Holiday rentals with breakfast in Monroe County

Historic Craftsman Bungalow

4 West Brook Road is a craftsman bungalow in the heart of Pittsford, New York. I love to share my primary residence with other world travelers who enjoy unique experiences and world class architecture. The bungalow is nestled in a park like setting only minutes from local amenities: grocery and liquor stores, restaurants and theaters. This home is an original Sears Roebuck Kit House which is listed on the National Registry of Historic Homes, and is beautifully restored with period furnishings.

Location · Value · Comfort

Silo Glamping Getaway

Get away from the rush and noise of everyday life for a pintrest-worthy stay in our silo bed and breakfast! Build a campfire and relax in the Adirondack chairs or flip on the propane fire on the deck and enjoy a cup of coffee! You might even catch our resident bunny family hopping around the hilltop or a few deer wander through. Wake up to a gorgeous sunrise right outside your door! ***now that school is starting up, pricing reflects breakfast no longer being served...check out the local diner!

Value · Family · Comfort

Perfect house and location

This special place is close to everything, making it easy to plan your visit. A charming and unique property located in the heart of Pittsford village. The main living area is spacious and open, offering a perfect space for entertaining guests or relaxing with family. Upstairs you’ll find 3 well appointed bedrooms, offering plenty of closet space and natural light & a full bathroom. The master suite also features a full bathroom. Don’t miss your opportunity to rent this one of a kind property!

Location · Walkability · Hospitality

Near UR & RIT • Parking • Walkable Corn Hill

Perfectly located for University of Rochester and RIT visits, graduation weekends, and downtown Rochester. Just 5 minutes from UR and the city center, this upscale Corn Hill apartment offers a stylish stay with free dedicated parking. In the heart of historic Corn Hill, enjoy walkable access to restaurants, coffee shops, museums, and the Genesee Riverway Trail. Ideal for business, medical, or campus visits—experience the best of Rochester right at your doorstep. Ask about extended stay rates.

Value · Family · Parking

COZY TINY CITY HOUSE, A BEAUTIFUL HIDDEN GEM.

This Tiny House is a city's hidden gem. Nestled in a diversity cultured neighborhood ..a beautiful relaxing hide-away. Cozy bedroom studio that sleeps 1-2 people. Centrally located on a one way street providing a 5 min drive to Downtown and the city's everything beautiful, business & entertaining. Rich with social opportunities. Secluded behind the gated main home, with private entrance, parking, outdoor patio, and BBQ grill. Here's a certain Suburbanization within the Urban life.

Value · Location · Indoor spaces

Entire guest floor w/kitchenette. No cleaning fee

Relish a peaceful stay on the charming, private 3rd floor within our century-old home. Enjoy simple comfort with lots of little extras that guests praise! / Please read full listing/ Next to a park and 12min to downtown or Lake Ontario! There's space to work or relax, 2 TVs, 2 comfy beds, and a light-duty kitchenette stocked with quick breakfast items, snacks, coffee & teas. Next to a park. Near hospitals. 15min to airport, 18 to RIT. We love hosting, and our stellar guest-rating shows it!

Value · Family · Getting around

2 bedroom, near 490/590/city

Home away from home is comfortably decorated and works well for groups up to 6 people. Three queen beds in the unit. It has a full kitchen with nice spaces for dining inside or out. The neighborhood has a sidewalk with parks nearby. It is strategically located equidistant to both the 590 and 490 entrances by less than 3 miles each way. The east side towns are also all within about 3 miles. Excellent grocery stores and restaurants are very close by. Parking for 1 vehicle on property.

Value · Family · Bathroom

Cute room in the RIT / U of R / and Airport area

Cute small upstairs private room less than a mile from RIT and about 4 miles from U of R. You will share the entire house with just the owner, enjoying the tranquility of the Black Creek area. You can walk to the boat launch area just a few steps from the house at the junction of the Genesee river and the Black creek. This really is a unique place if you need a quiet, peaceful and relaxing place for the night. It's like countryside living, far from the city, and yet, close to everything.

Value · Location · Shared spaces

Fairport Village Original Airbnb

Quaint studio apartment in a unique 4-unit property that is all about location! Right in the Village of Fairport and across the street from locals' favorite breweries & distillery. -Walkable to Erie Canal path, shops, and several bar & restaurant options. -16 minute to Downtown Rochester -10 mins to St. John Fisher & Nazareth College Small and simple is the name of this studio while providing all the essentials for your stay. *Note we are professionally cleaned and sanitized*

Family · Value · Condition

Cozy Getaway by the Bay.

STR or MTR welcome ! Spacious and serene space. Perfect for medical professionals traveling nurses or work remote lifestyle. Well stocked kitchen with breakfast bar and dining table. Tucked in the woods with views of the Bay, but close to the highway, Rochester Regional, URMC, Lake Ontario and downtown Rochester. 10 minutes from all Rochester has to offer. Plenty of off street parking. Walking trails, restaurants & more. Longer stays available January - April. Inquire for rates.

Location · Family · Indoor spaces

Private & Zen 3rd floor studio, near hospitals

Enjoy this fully renovated, private 3rd floor zen space, near Strong & Highland Hospitals, R.I.T. and the airport. Intuitively and artistically designed with comfort, convenience and relaxation in mind. Light-duty custom kitchenette. Private bath with over-sized, custom-tiled, walk-in shower. Dedicated workspace with large desk and Wi-Fi. Queen bed with deep memory foam mattress. 42" flat screen Roku smart tv. Lots of extras. Unwind and relax! ** Weekly Discounts Available **

Family · Location · Getting around

Paradise East (Golfing & Gatherings!)

This Pittsford home is centrally located. It's a short stroll to Oak Hill Country Club, a brief trip to Wegmans, Trader Joe's and Whole Foods, and a short, scenic drive to Canandaigua Lake. Paradise East has five bedrooms with option to set up an additional queen bed & twin. Each bedroom has been curated with handcrafted, artisan furniture. We leave the Victorian era for modern bathrooms, a serious chef kitchen and a spacious patios with spectacular east and north views.

Family · Value · Condition