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
4.94 out of 5 average rating, 138 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
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, 393 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.

Guest favourite
The bedroom features a spacious white bed adorned with soft linens and decorative pillows. A lighted nightstand is positioned beside the bed, complemented by a framed sign reading 'daydream believer' above the headboard. Soft natural light filters through the curtains, creating a calming atmosphere.
Flat in Highland Park
4.89 out of 5 average rating, 299 reviews

Daydream Believer-Cozy 1bdrm in Swillburg Area

Whatever brings you to Rochester – wish to explore the city, just have a good time, cultural events, sporting events, visiting university, business, or any other reason, the location of the apartment and the way it is suited makes the Daydream Believer your perfect choice! This second-floor walkup apartment is drenched in light, stylish enough to be impressed, yet not too stylish to deter you from unwinding. A lovely space to relax and reset after a busy day whether it is work or play.

Top guest favourite
A spacious living area is characterized by wood beams and polished hardwood floors. A sectional sofa is positioned alongside a large area rug. A dining table with chairs and a modern kitchen area are visible in the background, illuminated by pendant lights.
Loft in Park Meigs
4.91 out of 5 average rating, 252 reviews

Beautiful Historic Loft • King Bed & Work Desk

Stay in this historic Button Factory to experience the best food, business and entertainment in Rochester. From high-end finishes to modern amenities, this loft is the pinnacle of perfection. Here at Lofted Living, we strive for a seamless experience for you, including a dead simple check-in process and periodic check-ins during your stay. With 24/7 availability we will assist you with anything from restaurant suggestions to providing additional towels. Sit back and enjoy your stay!

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, 103 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, 108 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 bright living space features large windows allowing natural light to fill the room. A comfortable sectional sofa with decorative pillows faces a circular coffee table. A wooden desk with a chair is beside a plant, creating a cozy workspace. Two armchairs are positioned opposite the sofa.
Flat in Neighborhood of the Arts
4.98 out of 5 average rating, 442 reviews

Downtown Rochester Retreat - King Bed, Parking

IG @roccitystays TIP: Add us to your wish list; click the ♥ in the top right corner to find us easily • Bright, renovated apartment - quiet, safe street • Neighborhood of the Arts • Steps to Strathallan Hotel and Memorial Art Gallery • Walk to theatre, museums, food & drink, nightlife, shopping • Minutes from airport, 490, colleges • Perfect for business or leisure • Historic details preserved, yet updated with modern conveniences! • AC: Avail May-Oct • EV charger by request

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
4.84 out of 5 average rating, 173 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.

Guest favourite
A well-lit studio features a spacious bed with crisp white linens. Blue curtains frame two windows, allowing natural light to fill the room. A kitchenette with modern appliances and a dining table is visible, along with a wall-mounted television in the background.
Flat in South Marketview Heights
4.94 out of 5 average rating, 253 reviews

Cozy Newly Renovated Studio in Marketview Heights!

Enjoy city living in the South Marketview Heights neighborhood! Walking distance to the Main Street Armory, RBTL's Auditorium Theater, the Rochester Public Market, and many restaurants and local attractions! 10 minute drive to Strong Memorial Hospital, U of R, and Rochester General Hospital. Less than 20 minutes to RIT. Conveniently located 1 mile from Amtrak and Greyhound bus stations. Lots of nearby things to do!

Top guest favourite
A modern studio features an open layout with a spacious kitchen area and a comfortable seating arrangement. Large windows provide natural light and views of Irondequoit Bay. A flat-screen TV is mounted on the wall, and light-colored flooring creates a fresh ambiance.
Flat in Rochester
4.89 out of 5 average rating, 381 reviews

Private sancutary on Irondequoit bay

Stunning private studio nestled on the banks of the prestigious Irondequoit Bay. Enjoy the Peace and tranquility of lake living but the convenience of being so close to downtown Rochester. This property has a gorgeous bay view! Perfect stop over for local events or a weekend getaway. No local guests, property is available to international and out of town traveler’s.

Top guest favourite
A comfortable living area features a large, wall-mounted smart TV above a stylish entertainment console. A soft rug lies under a modern coffee table, with a cozy sectional sofa beside it. Doorways lead to the kitchen and bathroom, enhancing the open feel of the space.
Flat in Corn Hill
4.98 out of 5 average rating, 162 reviews

Historic 1 BR Luxury Apartment

This spacious 1-bedroom apartment is conveniently located in the heart of Rochester. It is fully furnished and includes everything you will need to have a comfortable, enjoyable stay. This is one of three apartments located in a historic multi-unit home (Hosts occupy the main part of the house).

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
4.94 out of 5 average rating, 145 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

Popular amenities for Webster holiday rentals

Quick stats about holiday rentals in Webster

  • Nightly prices starting at

    Webster holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 20 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Webster rentals

  • 5 Average rating

    Webster stays are highly rated by guests – averaging 5 out of 5!

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