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Family-friendly vacation rentals in Chili

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Chili

  • Total vacation rentals

    Explore 30 vacation rentals in Chili

  • Nightly prices starting at

    Chili vacation rentals start at G$12,549 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,890 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Chili vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chili rentals

  • 4.8 Average rating

    Chili stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Chili

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
Home in Rochester

Kiwi Cottage - country space, timeless city charm

Center city 3 bed/two bath, huge backyard, walk to UofR, Strong Hospital, Genesee River Park playground, city trail network, 6 min RIT, 10 mins restaurants, key attractions. Ample offstreet free parking. Frequent guest comments: Lovely house! Clean! Charming! Renovated period home, 2 full bathrooms, walk-in showers (no bathtub). Fully equipped kitchen. Coffee, tea, pantry items. Watch wildlife from a deck lounger. Central a/c, washer, dryer. Sleeps 6, couch for 7th. Keypad entry, fast WiFi.

FamilyIndoor spacesAccess

4.94 out of 5 average rating, 502 reviews
Top guest favorite
A spacious dining area is highlighted by a dark wood table surrounded by black chairs. Soft lighting from a pendant fixture enhances the warm tones of the cabinetry and decor. A runner decorates the table, with a vase of pale flowers serving as a focal point.
Home in Rochester

Spacious Suburban Home in Gates NY

Cozy Home Away from Home in Gates, NY! Nestled in a quiet, family-friendly neighborhood, our cozy home is just 8 minutes from downtown Rochester, minutes from the airport, a local movie theater, and the iconic Wegmans grocery store—making it a convenient and comfortable home base for your stay. Whether you’re visiting family, exploring the Finger Lakes region, or traveling for work, you'll appreciate the fully equipped kitchen, spacious living areas, and a private backyard perfect for relaxing!

Indoor spacesFamilyCleanliness

4.94 out of 5 average rating, 102 reviews
Top guest favorite
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

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.

KitchenIndoor spacesAccess

4.95 out of 5 average rating, 560 reviews
Top guest favorite
Apartment in West Henrietta

Perfect "Home away from Home" Near RIT and U of R

Perfect "Home away from Home" with lots of natural light. Spacious and delightful, first floor apartment is only 2 miles from RIT (Rochester Institute of Technology) and 5 miles from U of R. Only 6 miles from Roc Airport. Very Safe, quiet neighborhood with sidewalks, and private ponds for fishing or kayaking. Free parking for 1 car. Enjoy gas fireplace, central heat, central air, and Wifi. Ready to use kitchen, coffee maker, Beautiful porch with patio furniture, Gas/charcoal grill.

KitchenIndoor spacesCleanliness

4.99 out of 5 average rating, 300 reviews
Top guest favorite
Guest suite in Rochester

Private suite on Genesee River near RIT

Enjoy views of gardens and the Genesee River. Walk to RIT, drive or Uber to shop or dine nearby. Suite has a private entrance and is equipped with a microwave, toaster oven and conduction burner, coffee maker, WiFi and TV. Nicely private and comfortable. For any two guests needing separate sleeping arrangements there is a chair-lounger-bed (twin size) available with provided bedding. NOTE: The bathroom has a sloped ceiling, as pictured. if you are very tall, it may be uncomfortable.

FamilyKitchenWalkability

4.88 out of 5 average rating, 234 reviews
Top 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

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.

KitchenIndoor spacesNearby

4.96 out of 5 average rating, 213 reviews
Top guest favorite
The exterior of a charming brick schoolhouse is showcased in the soft glow of evening light. Lush greenery surrounds the building, while flower beds are neatly arranged in front. The entrance is framed by warm wall sconces, welcoming guests into the historic structure.
Place to stay in Churchville

Wheatland Schoolhouse No.7

Step into history with modern comfort at our beautifully renovated 1800s schoolhouse. Features a king bed in the loft, queen bed on the main floor, and two full baths on each floor. Relax in the spacious living area or cook in the fully equipped kitchen. Perfect for families, couples, or friends seeking a peaceful country escape just minutes from Rochester. Every booking helps fund the continued care and preservation of this historic schoolhouse so its story can live on.

