Family-friendly holiday rentals in Jamestown

A cozy living room is presented with soft, natural light filtering through two windows. A striped sofa offers comfortable seating, complemented by two armchairs. A round wooden coffee table sits at the center on a plush area rug, creating an inviting gathering space.

4.94 out of 5 average rating, 144 reviews

Quaint 2 bedroom home overlooking bird sanctuary

2 bedroom house in a quiet neighborhood. just a minute from exit 12 off of I86 , Keybox self checkin arrive as late as you need to.. Beds and bathroom up on the second floor, and it's an old house, stairs are steep.. kitchen, dining and living room on first. Enclosed front porch great for morning coffee, walk out basement has laundry, a flop futon and secure bike storage. Yard overlooks RTPI bird sanctuary and has outdoor seating area with firepit. Driveway parking. Host in neighborhood ,

4.97 out of 5 average rating, 106 reviews

A spacious living area features a comfortable gray sofa with decorative pillows, positioned on a polished floor. A stylish area rug lies beneath, and a modern ceiling fan enhances airflow. A staircase leads to the loft bedroom, while the kitchen and dining area are visible in the background.

Barn in Jamestown

Barndominium 132

Welcome to your mini vacation or getaway in this modern, newly constructed apartment! This cozy & stylish space is perfect for up to four people, with 2 bedrooms one being on the 1st floor each featuring a queen bed, ensuring a good nights sleep for everyone. The apartment also features a modern kitchen w/ all the amenities, WIFI & TV's included, you will never miss your favorite shows or miss an email. Off street parking, private patio, bath & laundry conveniently on the main floor.

A wooden back deck provides seating options, including a glass-topped table and several chairs, with ample space for relaxation. Surrounding greenery and trees offer shade, while a view of the lake is visible in the background, completing the serene outdoor atmosphere.

4.85 out of 5 average rating, 122 reviews

Charming West Ellicott Cottage with Lake View

Nicely decorated with lake theme. Minutes from Lakewood, the Chautauqua Harbor Hotel, Bemus Point and Downtown Jamestown. New kitchen in June 2025. Back deck with spectacular lake views, and campfires in the back yard. National Comedy Center - 3 miles Southern Tier Brewery - 4.2 miles Ellicottville Brewing - 11 miles Lucille Ball House - .25 miles Chautauqua Institute - 14 miles Chautauqua Lake Pops- 18 miles Holiday Valley - 40 miles Peek & Peak - 18 miles Salamanca Casino - 35 miles

5 out of 5 average rating, 118 reviews

A welcoming living space features a large screen TV mounted on a pale wall, surrounded by a black entertainment unit. A cozy couch with patterned throw pillows faces the TV, while warm wood flooring adds a homey touch. A door leads to the entrance.

Home in Asheville

Lovely 2 bedroom 1 bath country cottage on 5 acres

LOCATION LOCATION LOCATION... This cozy home is close to everything. Located just 2.5 miles from Chautauqua Lake, 10 miles from The Chautauqua Institution, 19 miles from skiing this is the perfect place. THE SPACE... First floor laundry, full kitchen, large screen tv featuring YouTube TV, gas grill and much more. Everything you need to feel at home. NOTE: THERE IS ROOM FOR 4 TO SLEEP, FEATURING TWO QUEEN BEDS AND A LARGE STANDARD (non pullout) COUCH TO SLEEP ON. NO GARAGE ACCESS

4.96 out of 5 average rating, 476 reviews

A cozy living room features two grey sofas adorned with colorful cushions, complemented by a wooden coffee table. A decorative fireplace is centrally positioned against a green wall, while shelves holding books and art pieces are mounted beside it. Natural light is welcomed through large windows with patterned curtains.

Flat in Jamestown

Thurston Terrace Apartment in Downtown Jamestown

Our 19th-century row house apartment has been thoughtfully designed to provide a comfortable stay and authentic local experience on your next visit to Jamestown. Perfectly located in the heart of downtown Jamestown, you can easily walk to excellent restaurants, pubs, and boutique shops, including a café and beer + wine lounge right downstairs. Explore the National Comedy Center, visit the Lucille Ball Desi Arnaz Museum, and head to Chautauqua Lake for scenic walks.

4.95 out of 5 average rating, 339 reviews

A spacious living area is presented, featuring comfortable seating options including a sofa and two armchairs. A television is mounted on the wall, and a lighted floor lamp adds warmth. Large windows allow natural light to illuminate the space, enhancing the cozy atmosphere.

Flat in Jamestown

Chautauqua Lake-View, 2BR Apt w/Full Kitchen

Our fully furnished, family & dog friendly, lake view apartment is waiting for you. Come enjoy lake views, garden walks, and our open concept, eco living space. The apartment is situated on a quiet street perfect for dog walks & bike rides and conveniently close to restaurants, the highway, and nearby tourist destinations. We will try our best to accommodate reasonable early check ins when requested, dependent on our full-time work schedules.

