get work done or just relax. High-speed fiber-optic internet. There is a washer and dryer available with detergent and fabric softener. Lots of original photography and art throughout the house. Off-street parking.

Top guest favourite
A light-colored, two-story house is shown with a sloped roof and multiple windows. A small deck with chairs is located at the entrance. Surrounding greenery includes trees and grass, providing a natural setting.
Home in Scottsville
4.98 out of 5 average rating, 207 reviews

The Baus Haus

We are surrounded by farmland, a great base for family vacations. There is a grocery store, drug store, antique shops, and family restaurants 5 minutes in either direction from the house. Located 20 minutes from downtown Rochester, RIT, and the University of Rochester, and 1 hour from Niagara Falls, the LeRoy exit to the NY State Thruway is 10 minutes away. We are 30 minutes from Conesus Lake and the entrance to the other Finger Lakes.

Top guest favourite
The exterior of a two-story red cottage is visible, set in a green landscape. Lush foliage surrounds the entrance, and a walkway leads to the front door, which features a window. Mature trees provide natural shade and enhance the charming rural setting.
Home in Churchville
4.98 out of 5 average rating, 159 reviews

Guest home in Churchville

Relax and unwind or take in all the sights Western NY has to offer from the comfort of this family friendly 2 bedroom cottage. Located 3 miles from downtown Churchville, you'll be surrounded by farm fields and trees in this peaceful country space. The patio is a great place for outdoor dining, sitting with your morning coffee, or enjoy a camp fire. Our Kitchen is fully equipped to accommodate your cooking needs.

Top guest favourite
A modern living area features a wall-mounted television displaying a scenic view. Below, an electric fireplace adds warmth. A comfortable sofa and a glass coffee table are arranged with a foosball table nearby. A dining area with dark chairs sits in the background under bright lighting.
Home in Rochester
4.97 out of 5 average rating, 129 reviews

Henrietta NY Escape: Sauna & Spa Garden

⚠️Please read the full description and view all photos before making a booking. Thank you! SAUNA 🧖‍♀️ Sauna pass: $36 👫 1 Sauna Pass pays for everyone 💳 QR code posted inside for payment 🎟️ 1 Sauna Pass = one day unlimited use 🔑 To access room only for entire stay, 1 Sauna Pass required 🚨Book the sauna before or on check-in day covers access for check-in day and the next day. Extra days are $36 each

Top guest favourite
The exterior of a renovated 1800s schoolhouse is showcased, featuring a striking red facade and white trim. A bell tower is positioned above the entrance. The surrounding landscape is blanketed in light snowfall, complementing the serene rural setting.
Home in Canandaigua
4.96 out of 5 average rating, 103 reviews

Renovated 1800s Schoolhouse with 2 bedrooms

Make history a part of your vacation in this renovated 1800s schoolhouse. This historic house is located in the heart of the Finger Lakes. Built in 1886 and in service as a one room school until 1952, this home is truly a special place. Whether you are visiting from afar or looking to unwind on a peaceful staycation, this private two-acre space is your cozy home away from home.

Popular amenities for house rentals in Chili Town

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Quick stats about house rentals in Chili Town

  • Total holiday rentals

    Explore 40 holiday rentals in Chili Town

  • Nightly prices starting at

    Chili Town holiday rentals start at £23 per night before taxes and fees

  • Verified guest reviews

    Over 2,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Chili Town holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chili Town rentals

  • 4.7 Average rating

    Chili Town stays receive an average rating of 4.7 out of 5 from guests

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