Holiday rentals in Bennington

Front and Center

Warm and cozy home from the turn of the century. Well maintained with all original wood trim. All bedrooms and bath upstairs on second floor. Appliances, dishes and everything you need to make a meal. Open front and back porches and a big back lawn. Short walk to a movie theater, home-made ice cream, great restaurants and a brewery. 20 mins to Letchworth State Park, 15 mins to Silver Lake, 1 1/4 hours to Niagara Falls. Near Class A Trout streams. No extra cleaning fee (just don't leave a mess)

Boutique farm overlooking Letchworth State Park!

✨ Unique Barndominium Conversion ✨ Dell Collective - Check us out! ✨ Friendly Farm animals on property- Meet our Camel Sandy + Zebra Maisy! ✨ 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 ✨ Minutes to Main Street in Mount Morris ✨ 1.5 Hours to Niagara Falls ✨ Book a Hot Air Balloon Flight, go rafting or horse riding nearby!

"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 dog Toby & our cat Taffy who will welcome you (but will not be a bother) we invite you to enjoy our home.

The Knotty Pine a Romantic Getaway

Our home is a warm and welcoming cabin located 5 minutes from Kissing Bridge ski resort and a short walk to Sprague Brook Park. The park offers three stocked fishing ponds plus hiking and bike trails. It's a 35-minute drive to Buffalo, a 15-min drive to historic East Aurora, 25 minutes to Highmark stadium, and an hour to Niagara Falls. You will have entire access to the cabin,which includes a master bedroom, full kitchen, living room, loft, and bathroom. The cabin is enjoyable year round.

Bungalow in Bliss

Enjoy beautiful views from this quaint bungalow, perched on a hillside in the heart of farm country in Wyoming County, NY. Open concept space. Modern appliances. Retro lighting. Adirondack style furniture. Plenty of windows for natural lighting. Enjoy the panoramic view of the sunrise, sunset on the huge, private deck. Plenty of restaurants, convenience store, small towns in any direction, lake, river, parks and hiking trails nearby. Plus, enjoy Letchworth State Park just minutes away!

The Red Roof Lodge!

Enjoy a peaceful retreat at the Red Roof Lodge in Wyoming, NY! The apartment-style guest house is located above the barn. It's a perfect location for a tranquil getaway. Tucked away just off the beaten path, you'll find yourself surrounded by the sounds of nature. Unplug and enjoy morning walks along on-site walking trails, shower under the stars in the outdoor shower or visit nearby attractions like Niagara Falls, Letchworth State Park, Six Flags or the quaint town of Warsaw.

Large 2 bed 2 bathroom loft in East Aurora Village

Centrally located in the heart of East Aurora, this loft style apartment is one of one! That means the entire top floor of the building is yours and completely private. This unit features 2 bedrooms (king and queen beds) and 2 full bathrooms. You’ll enjoy the high end finishes and A+ views overlooking the village. This home is large so there is privacy. Feels like 2 apartments in one if you’re traveling with friends or children to have your own space, separate bathrooms etc!

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

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

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*

Charming 2 bedroom cottage on the EA golf course

Welcome to Maplelinks. Relax at this quiet and quaint 100 year old 2 bedroom/1 bathroom guest cottage located right on the East Aurora Country Club less than a mile outside of the village. 15 minutes from Bills games. 20 minutes from downtown Buffalo. 20 minutes from skiing. Private off street parking. Self check-in anytime after 3pm. (Sorry. No pets.)

Cozy apartment near entrance to Letchworth Park.

This space is in the perfect location--10 minute drive to the Letchworth State Park, and one mile to Silver Lake, walking distance to the downtown area of Perry. 15 minute drive to SUNY Geneseo. Apartment has parking and great amenities. High speed WiFi is available!