KitchenIndoor spacesComfort

5.0 out of 5 average rating, 109 reviews
Top guest favorite
A spacious wooden deck is framed by greenery, featuring multiple seating areas. The design includes built-in benches and an inviting layout, creating an ideal space for relaxation and outdoor enjoyment.
Guest suite in Rochester

Private ,furnished ,modern Roch suburb apt !

First this is a private apt. It is not shared with anyone ! A beautiful little cozy spot with a kitchen with all the ammedities . Skylights make this place a bright cheerful place no matter what the season. Washer and dryer with a large walk in closet .A train goes through about a mile away a few times a day. You can hear it from a distance. I myself don't even notice it, but wanted to note it . WE DO NOT BOOK TO LOCALS! You must speak with me first unless approved.

KitchenFamilyHiking

4.94 out of 5 average rating, 393 reviews
Top guest favorite
A private rectangular pool is surrounded by a sleek gray concrete patio and secured with a black metal fence. A water slide curves into the pool, while lounge chairs are arranged nearby. Lush green trees provide a natural backdrop.
Home in Bloomfield

2 Bedroom pool house with Garage

Make some memories at this unique and family-friendly place. Peaceful location that is close to Rochester and Canandaigua as well as Bristol Mountain for skiing or viewing foliage. Tranquility at your fingertips. The pool is generally open from Memorial weekend until Labor day weekend. The last day the pool will be heated for 2025 is September 27th. The pool is shared with the resident of the main home which is a family of 5 with 5 kids aged 1 to 10.

Indoor spacesKitchenSleep quality

4.99 out of 5 average rating, 137 reviews
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

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.

KitchenIndoor spacesNearby

4.98 out of 5 average rating, 218 reviews
Guest favorite
A red wooden staircase leads up to a private entrance on the side of the apartment. The entrance is framed by light-colored siding and a modest outdoor light. Lush greenery and grass surround the walkway, contributing to a serene outdoor setting.
Guest suite in Rochester

Completely furnished 1 bdrm in suburbs!

Relax in this cozy, fully furnished in-law apartment with a private entrance, thoughtfully separated from the main home by a hallway and two doors for added privacy. Nestled in a quiet suburban neighborhood, yet just minutes from expressways, shopping, restaurants, and local colleges. Greater Rochester Airport is only 15 minutes away, and Roberts Wesleyan College is just 2 minutes. Shared driveway with plenty of parking.

Indoor spacesFamilyValue

4.93 out of 5 average rating, 200 reviews
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

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.

Indoor spacesFamilyParks

4.99 out of 5 average rating, 201 reviews

Popular amenities for Chili family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A comfortable seating area is presented with a dark blue sofa adorned with decorative pillows. A matching loveseat is positioned nearby, creating a cozy atmosphere. A patterned area rug lies under a simple coffee table, adding a touch of color to the space.
Home in Brighton

Suburban Cabana

Indoor spacesFamilyOutdoor spaces

4.82 out of 5 average rating, 165 reviews
Top guest favorite
A spacious living area is highlighted by a large sectional couch and a contemporary dining table. Natural light filters through multiple windows, while a striking black-and-white artwork adorns the wall, contributing to the room's modern aesthetic.
Home in Pittsford

The Retreat in Pittsford / amazing yard W Hot Tub

FamilyIndoor spacesGrill

5.0 out of 5 average rating, 114 reviews
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 Brighton

Cheerful Garden Oasis/ Hottub + Holiday Decor

FamilyKitchenGrill

4.93 out of 5 average rating, 303 reviews
Top guest favorite
A modern dining area is presented with a rectangular glass table surrounded by six dark wooden chairs. A light fixture hangs above the table, illuminating the space. Large windows allow natural light to enter, complemented by white curtains and decorative plants in the corner.
Home in Rochester

Spacious Park Ave Retreat w/ Hot Tub and AC!

