Holiday rentals in Bennington

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Top-rated holiday rentals in Bennington

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

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Top guest favourite
Barn in Perry
4.98 out of 5 average rating, 258 reviews

Boutique Barn- Letchworth, Animals, Tub + Fire Pit

Welcome to Highbanks at the West Barn, by Dell Collective ✨ Unique Barndominium Conversion ✨ Dell Collective - Check us out! ✨ Friendly Farm animals on property- Meet our Camel Sandy ✨ Chef's Kitchen ✨ Waterfall Showers + Soaking tub ✨ Smart TV + Fast Starlink Wifi ✨ 1 King bed, 1 Queen Bed, 1 Sofa bed ✨ Laundry ✨ Moments from Letchworth State Park ✨ Minutes to Silver Lake or Main Street in Perry ✨ 1.5 Hours to Niagara Falls ✨ Book a Hot Air Balloon Flight, go rafting or horse riding nearby!

Top guest favourite
A welcoming entryway features light gray walls and a natural wood floor. A console table with decorative accents stands against the wall, complemented by a mirror. Natural light filters through the front door, which is adorned with a simple wreath.
Home in Akron
5 out of 5 average rating, 44 reviews

Home Sweet Akron

Relax and unwind in this brand new 3 bedroom home furnished in a beautiful modern farmhouse theme. Located within walking distance to the Akron/Clarence bike path and a 5 minute drive to Timerlodge, The Sterline and Akron Acres wedding venues. Home has an attached deck overlooking a pond to enjoy your morning coffee or a glass of wine @ sunset. The village of Akron is host to several resaurants and quaint shops. A park is situated right in the cente of town featuring a splash pad and gazebo.

Guest favourite
Home in Attica
5 out of 5 average rating, 11 reviews

Cute country cottage…

Enjoy the country at this cute cottage with lots of amenities. Whether a couples getaway, family vaca, girls weekend, or snowmobile trip, this property has what you need. Property sits on 4 acres, has an open floor plan & large lawn. Grill, drink wine, have camp fires, snowmobile, and/or visit some of WNYs great destinations. Close to Batavia, Darien Lake, Byrncliff, snowmobile trails, golf courses, restaurants, several breweries, and grocery store. The Bills & Letchworth are within 45 min.

Top guest favourite
A comfortable living area features a cozy fireplace set within a brick accent wall, providing a focal point. A large TV is positioned nearby, while a soft leather sofa and a vibrant orange chair offer ample seating. Natural light enters through the windows, enhancing the inviting ambiance.
Flat in Clarence
4.99 out of 5 average rating, 160 reviews

Meticulous Main St. Ranch 2 Bd Lux Apt. Rear Unit

This well-appointed, recently renovated, 1200 sq. ft. ranch duplex apt. is located on Main St in the heart of charming & historic Clarence, NY. The community is a beautiful, safe, and family friendly suburb of Buffalo, NY. The entire apt. is on one level, with four parking spaces next to the entrance. The beautiful open concept floor plan provides an abundance of natural lighting, creating a comfortable airy feeling, that is perfect for small gatherings, business travelers, and entertaining.

Guest favourite
A charming cabin nestled among tall trees showcases a grassy lawn in the foreground. The structure features a covered porch and large windows, blending harmoniously with nature. Soft sunlight filters through the branches, casting gentle shadows on the ground.
Cabin in Warsaw
4.94 out of 5 average rating, 32 reviews

Cozy Cabin Getaway on a Scenic Horse Farm

Our cozy cabin is a 1 bedroom, 1 bathroom that is perfect for a romantic getaway. Tucked back in the woods, it is the perfect place to unwind for the night. Our cabin is equipped with a full size fridge/freezer, kitchen, TV, AC, heat, and large living room. Our deck has a outdoor kitchen with a fridge, grill and a fireplace. The view that is offered at our cabin is like no other. This cabin is on the same property as a working horse farm. We also offer guided horseback rides to the public.

Guest favourite
A fenced-in area showcases a private heated pool surrounded by lush greenery and blooming flowers. Lounge chairs are positioned nearby on the patio, providing a space for relaxation. The pool features clear water and is well-maintained, inviting guests for a refreshing swim.
Home in Alden
4.91 out of 5 average rating, 118 reviews

Carols Country Inn ☆☆☆☆☆

Do you enjoy luxury? You and your family have our entire home to enjoy sleeps 5 Features : piano, fireplace, fenced in pool :vaulted gazebo Our home includes 3 bedrooms (queen beds) , 2 baths, master suite has bath Deep soaker tub & shower, washer/dryer a beautiful gazebo at the poolside , charcoal grill available, inground private heated pool. pool open may 28 2024 Our home is short drive to falls approx 40 mins Uber to Buffalo Niagara airport in 18 m Darien Lake (15 min

Guest favourite
Guest house in Strykersville
4.79 out of 5 average rating, 14 reviews

Jenn's Piece of Paradise Resort

Discover an enchanting destination specifically crafted for lovers seeking intimacy and relaxation. Unwind in our fully remodeled, romantically furnished, farmhouse themed home. Experience privacy with an inviting jacuzzi in your living room or enjoy breathtaking views from the outdoor hot tub. Our goal is to provide a serene atmosphere perfect for enjoying each other's company. Private access to the entire Bed and Breakfast, including three separate rooms upstairs for your enjoyment.

Guest favourite
A cozy bedroom features a wooden sleigh bed with a plaid comforter. A decorative lamp sits on a nightstand beside the bed. A trunk labeled 'LOVE' is placed at the foot of the bed, and a window with a checkered valance allows natural light to filter in.
Guest suite in Lancaster
4.96 out of 5 average rating, 199 reviews

"The Suite Spot", Adorable apartment with deck

Kick back and relax in this calm, stylish space. This second floor apartment boasts a newly remodeled bathroom, a full kitchen, a comfortable bedroom perfect for two & a cozy sitting area with chairs that convert into twin beds. It also offers off street parking for one vehicle & a private entrance on the deck. It's a perfect place to relax & enjoy the summer & fall. Along with our cat Taffy who will welcome you (but will not be a bother) we invite you to enjoy our home.

Top guest favourite
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, 167 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 favourite
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, 124 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 favourite
A spacious balcony extends from the second floor, featuring two outdoor chairs and a small table. The view showcases a lush green lawn leading to the lake, framed by residential houses and trees under a clear blue sky.
Cottage in Fort Erie
4.96 out of 5 average rating, 145 reviews

Steps to the Beach + Lakeviews + HotTub + Elevator

Unwind at this The Red Lakehouse just steps from the beach, featuring a private hot tub, fire pit, and covered balcony with Lake Erie views. Perfect for families, groups, and getaways, this professionally designed home offers 3 bedrooms with private ensuites for ultimate comfort and privacy. Minutes to Niagara Falls, Crystal Beach, and the USA border — yet tucked in a quiet, relaxing neighbourhood. A spotless, thoughtfully curated stay.

Top guest favourite
A comfortable living area features a gray sofa adorned with decorative pillows. Nearby, a round leather ottoman complements a patterned rug. A tall floor lamp provides soft lighting, and a potted plant adds a touch of greenery to the space. Artwork is displayed on the walls.
Flat in Strykersville
4.99 out of 5 average rating, 270 reviews

Suite and Simple - Private 3rd Floor Efficiency

Suite and Simple is a private, upstairs suite on a quiet country hillside. It is 15 minutes from the village of East Aurora, about 30 minutes from downtown Buffalo and minutes from local wedding venues. Whether you're just passing through, or in town for an event, this suite has the essentials for a restful stay. *There are 2 flights of stairs to get to the suite*

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