4.88 out of 5 average rating, 195 reviews

A charming ranch-style house is set against a bright blue sky, surrounded by well-maintained greenery and landscaped shrubs. A welcoming front porch features rocking chairs, and an American flag hangs proudly from the front. A gravel pathway leads to the entrance.

Home in Bemus Point

Chautauqua Lakehouse with a picturesque view

Tastefully decorated with lake charm. Minutes from Bemus Point and Downtown Jamestown. Across the lake from Lakewood and the new Chautauqua Harbor Hotel. A short drive to the Chautauqua Institute. Enjoy morning coffee and evening drinks on the front porch. Also a nice winter getaway. On the snowmobile trail. Holiday Valley Ski Resort -40 miles Peak &Peak Ski Resort - 30 miles Cockaigne Ski Resort - 18 miles Salamanca Casino - 35 miles

Guest suite in Bemus Point

An open-concept living area is displayed, featuring a cozy gray sofa and a dining table surrounded by green chairs. White shiplap walls and a high ceiling with exposed beams create a bright atmosphere. Kitchen appliances and decorative elements complement the design.

4.97 out of 5 average rating, 115 reviews

Luxury Suite at The Cottages - Sauna & Hot Tub

Make some memories at this unique and family-friendly retreat in beautiful Bemus Point! The Luxury Suite at The Cottages is a stylish 3 bedroom 2 bathroom unit featuring an indoor sauna in the master bathroom and a hot tub off the back deck. Our goal is for our guests to feel relaxed and rejuvenated at this four season getaway.

A stunning sunset is captured over the calm lake, casting warm hues of orange and pink across the sky. The tranquil water reflects the vibrant colors. In the foreground, the silhouette of a fence and a nearby dock can be seen, enhancing the serene lakeside setting.

4.98 out of 5 average rating, 168 reviews

Welcome Permit

Cozy lakehouse with 100 feet of lakefront. Enjoy this deck with covered gazebo and large fenced in side lot. Great for entertaining. Beautiful covered balcony upstairs overlooking the lake. Many amentities included, such as a private dock, gas grill, cornhole game, firepit and firewood. Pet friendly!!

A renovated ranch home is presented in a serene country setting, surrounded by ample grassy areas. Trees frame the property, which features views of woods and a pond in the background. The house's blue exterior complements the clear sky and natural landscape.

4.95 out of 5 average rating, 165 reviews

Kama Kottage

Totally renovated ranch home with brand new kitchen, kitchen appliances and tiled walk in shower. Quiet country setting with beautiful views of woods and a pond. 11 acres and a primative cabin and woods to explore. Close to both Falconer, NY and Jamestown NY.

4.96 out of 5 average rating, 169 reviews

The kitchen features warm wood cabinetry and modern appliances, including a black refrigerator and microwave. A central island with seating for four is highlighted, while decorative plants and a vase of orchids add a touch of elegance to the space.

Flat in Jamestown

A View From Above

Beautiful apartment in the heart of downtown. Great views of the city and within walking distance of all downtown attractions. Within blocks of The National Comedy Center, The Lucy-Desi Musium, the ice arena and The Reg.

4.94 out of 5 average rating, 291 reviews

A single-story house with a red metal roof is situated in a spacious yard surrounded by lush greenery. Flowering shrubs frame the entrance, and a paved driveway leads to the front door. Large windows allow natural light into the living spaces.

Cottage in Bemus Point

Country escape

This is a complete house, entirely remodeled, having a large yard and surrounded by beautiful wilderness, one mile from Lake Chautauqua

Popular amenities for Jamestown family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 169 reviews

A newly constructed cabin is nestled among lush trees, showcasing a wooden exterior. Adjacent to the cabin is a picnic shelter that includes an Amish-made dining table. A circular fire pit is set on a stone patio, providing an inviting outdoor gathering space.

Cabin in Cattaraugus

Hot Tub BBQs Fire Pit Trails Birds New Build

4.99 out of 5 average rating, 128 reviews

The chalet stands amidst lush greenery, showcasing a large wrap-around deck with outdoor seating and an umbrella. A stone fire pit surrounded by red Adirondack chairs is positioned on the lawn, offering a welcoming space for gatherings.

Chalet in Ellicottville

Pines Chalet in Ellicottville ~ Hot Tub~Fireplace

4.98 out of 5 average rating, 104 reviews

A geodesic dome is set in a lush outdoor space, surrounded by trees. A spacious wooden deck features a hot tub and patio furniture, inviting relaxation. The dome's distinctive shape is complemented by large triangular windows that provide ample natural light.

Dome in Youngsville

Riverfront Dome with Hot Tub

4.98 out of 5 average rating, 101 reviews

The living area features natural wooden walls and a vaulted ceiling, with a comfortable sofa and a coffee table positioned on a patterned rug. A staircase with ladder-style steps leads to the loft, while a red refrigerator is visible in the kitchen area.

Cabin in Sherman

Rustic Retreat

4.86 out of 5 average rating, 175 reviews

Chalet in Little Valley

Privacy on the Mountain, Ellicottville.

