Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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Top guest favorite
Two wooden Adirondack chairs are positioned around a circular firepit, with a cozy blanket draped over one. Behind, the geodome is seen beside a tranquil pond, surrounded by lush greenery, reflecting a clear blue sky.
Dome in Port Colborne
4.99 out of 5 average rating, 587 reviews

Luxury Romantic Glamping Dome near Niagara Falls

You'll love this unique and romantic escape for 2, located 30 minutes from Niagara Falls in Port Colborne. Our 400 sq ft geodome offers all the amenities needed for a relaxing, romantic getaway. Panoramic floor to ceiling window over looking a private pond with the opportunity to see wildlife from the comfort of inside the dome. Enjoy a fireplace, hot tub, comfy queen size bed, private deck with a fire table, outdoor shower, firepit on your own island, incinerating indoor toilet, AC, and wifi.

Top guest favorite
A spacious loft area features a cozy sleeping space with a large bed, complemented by a decorative light fixture overhead. A television is positioned for viewing, and natural light fills the area through multiple windows. A comfortable seating area and soft textures contribute to the serene environment.
Loft in Niagara-on-the-Lake
4.9 out of 5 average rating, 504 reviews

Luxury In The Heart Of Wine Country

Hidden along the shores of the Niagara River, Grayden Estate is nestled on a quiet dead end street in beautiful Queenston/Niagara on the Lake. A short drive to Old Town and within a few minute walk or bike to world class wineries, art galleries, farmers markets, hiking trails, parks and the waterfront, Grayden Estate is the ideal location for a peaceful quiet getaway for anyone looking to surrender to the simple living quiet life. Complimentary tour bikes are available for use. Lic # 112-2023

Top guest favorite
Castle in Elmwood Village
4.9 out of 5 average rating, 290 reviews

King Fireplace Luxury Loft Gym Bball EV+

Experience the unique luxury! Perfect for family, business, or romantics. With high end finishes, 16' ceilings, a stunning 6' fireplace, this space exudes comfort & elegance. Unwind in the 5' round tub, or enjoy a movie on the 85' smart tv, while appreciating the building's history. For the active guests, an indoor basketball court and gym. Office area for business travellers. Seasonal rooftop area for sunsets or enjoying the weather. Additional bedrooms can be added for larger groups.

Top guest favorite
The exterior of the cottage features warm wooden siding, complemented by large windows that provide views of the surrounding nature. Two skis are mounted on the wall, hinting at outdoor recreational activities. Lush greenery and a small deck are visible next to the cottage.
Cottage in Fillmore
4.97 out of 5 average rating, 231 reviews

Iris Cottage, Nature on Higgins Creek

Iris cottage is set on a quiet road in WNY just 15 mi. from Letchworth State Park and 5 mi. from Houghton College. Gas fire place greets guests on chilly days and a large deck overlooks woods and Higgins Creek. The kitchen is well stocked and fully equipped. Whether summer or winter this is the perfect place to enjoy WNY nature at its best and get away from it all. 2 bedrooms open to open plan living, kitchen and dining. Onsuite master has a second electric fireplace and deck access.

Top guest favorite
The interior of the suite features warm wood accents and a combination of natural light and soft lighting. A spacious living area is furnished with a comfortable chair, while an inviting kitchenette is visible in the background. A rustic decor piece stands along one wall, enhancing the cozy ambiance.
Guest suite in Springville
4.99 out of 5 average rating, 217 reviews

Hallmark like cabin suite with panoramic view

Take it easy at this unique and tranquil getaway. Perfect for one or two Adults. Comfortable King Size Bed, private bath, kitchenette (not a kitchen) with airfryer/toaster oven, microwave and keurig. Take time away from the hustle and bustle and stay closer to nature in this lovely private suite. Linens, towels and numerous kitchen items provided. Plenty of popular activities and scenery in the surrounding towns and villages. Complimentary WIFI is available but can be unreliable.

Top guest favorite
A comfortable living area features a blue sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, complemented by a potted orchid and a bottle of wine. A gallery wall with artwork adds personal touches alongside a bookshelf filled with curated decor.
Home in Niagara-on-the-Lake
4.98 out of 5 average rating, 141 reviews

Enchanted Creekside Cottage in NOTL

Welcome to Enchanted Creekside House! Our tranquil cottage is nestled alongside a creek, offering the perfect location for a peaceful family getaway. Enjoy the serene beauty of nature while still being just a short 9-minute drive from the heart of Niagara-on-the-Lake, where you can explore charming shops, restaurants, and a variety of wineries. Enchanted Creekside House is the perfect home base. Whether you're looking to unwind and recharge, or seeking adventure and exploration!