Indoor spacesFamilyNearby

5.0 out of 5 average rating, 114 reviews
Guest favorite
A one-story cottage is set near Lake Ontario, framed by lush greenery. Wooden decking leads to the entrance, while a grassy area extends towards the water's edge. The structure features large windows and a simple exterior. A vehicle is parked nearby, highlighting the accessible location.
Home in Kendall

The Love Shack

FamilyKitchenParking

4.78 out of 5 average rating, 120 reviews
Top guest favorite
A spacious living area features a natural stone fireplace, surrounded by comfortable seating including a dark blue armchair and a light grey sofa. Large windows bring in natural light, and artwork adorns the wooden walls, enhancing the cabin's inviting ambiance.
Home in Canandaigua

Finger Lakes Hilltop Chalet Relax, Unwind & Renew

Indoor spacesFamilyQuiet

5.0 out of 5 average rating, 116 reviews
Superhost
Home in Canandaigua

Bristol Hills Cabin

Indoor spacesKitchenCheckout

4.91 out of 5 average rating, 251 reviews
Top guest favorite
The cabin exterior features a metal roof and a spacious deck with railing, surrounded by trees. A grill is positioned on the deck, and outdoor seating is available. The serene landscape showcases a glimpse of Canandaigua Lake in the background.
Guesthouse in Naples

Grandpa-T’s Guest Cottage at Hawks Landing

KitchenFamilyGetting around

4.98 out of 5 average rating, 298 reviews

Family- and pet-friendly home rentals

Guest favorite
A spacious living area features a comfortable, oversized sofa adorned with decorative pillows and a cozy throw. A glass-top coffee table sits in the center. Natural light pours in through two large windows, enhancing the warm ambiance of the room.
Home in Henrietta

Cheerful Henrietta 4BDRM. w/Garage - Pets welcome!

FamilyKitchenCheck-in

4.81 out of 5 average rating, 129 reviews
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

Elegant Farmhouse in Pittsford (near Rochester)

Indoor spacesFamilyLayout

4.98 out of 5 average rating, 161 reviews
Guest favorite
A spacious three-bedroom home is showcased, featuring a light-colored exterior with two prominent entrances. The well-maintained lawn is bordered by trees, providing a natural setting. A paved driveway is visible, offering ample parking space. Red chairs are positioned invitingly on the porch.
Home in Brockport

Brockport's Home away from Home!

Indoor spacesKitchenGrill

4.92 out of 5 average rating, 158 reviews
Guest favorite
A comfortable living space features a cozy sofa and stylish armchair arranged around a low coffee table. A flat-screen television is mounted above a brick fireplace, with natural light filtering through the windows. Greenery is placed near the fireplace and on the coffee table.
Apartment in Rochester

Gem on Genesee Park

FamilyKitchenAmenities

4.91 out of 5 average rating, 193 reviews
Guest favorite
A spacious living area features a comfortable sectional sofa and a coffee table, with cozy accent chairs nearby. Soft lighting from multiple sources enhances the atmosphere. Artwork hangs on the walls, complementing the natural light streaming in through the windows.
Home in Rochester

The Roc-House 4Bd, 2BA, Near Airport, Home Office

FamilyKitchenAccess

4.82 out of 5 average rating, 148 reviews
Guest favorite
The exterior of a two-story house showcases a combination of brick and blue siding with architectural detailing. A wide front porch with stone pillars is accented by a manicured lawn and pathway, leading to the entrance. The surrounding trees enhance the outdoor setting.
Guest suite in Rochester

Arts & Crafts In-law Suite

KitchenFamilyBathroom

4.94 out of 5 average rating, 213 reviews
Guest favorite
An aerial view of a three-story lake house bordered by a lush green lawn. A private dock extends into the water, while a row of tall trees provides a natural backdrop. Nearby, a gravel path leads to a road lined with greenery.
Cottage in Livonia

Hayes Hideaway, The Perfect Lakeside Getaway

Indoor spacesKitchenPool

4.83 out of 5 average rating, 125 reviews
Guest favorite
The entrance to the cabin is framed by a warm-toned wood exterior, featuring a prominent 'Welcome' sign. A green door leads into the home, while a wooden ramp provides accessibility. Various sized stones decorate the landscape around the porch.
Cabin in Bloomfield

Relaxing Getaway Cabin...Explore The Finger Lakes!

