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House vacation rentals in Chili Town

Find and book unique houses on Airbnb

Top-rated house rentals in Chili Town

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

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Guest favorite
Home in 19th Ward
4.94 out of 5 average rating, 471 reviews

Kiwi Cottage - country space, timeless city charm

Special rates Jan, Feb 7-30 days. Send msg. Comfortable, charming, fully equipped home. Walk to UofR, CollegeTown, Strong Hospital. RIT 6 minute drive. Free parking on property. Renovated period home (wood floors may squeak!) currently 1 1/2 bathrooms (back to 2 full by mid Jan 26), well stocked kitchen, deck & huge backyard w/many, wildlife! Guests like cleanliness, comfortable beds, full range of amenities. Central a/c, washer, dryer. Sleeps 6, couch for 7th. Keypad entry, fast WiFi.

Guest favorite
Home in Canandaigua
4.92 out of 5 average rating, 274 reviews

Bristol Retreat Cottage

Unwind at this romantic getaway nestled in the beautiful Bristol Hills, just minutes away from Bristol Ski Resort, Canandaigua and Honeoye Lakes. This unique 1 bedroom 1 bathroom cottage is one of our two homes on the property along the peacefully flowing Mill Creek. Take in the natural beauty from the large patio and hot tub. Inside, enjoy the warmth of the gas fireplace, complimentary wifi and smartTV. The full kitchen and bathroom are well stocked with amenities to ensure a comfortable stay.

Top guest favorite
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, 399 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.

Superhost
The exterior of a two-story home is showcased, featuring a wooden deck with seating and a hot tub. A well-maintained garden surrounds the property, adorned with vibrant flowers and stone pathways, creating a serene and inviting outdoor space.
Home in Rochester
4.95 out of 5 average rating, 254 reviews

Cheerful Garden Oasis/ Hottub + Christmas Decor

Cheerful Garden Oasis! A peaceful and scenic 2 story home close to everything Rochester has to offer. A luxury listing where you will enjoy the historic and beautiful neighborhood of Brighton. Warm up by the gas fireplace in winter. Bike to Brickyard Trail or Twelve Corners for ice cream in summer. Relax on the patio or in the hottub with views of beautiful gardens as ambient uplighting turns on at night. Sit by the firepit and make smores! Keep your eye out for wildlife and deer spotting.

Top guest favorite
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, 142 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 favorite
An open-concept living area is revealed, featuring comfortable seating arranged around a coffee table. A large TV is mounted on the wall opposite plush armchairs. Natural light filters through multiple windows, illuminating the modern kitchen and dining space.
Home in Pittsford
4.99 out of 5 average rating, 112 reviews

Elegant Farmhouse in Pittsford (near Rochester)

Newly renovated house in heart of Pittsford. 3 Bdrms & sofa bed ! Each bdrm has full bath, TV & Ceiling fan. 1st flr laundry & 1/2 bath. WiFi. New appliances. Long driveway with parking for 6 cars, RV or even 18 wheeler! Bottled water, Reg/Decaf Coffee & Tea provided. Walk/Bike trail across street. 5min drive to Pittsford village, Bushnell’s Basin, East View Mall, Colleges (Nazareth and St. John Fisher), Golf courses, Wegmans Grocery store, shopping plaza’s and restaurants.

Top guest favorite
Home in Webster
5 out of 5 average rating, 113 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.

Guest favorite
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, 171 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.

Top guest favorite
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, 208 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 favorite
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, 162 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 favorite
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
4.95 out of 5 average rating, 132 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 favorite
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, 104 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 Chili Town house rentals

When is the best time to visit Chili Town?

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Avg. priceﺩ.ﺇ463ﺩ.ﺇ437ﺩ.ﺇ470ﺩ.ﺇ470ﺩ.ﺇ514ﺩ.ﺇ525ﺩ.ﺇ551ﺩ.ﺇ555ﺩ.ﺇ488ﺩ.ﺇ518ﺩ.ﺇ536ﺩ.ﺇ507
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Quick stats about house rentals in Chili Town

  • Total vacation rentals

    Explore 40 vacation rentals in Chili Town

  • Nightly prices starting at

    Chili Town vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 2,040 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Chili Town vacation rentals include wi-fi 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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