Top guest favorite
A welcoming exterior view of a remodeled country home is showcased, featuring a screened porch with dark trim and a white door. Lush greenery surrounds the property, complemented by freshly landscaped flower beds and a gravel pathway leading to the entrance.
Home in Perry
4.97 out of 5 average rating, 157 reviews

Peaceful Country Home

A peaceful clean home for you to enjoy!! We have a very nice size yard for camp fires and just relax in without any neighbors.Welcome to a peaceful country home in the middle of several very large ponds. Relax on the covered screened porch or the back deck for peaceful meals or just some bird watching. Not super far off the road but you feel like it. Road is pretty quiet and lots of wild life. Ponds and woods not our property so please stay in yard/ grass only

Top guest favorite
The exterior of the timber-frame home is shown, featuring large two-story windows and wood accents. A covered veranda extends from the structure, offering seating. Surrounding greenery and manicured grass enhance the natural setting, inviting a peaceful retreat in the countryside.
Home in East Aurora
4.98 out of 5 average rating, 121 reviews

Timber-frame home on 12 wooded acres

Featured in Buffalo Spree and Artvoice, this timber-frame home features stunning hickory and black walnut interiors illuminated by two-story windows that face the morning sun. Radiant floor heating and earthen-plaster climate design. Wake up in queen and king beds, lounge under covered verandas, and shop right next door at Thorpe’s organic farm store. • 7 minutes from the Village of East Aurora • 24 minutes from Bills stadium • 1 hour from Niagara Falls

Top guest favorite
A bright bedroom features a spacious bed with layered bedding and decorative pillows. Two nightstands with lamps are positioned beside the bed. Artwork hangs above the bed, and a large window is dressed with sheer curtains, allowing natural light to fill the room.
Apartment in West Falls
4.95 out of 5 average rating, 106 reviews

Spacious kid friendly apt near East Aurora

Stylish, newly renovated upper unit offering 2 bedrooms (including full-size bunk beds) and a queen pull-out sofa. Nestled beside the serene Blueberry Treehouse Farm and just moments from East Aurora’s charming Main Street. Enjoy easy access to Orchard Park, Ellicottville, Downtown Buffalo, Highmark Stadium, Chestnut Ridge Park, and more. Ideal for a relaxing retreat or upscale getaway. Complimentary parking included.

Top guest favorite
The studio features an open layout with a cozy seating area including a gray sofa and matching chairs. A dining table accommodates four, and a spacious bed is present in the corner. Natural light filters through the window treatments, highlighting the neutral color scheme.
Guest suite in Lancaster
4.91 out of 5 average rating, 192 reviews

Work or Play this is your Home Away!

Newly remodeled private studio with private entrance. Lots of parking space. 700sq ft.of living space for you to enjoy! Private balcony overlooking stunning backyard views with a pond. Only 13 min away from Buffalo airport! Shopping centers within a mile. Downtown Buffalo- 20 min. drive Flix Movie Theater- 2 min. drive New Era field- 20 min. drive Niagara Falls- 40min. drive Galleria Mall- 12 min. drive

Top guest favorite
A charming cabin exterior is presented, featuring a welcoming porch with seating and a doorway illuminated by warm light. The structure is surrounded by lush greenery, showcasing a tranquil setting. A separate utility shed can be seen to the right of the cabin.
Cabin in Dansville
4.98 out of 5 average rating, 149 reviews

Pine Hill Hideaway

Pine Hill Hideaway is your romantic escape in the woods and adventure haven in NY’s Southern Tier—just 25 mins from Letchworth State Park and steps from thousands of acres of state forest and wildlife management areas. This cozy luxury cabin features a queen bed, sleeper sofa, kitchen, 3/4 bath, and new AC for warmer months. Hike by day, stargaze by night. Weekend stays book 2–4 months out—reserve early!

Guest favorite
The Cape Cod style home features a well-maintained front yard with a manicured lawn and blooming landscaping. A stone pathway leads to the entrance, flanked by two large windows with blue shutters. An American flag adorns the front porch, adding a welcoming touch.
Home in Batavia
4.89 out of 5 average rating, 193 reviews

Livia's Landing At The Golf Course

Golf Course View in a Small Town Feel This beautiful Cape Cod style home is located conveniently between Rochester, NY and Buffalo, NY, just off from NYS I-90 Thruway. This newly remodeled home with a lot of updates inside out and amenities. This home is located a few steps away from Terry Hills Golf Course (the backyard is the golf course), Batavia Country Club, and a beauty salon.

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