Holiday rentals with a pool in Rochester

Charming Pittsford Home-Indoor Pool-4 bedrooms

My home is in the Bushnell's Basin/Perinton part of Pittsford. .5 miles to 490, 4 mi to I-90 and 15 minutes to U of R. Erie Canal is a short walk away. The 17 mi Crescent Trail head is 100 yards away. Fantastic restaurants. The large indoor pool is open year round with new filter and pool heater. A stream is in the fenced backyard. 50 trees provide privacy and shade. The 4 bedrooms are spacious and 21/2 baths ensure no waiting! 2 decks. Golf, Finger Lakes, wineries, & breweries are close.

Family · Location · Air conditioning

NEW Lakeview Escape | Seasonal Hot Tub | Poolside

Stay at Hotel Canandaigua in a modern lake-view condo with a full kitchen, private balcony, high-speed WiFi, pool, seasonal hot tub opening in May, and complimentary docking. * 1 minute to Kershaw Park * 2 minutes to CMAC * 3 minutes to Other Half Brewing * 5 minutes to Canandaigua dining and shops Important: One key fob is provided; guests should coordinate access using the lockbox. The unit has no washer or dryer, but paid laundry is available on the fifth floor for approximately $5 per load

Location · Family · Bathroom

The Parkside House in Geneseo

A classic, 4 BR, Craftsman style Cape Cod, recently updated and centrally located in the historic village of Geneseo, NY with a large backyard, and an above ground pool open seasonally (Memorial Day-Labor Day) Walkable to Main Street, restaurants, shopping, nightlife and SUNY Geneseo's beautiful campus. Situated directly next to Highland Park with access to tennis and basketball courts, sports fields, picnic shelters, walking/fitness trails, playgrounds and an adorable ice rink in the winter.

Value · Location · Accuracy

Life Just Got Better at 12 Corners

This centrally-located home is perfect for a family or a friends get-away! It's conveniently located within walking distance to 12 Corners and minutes to downtown or close to many of our wonderful golf courses. The house is fully equipped for entertaining with a stocked kitchen and great room with double sliding glass doors out to the pool area with lounge chairs, table for eating and a grill. You can enjoy kicking around a ball on the grassy area or sunbathing in the private fenced yard.

Location · Family · Walkability

Country Hideaway

The cottage is part of Hilltop Dog Farm. We operate a state-of-the-art dog boarding facility, and we rescue and foster dogs who are in need of a place to stay. The farm sits on top of a hill overlooking a beautiful pond and wide-open fields. You can wander down on a late sunny afternoon, sit at the dock fishing and enjoy the beautiful sunsets or just hang out at the in-ground pool. You can also meet our residence dogs or check in on our farm mascot Easton, a Micro Scottish Highland bull.

Family · Location · Sleep quality

Historic Finger Lakes Estate | 5BR/5BA | Game Room

Welcome to your private Finger Lakes estate — a beautifully restored historic home designed for unforgettable group getaways. With 5 spacious bedrooms, 5 full bathrooms, multiple gathering areas, and a game room, this property is perfect for wine weekends, wedding groups, family reunions, and celebratory escapes. High ceilings, original hardwood floors and thoughtfully styled interiors create the charm of a classic estate with the comfort today’s travelers expect. **POOL COMING SPRING 2026

Family · Location · Sleep quality

Luxury Home with pool-Historic Strawberry Castle

Treat yourself to this National Historic Landmark situated on 3 acres in the heart of Penfield NY located just 8 miles from downtown Rochester in a safe suburban location. Be our guest at this unique family friendly home perfect for gatherings and making memories. The George Southworth House, affectionately known as the “Strawberry Castle” was built in 1875 and boasts 4 bedrooms and 4 baths. Admire the beauty and craftsmanship of days gone by while enjoying the modern comforts of today

Location · Family · Nearby

4 bed ranch w/pool in Henrietta

Your family will be close to everything when you stay at this centrally-located peaceful residential neighborhood where you can stroll down a trail just across the street and in summer time splash in the above-ground pool while cooking dinner on grill. Fire pit at night with your favorite beverage. Spacious ranch with open floor plan. One master bedroom w/bathroom and 3 other bedrooms, hallway full bathroom , living room, dining area, fully equipped kitchen. Laundry in basement.

Location · Family · Decor

The Green House

Get away from it all when you stay under the stars at this beautiful farm situated on 80 acres of rolling farmland, hills and forests, with horses, chickens and Nigerian Dwarf goats. Walk out the sliding glass door to a fully fenced pool and hot tub overlooking the beautiful rolling hills and woods. We live right next to the Green House. The Famous Finger Lake Wineries and Breweries are a short drive away. We are also 20 minutes away from Bristol Mountain Ski Resort.

Location · Family · Hospitality

Mid-Century Lake House in Finger Lakes Wine Region

This place is a whole vibe! Relax and take in the endless view of Lake Ontario surrounded in Mid-Century Modern style. Create memories in the open concept living, dining & kitchen areas or out on the large deck. Enjoy the large in-ground pool & private hot tub! We also have many indoor & outdoor games. There are multiple seating & dining areas inside & on the lake front. Sleep comfortably on a queen sized mattress in any of the 4 private bedrooms. Have fun!

Family · Location · Kitchen

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.

Family · Location · Air conditioning

Fireplace, theater room, & fully equipped kitchen

Enjoy this newly renovated home nestled in a private cul-de-sac with the town park with playground and walking trails literally in your back yard. Lots to do to have fun—swim in the in-ground pool, make teams for a foosball tournament, gather around the table to play board games, watch a movie in the theater room, or snuggle up by the fire and enjoy a quiet night in. Cook meals in the fully equipped kitchen or on the grill on the back patio.

Family · Location · Pets