Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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

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Superhost

A covered patio features comfortable seating under a shelter, with striking stone landscaping in the foreground. The home's white exterior is complemented by greenery, including trees and shrubs in the background, providing a welcoming entrance.

Apartment in Newstead

4.88 out of 5 average rating, 133 reviews

THE PEACEABLE NEST - Buffalo/Niagara Akron, NY

Relax and unwind with friends here! THE PEACEABLE NEST is a 3 bedroom unit with Spa Sensations beds and hypoallergenic bedding for your comfort and rest. 4 mins to Sterling, Timberlodge & Akron Acres wedding venues! Full kitchen equipped with everything you need for your time away! The covered patio overlooks a pastoral view for morning coffee or evening drinks. Nearby Akron has restaurants & take-out, also try Kaboodles Kafe two doors away! The Nest is prepared for your comfort and pleasure!

Top guest favorite

Barn in Perry

4.98 out of 5 average rating, 259 reviews

Boutique Barn Near Letchworth + Animal Encounters

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 favorite

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, 45 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 favorite

Home in Attica

5 out of 5 average rating, 13 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.

Guest favorite

Home in Holland

4.9 out of 5 average rating, 10 reviews

Upscale living on Organic Farm

This is no ordinary farmhouse, but rather an upscale resort facility boasting Brazilian teak floors, expansive quartz countertops, a unique live-edge kitchen table, top-notch leather furniture, plush mattresses, modern bathrooms, and amazing views from every window. Outside there is a three acre lake with a white sand beach, kayaks, forest walking trails, a formal flower garden, an amazing Victorian glass greenhouse with built-in aquariums, and all the fresh in-season fruit you care to pick.

Top guest favorite

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.

Apartment in Clarence

4.99 out of 5 average rating, 161 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 favorite

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 Giant Heated Pool Buffalo, NY

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 favorite

Guesthouse 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.

Top guest favorite

A kitchen area features wooden cabinets and a countertop with essential appliances, including a microwave and toaster oven. A small table with a white surface sits by a window, adorned with a vase of flowers. Two wooden chairs are positioned around the table.

Guesthouse in Wyoming

4.97 out of 5 average rating, 114 reviews

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.

Guest favorite

A bridal gown is elegantly displayed on a hanger in a well-lit room. A large vintage mirror reflects the space, which features a cozy seating area with a leather sofa and a decorative circular rug. Natural light filters through sheer curtains, enhancing the inviting ambiance.

Home in Elma Center

5 out of 5 average rating, 32 reviews

Full House Rental with a focus on Wedding Day Prep

Welcome to Blanc Silk! We are a house rental with a focus on Wedding Day Prep. 👰‍♀️ We also welcome Buffalo Bills and Football Fans! 🏈 Approximately 15 mins from the stadium! Our spacious and unique home is perfect for wedding day bridal preparations and Bill games! Our house Includes a bridal suite along with a separate beauty styling lounge. When staying with us, your rental includes, outdoor property, gardens and ground for fabulous photo opportunities.

Guest favorite

The exterior of the historic colonial home features a welcoming facade, with an American flag displayed prominently. Lush greenery surrounds the entryway, enhanced by flowering planters. A decorative black fence encloses a well-maintained lawn, creating a charming and inviting atmosphere.

Guest suite in Corfu

4.93 out of 5 average rating, 41 reviews

Iron Gate Property

Unwind in this Historic 1863 colonial style home. Fully restored three bedroom and two bath suite. Located in between Rochester and Buffalo, a quick 5 minute drive off of the thruway in the small quaint village of Corfu. 5 minute drive to Darien Lake Theme Park/ Live Nation Theater and Darien Lake State Park. *No kitchen/hotel like setting Other treasures within 45 minute drive or less include Letchworth State Park, Niagra Falls, wineries and Breweries

Guest favorite

An open-concept kitchen and dining area is illuminated by recessed lighting. A dining table with four chairs stands beside a large window, which offers views of the deck outside. A modern kitchen with stainless steel appliances and a central island can be seen, enhancing the space's functionality.

Guesthouse in East Aurora

4.96 out of 5 average rating, 46 reviews

The Overlook

Welcome to The Overlook! Stay in a relaxing guesthouse that sleeps 4, with beautiful, serene views. Located just 9 minutes from historic village of East Aurora, 23 minutes from Orchard Park (home to the Buffalo Bills stadium), and 27 minutes from Downtown Buffalo. In East Aurora, enjoy boutique shopping, as well as many local favorite spots to eat. Spend a day in nature hiking at Hunter's Creek County Park or enjoy the countryside at Knox Farm State Park.