4.92 out of 5 average rating, 212 reviews

Cabin in Cassadaga

Angies The Love Shack with shared hot tub access

5 out of 5 average rating, 111 reviews

The cabin exterior features natural wood shingles and large windows, providing a warm and inviting appearance. A stone pathway leads to the entrance, bordered by well-maintained landscaping and vibrant plants, surrounded by greenery that enhances the tranquil setting.

Home in Mount Jewett

The Hills and The Holler (Westline)

4.98 out of 5 average rating, 130 reviews

A stylish chalet stands nestled among tall green trees, featuring a prominent stone chimney and a large deck that extends from the structure. Windows reflect the natural light, blending the home with its serene forest surroundings.

Home in Ellicottville

Private Cozy Hideaway w/Hot Tub - Hike from Cabin!

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 129 reviews

A landscaped exterior showcases vibrant flower beds in a variety of colors, bordered by well-maintained greenery. The view extends to Lake Erie, with calm waters reflecting the sky. A spacious deck is visible in the background, providing an area for relaxation and enjoying the scenery.

Home in North East

Lakefront Escape

4.96 out of 5 average rating, 136 reviews

An open floor plan features a queen bed with light bedding, complemented by a cozy couch and armchair. Large windows allow natural light to brighten the space, while wooden beams add character to the ceiling. A small coffee table and decorative plants enhance the inviting atmosphere.

Cottage in Portland

Lake-View Cottage for 4 · Wine Tasting Included

4.98 out of 5 average rating, 181 reviews

The exterior of a spacious home is shown, featuring a welcoming porch with seating. Lush greenery and colorful flower beds surround the house. A manicured lawn enhances the curb appeal, while power lines run along the road adjacent to the property.

Home in Bemus Point

W.G. Summer House by the Lake

4.99 out of 5 average rating, 251 reviews

A canoe glides across a calm pond, framed by trees showcasing autumn foliage. Two people paddle gently, surrounded by vibrant reflections of fall colors on the water's surface. A clear blue sky enhances the serene atmosphere, inviting exploration of the tranquil landscape.

Home in Randolph

Quiet Convenience

4.92 out of 5 average rating, 153 reviews

A spacious single-story home is set back from the road, surrounded by a large lawn adorned with shrubs and trees. A gravel driveway leads up to the house, which features a red roof and multiple windows. Bright green grass encloses the property, providing a serene country atmosphere.

Home in Dewittville

Chautauqua Lake LilyDale Wineries Comedy Fishing

4.97 out of 5 average rating, 244 reviews

Cabin in Clarendon

🌲Rustic Run Cabin in the Allegheny National Forest

4.84 out of 5 average rating, 116 reviews

An old farm house is framed by towering trees, showcasing vintage wooden siding and a welcoming front porch. Lush green grass surrounds the home, reflecting natural beauty during sunrise. The peaceful rural setting is enhanced by gentle sunlight filtering through the branches.

Farm stay in Sugar Grove

Patchen Hill Farm House, Tree Farm, & Arboretum

4.94 out of 5 average rating, 124 reviews

The kitchen is organized with dark cabinetry and white countertops, featuring a stove and sink. A window allows natural light to illuminate the space, with a small dining table and two chairs positioned nearby. A refrigerator stands against one wall, complemented by decorative items above.

Flat in Fredonia

My Blue Haven

Family-friendly home rentals with a pool

4.86 out of 5 average rating, 21 reviews

A pathway leads to a patio area with an umbrella, providing a shaded seating option. Lush greenery, including tall evergreen trees and neatly trimmed bushes, frame the natural surroundings, while the vibrant yellow exterior of the house offers a welcoming contrast.

Flat in North Harmony

Chautauqua Lake Beauty

4.96 out of 5 average rating, 24 reviews

Home in Mayville

Chautauqua Retreat: 5 Private Acres. Heated Pool.

5 out of 5 average rating, 24 reviews

Home in Mayville

The Plum Bush House: Victorian farmhouse retreat

5 out of 5 average rating, 157 reviews

Farm stay in Cattaraugus

The Guest House at Burdick Blueberries Farm

4.87 out of 5 average rating, 149 reviews

The living area features a comfortable arrangement with a sofa, two armchairs, and a wooden coffee table. A fireplace is situated beneath a wall-mounted television, complemented by two windows that allow natural light. Decorative elements include lamps and wall art.

Apartment in Clymer

Adorable Ski/Golf Condo at Peak N Peek

Superhost

An outdoor hot tub is positioned on a wooden deck, with gentle bubbling water visible. Surrounding the tub, hanging light fixtures offer illumination, and a scenic view of rolling hills and trees is present in the background, suggesting a peaceful atmosphere at sunset.

Home in Ellicottville

4.92 out of 5 average rating, 39 reviews

Hot Tub & Views! The Eagles Nest, Couples Escape

4.92 out of 5 average rating, 64 reviews

A well-equipped kitchen is presented with white cabinetry and granite countertops. Stainless steel appliances, including a microwave and oven, are visible. A dining table with dark chairs is set for several diners, while bright overhead lighting accentuates the vaulted ceiling.

Home in Mayville

Spacious Chautauqua Lake 4 Bedroom home