Holiday houses in Lakewood

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Top-rated holiday rentals in Lakewood

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

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.

4.97 out of 5 average rating, 125 reviews

Superhost

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.

Home in Jamestown

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

4.84 out of 5 average rating, 135 reviews

Top Guest favourite

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 Ashville

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

5.0 out of 5 average rating, 136 reviews

Top Guest favourite

A dining area is presented with a rustic wooden wall and a mix of dining chairs surrounding a light wooden table. Natural light enters through nearby windows, illuminating the space, complemented by a black front door and a decorative chandelier overhead.

Place to stay in Lakewood

Cozy Boutique Stay Steps from Chautauqua Lake

Make yourself at home. Unwind & be sure to enjoy the porch, an outdoor fire, take a walk to enjoy the lake views. Enjoy a record player, hand selected books, games, upscale coffee, & cozy nooks. This space features vintage wares and fun items collected on our travels. You will sink into comfy beds while sleeping soundly surrounded in quality linens. Vintage table fans are in each bedroom, and you will enjoy a rainfall shower with luxury amenities. Truly a one of a kind experience!

5.0 out of 5 average rating, 40 reviews

Guest favourite

The kitchen features wooden cabinetry and a large island with two stools. A white refrigerator and appliances are visible, along with a window allowing natural light. The entryway is seen in the background, showcasing a front door and tiled floor.

Cottage in Lakewood

Spacious Cottage With Lake View

Welcome to our lake house on the one and only Chautauqua Lake! Many of the reviews for this listing can speak for themselves - in short, you are guaranteed a cozy, lakefront experience perfect for travelers traveling in small or large groups. The house is located walking distance to the town’s main road with convenience stores, shopping, coffee shops, restaurants, local mall, parks, etc. The sunrise and sunset views from the back windows will leave you breath taken!

4.86 out of 5 average rating, 106 reviews

Top Guest favourite

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.

Apartment 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.

4.97 out of 5 average rating, 487 reviews

Top Guest favourite

A cozy living area features a fireplace as the focal point, framed by a wooden mantel. Light streams through two large windows with white blinds, illuminating the furnishings, including a mix of seating options and a decorative area rug that adds warmth to the space.

Home in Bemus Point

Palli's Place LLC - Cozy Retreat

Relax and recharge at this spacious 3-bedroom, 2.5-bath home near the lake. Perfect for families and groups, it features a fully equipped kitchen, cozy living spaces, and peaceful bedrooms to ensure a comfortable stay. Enjoy your mornings with coffee in the sunroom or sitting by the fireplace. Pallis Place is the perfect mix of comfort and convenience, offering a serene getaway for making lasting memories. Book your stay and feel right at home at Pallis Place!

4.99 out of 5 average rating, 93 reviews

Top Guest favourite

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.

Apartment 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.

4.95 out of 5 average rating, 365 reviews

Top Guest favourite

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

4.88 out of 5 average rating, 206 reviews

Top Guest favourite

Loft in Jamestown

Vintage Trolley Station Now Industrial Style Loft

Enjoy a piece of history when you stay in our former trolley station that has been converted into an industrial style loft. Just outside the city limits in a country setting but close to the hospital, local bars/restaurants and the comedy center. The lower portion of the building features a quaint gift shop and across the street is a farm stand with locally grown food.

5.0 out of 5 average rating, 277 reviews

Top Guest favourite

A light-filled living area showcases large windows with lake views. A cozy, elegant loveseat and two tufted armchairs frame a wooden coffee table, positioned on a soft area rug. A potted plant adds a touch of greenery near the open door leading to the outdoor space.

Home in Jamestown

Cozy Lakefront Cottage

Enjoy and relax with the whole family at this peaceful place to stay. The Chautauqua lake is just a few steps from the backyard. Enjoy fishing, (ice fishing in the winter!) boating, bonfire, bbq, canoeing and breathtaking sunsets are not to be missed! This home is newly renovated and is located near all major shops and amenities. Free parking.

4.99 out of 5 average rating, 149 reviews

Top Guest favourite

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.

Home in Jamestown

Cead Mile Failte- a hundred thousand welcomes!

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!!

4.98 out of 5 average rating, 176 reviews