KitchenIndoor spacesView

4.93 out of 5 average rating, 334 reviews

Family-friendly home rentals with a pool

Top guest favorite
A welcoming seating area is presented with two soft blue armchairs positioned on a decorative rug featuring floral patterns in shades of blue and cream. A small table with a lamp is situated between the chairs, and natural light enters through a large window overlooking a grill area.
Home in Pittsford

Charming Pittsford Home-Indoor Pool-4 bedrooms

FamilyKitchenValue

4.89 out of 5 average rating, 148 reviews
Guest favorite
The exterior of a two-story white house is framed by lush green trees and manicured lawns. The front porch features white railings, while large windows reflect the sunlight, enhancing the inviting appearance of the home. A sense of spaciousness is conveyed by the surrounding open area.
Home in Fairport

Esten-Wahl Farm - Historic Landmark Victorian Home

KitchenFamilyCleanliness

4.97 out of 5 average rating, 204 reviews
Top guest favorite
The living room features two comfortable leather sofas positioned across from each other, centered around a circular coffee table. A gas fireplace with a stone surround is visible, complemented by a wall-mounted TV above it. Natural light fills the space through large windows.
Home in Lima

Fireplace, theater room, & fully equipped kitchen

FamilyKitchenPets

4.96 out of 5 average rating, 210 reviews
Guest favorite
The yellow farmhouse is set amidst lush greenery, surrounded by trees. A spacious driveway leads to the front porch, which is shaded by overhanging branches. A basketball hoop and a grill are visible near the garage, contributing to the outdoor recreational space.
Home in Penfield

Penfield-Webster Home w/Pool - Park Like Setting

Indoor spacesFamilyCheck-in

4.84 out of 5 average rating, 191 reviews
Top guest favorite
A vast, open landscape features rolling hills and fields of green, under a clear blue sky. Sparse trees line the edges of the property, with a distant view of a white farm structure nestled among the greenery.
Barn in Bloomfield

The Green House

Indoor spacesKitchenHot tub

4.97 out of 5 average rating, 115 reviews
Top guest favorite
A serene outdoor space features a fenced-in in-ground pool surrounded by lush greenery and trees. A striking double rainbow arches across the sky above a rustic building, enhancing the natural charm of the setting.
Home in Marion

Spacious Updated Country Home

Indoor spacesKitchenDecor

5.0 out of 5 average rating, 106 reviews
Top guest favorite
A group of five cows is seen grazing in a lush green pasture. The cows exhibit a mix of colors, including black, white, and brown. In the background, trees and rolling hills create a serene rural landscape.
Camper/RV in Scottsville

Happy Camper Scottsville

Indoor spacesKitchenAccuracy

4.98 out of 5 average rating, 85 reviews
Top guest favorite
Home in Penfield

Luxury Home with pool-Historic Strawberry Castle

KitchenIndoor spacesDecor

5.0 out of 5 average rating, 48 reviews

When is the best time to visit Chili?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$28,653 GYDG$29,281 GYDG$31,999 GYDG$33,254 GYDG$35,346 GYDG$35,137 GYDG$32,836 GYDG$33,254 GYDG$31,372 GYDG$31,372 GYDG$31,790 GYDG$31,372 GYD
Avg. temp-3°C-3°C2°C8°C15°C20°C22°C22°C18°C11°C5°C0°C

Destinations to explore