Holiday rentals in Webster

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Top-rated holiday rentals in Webster

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Top guest favourite
A bright living space features a comfortable sofa adorned with a yellow pillow, paired with a sleek side table. A wooden dining table with chairs is positioned nearby. Natural light filters through multiple windows, highlighting the tasteful decor and open layout.
Home in Charlotte
4.95 out of 5 average rating, 152 reviews

Victorian Home-2Br/2Ba w/ Huge Porch & Game Room!

I hope your stay leaves you with memories of happy laughter and good times! I hope you always look back on the fond memories, including: Premium Mattresses & Linens for your comfort! Fully equipped kitchen! Games for the kids! Outdoor Furniture and BBQ Grill! In the neighborhood: Abbotts Frozen Custard Windjammers Mr. Dominick's at the Lake Hose 22 Whiskey River Bill Grays Other Attractions: Ontario Beach Ontario Beach Park Antique Dentzel Carousel Charlotte Genesee Lighthouse Charlotte Pier

Top guest favourite
A quaint tiny house is nestled among lush greenery, surrounded by flowering plants and trees. The exterior features a charming white façade with a decorative door and window, accented by climbing vines and colorful blooms, creating a peaceful and inviting outdoor setting.
Tiny home in Cobbs Hill
4.94 out of 5 average rating, 168 reviews

Tiny Tranquility near City Activity

Glamping in a park-like setting! This is a well equipped house with a lofted mattress and an outdoor hot shower. You can explore tiny house country/ city living. Located on private property separate from the residence and is next to a tranquil pet friendly park, walking path and labyrinth. You will be 2min from downtown, Wegmans shopping, Cobbs Hill, which overlooks the city skyline, all Universities and festivals.. Deer, foxes, bunnies, fire flys, unique birds are not garenteed. 😉

Top guest favourite
The exterior of the apartment showcases a two-story structure with gray siding and white trim. A welcoming entrance is highlighted by a dark wooden door framed by large windows. Stone steps lead to the entry, flanked by manicured lawns and black railings.
Flat in Fairport
4.99 out of 5 average rating, 204 reviews

A "Jewel" In The Village

Prepare yourself to relax and enjoy Village Life in this second story apartment! This new 1300 sq. ft. open floor plan apartment is centrally located in the Village of Fairport. Just a short walk to unique Restaurants, Shops and Craft Breweries. Minutes to the Finger Lakes, Wineries, Concert venues and more. The 2nd floor balcony is perfect to end the day. Kick up your feet in front of the fireplace for the night and retire to one of the 2 Charming Master Suites waiting to take you away.

Guest favourite
An open-concept kitchen showcases modern stainless steel appliances, including a refrigerator and oven, complemented by sleek white cabinetry. A spacious kitchen island with seating for three offers a functional dining space. Natural light streams through the windows, highlighting the warm wood flooring.
Flat in Victor
4.95 out of 5 average rating, 264 reviews

Apartment in Victor

Nestled in the heart of Victor, NY this fully renovated apartment is a must stay! Located just north of Canandaigua Lake, south of the city of Rochester and 5 minutes from I-90! This charming apartment includes one full bathroom/laundry room, an open concept kitchen/living area, kitchen island with new stainless appliances and quartz counters. Two bedrooms, primary has a king bed and the second bedroom has two full beds. Apartment is located ABOVE/REAR of the main Victorian home.

Top guest favourite
A charming cottage entrance features a wooden deck leading to a green door with a decorative star. Flourishing green plants and flowers surround the entrance, complemented by a welcoming sign and wall lantern, creating an inviting atmosphere for guests.
Cottage in Ontario
5 out of 5 average rating, 108 reviews

The Lake Nest

If you’re looking for a lovely retreat to hang your hat, unwind and experience a comfortable and tranquil place to watch the sunsets and enjoy a big exhale-The Lake Nest is for you! Minutes from Rochester and close to shops, stores and restaurants -this country cottage is the perfect spot to enjoy beautiful Lake Ontario. Updated with all modern amenities and conveniences, the Lake Nest is the ideal location for boating, fishing, hiking, checking out wineries or visiting lovely parks.

Top guest favourite
Home in Webster
5 out of 5 average rating, 128 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 favourite
A comfortable seating area features a gray couch with decorative pillows, positioned near a stylish wooden coffee table. A staircase with wooden railings ascends in the background, while a plant is visible on the wall, complementing the neutral gray tones.
Bungalow in Rochester
4.95 out of 5 average rating, 170 reviews

Private Getaway! Entire home, 2 Bedrooms

Relax in this home originally built as a summer cottage to escape the city! Seabreeze has that laidback feel to help you unwind and have some fun! Walk to the beach, lighthouse on the pier, restaurants and bars, Seabreeze Amusement Park, bowling, and putt-putt. Miles of trails out the front door! 10 minutes from the city. Dogs welcome! No big property management company. This is my bachelorette pad, run by me! I hope you enjoy your stay as much as I loved living here!

Guest favourite
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
4.85 out of 5 average rating, 181 reviews

Penfield-Webster Home w/Pool - Park Like Setting

Charming 19th century 2,300 sq.ft. farmhouse with 3 large bedrooms on 1 acre. Stately coffer ceiling in expansive living room. Recently update with refinished floors, paint and new kitchen appliances. Inviting breakfast room with french doors leading to side yard. Private 1+ acre yard with 18'x38' in-ground pool on park like setting directly across from Town Park. 5 minutes to shopping and entertainment and a short 15 min. drive to downtown Rochester.

Top guest favourite
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
4.99 out of 5 average rating, 191 reviews

Esten-Wahl Farm - Historic Landmark Victorian Home

The farm is 30 acres of pasture, woods and a stream - peaceful, yet within a bike ride to the village of Fairport and the Erie Canal. There is a small cottage hidden behind the historic barn where we live and care for the animals on the farm. Our guests' privacy is paramount and the farm is yours to wander and enjoy (including the pool and tennis court) as you wish! The pool is open May 15th through September 15th.

Top guest favourite
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
4.95 out of 5 average rating, 171 reviews

Arts & Crafts In-law Suite

This house was built in then1920’s for the doctor that was in charge of Rochester General Hospital. The in-law suite was originally his office and his pharmacy. In the 1950’s the front porch was enclosed to accommodate the receptionist space….. locals can not book

Guest favourite
An open-concept living area features a high ceiling with exposed wooden beams. The modern kitchen is equipped with stainless steel appliances and sleek cabinetry. A comfortable seating area is highlighted by a coffee table and natural light filtering through large windows.
Home in North Winton Village
4.98 out of 5 average rating, 206 reviews

Spectacular Remodeled Home in N Winton Village

House Wilsonia is an 800 square foot tiny home located on a quiet, residential street in the city of Rochester. Conveniently located in the North Winton Village neighborhood, you'll find easy access to expressways, grocery stores, restaurants, bars, and more.

Top guest favourite
A tranquil path winds through lush green grass and trees, leading to a private estate. The driveway is flanked by tall trees, with a spacious building visible in the background, appearing surrounded by nature.
Guest suite in Macedon
5 out of 5 average rating, 147 reviews

Quiet Suburban Apartment

Attached apartment on a large private estate in a country setting with a private entrance and private deck. Close to shopping and golf in Penfield, Webster, Fairport and the Erie Canal. Downtown Rochester is a short 15 minute drive away.

Popular amenities for Webster holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Monroe County
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