Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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Top guest favorite

A welcoming front porch features a small round table with two chairs positioned under a covered area. Lush green bushes frame the space, surrounded by a wooden railing and steps leading to the entrance of the home.

Home in Warsaw

4.95 out of 5 average rating, 360 reviews

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)

Guest favorite

A large private deck features several Adirondack chairs facing a scenic view. A small table is positioned at the center, holding a decorative lantern. The sun sets on the horizon, casting a warm glow over the landscape of farms and fields.

Bungalow in Bliss

4.89 out of 5 average rating, 264 reviews

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!

Guest favorite

A charming eat-in bay window features a round wooden table surrounded by four black chairs. Natural light floods the space through large windows adorned with sheer orange curtains, illuminating the wooden flooring and creating a warm atmosphere.

Apartment in West Side

4.94 out of 5 average rating, 190 reviews

Lovely 1 bed 5 min Downtown w/ parking & laundry

Enjoy this beautiful artistically inspired 700sqft 1 bed upper apartment in the heart of the city featuring a gorgeous entry and original architectural details. Decorated in lush romantic jewel tones to be remembered. Located in a historic neighborhood within walking distance to nightlife on Allen, shops on Elmwood & 5 Points. Downtown is only a 5 minute drive away! -Private Entry -AC -Roku Tv w/ guest mode -Hi-speed WiFI -Free off street parking -Free laundry -Cooking essentials

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

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

4.94 out of 5 average rating, 36 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.

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

4.97 out of 5 average rating, 118 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

The spacious living and dining area features a modern dining table with four chairs, an inviting seating area, and a large smart TV mounted on the wall. A colorful accent wall complements the carefully arranged decor, including a decorative fireplace and natural stone accents.

Apartment in Buffalo

4.98 out of 5 average rating, 289 reviews

South Buffalo Zen w/ Private Yoga Studio ॐ

✩ private yoga studio ✩ coffees, teas and spices ✩ 65” smart TV ✩ fully stocked kitchen & bath ✩ fast wifi ✩ 10 min to downtown & <20 min to airport ✩ free street parking ✩ walking distance to Cazenovia Park ✩ 25-35 minutes to Niagara Falls & Canadian Border ✩ Go Bills! (15 min to Stadium) Zen Retreat Buffalo - More than a simple accommodation, it's an unforgettable travel experience.

Top guest favorite

A fire pit area is set in a grassy space, surrounded by five black Adirondack chairs. The area is shaded by trees, with a circular arrangement around the pit, creating a cozy spot for gathering outdoors.

Apartment in Attica

5 out of 5 average rating, 18 reviews

Rural Brookside suite

Welcome, to rural NY , this is a 1 bedroom apartment in our 100 year old family farm house, only a mile from Attica village with shops and dining options. We are a start up elderberry farm situated in rural NY The suite is within an hour of buffalo, Rochester and Niagara Falls. 40 minutes from Letchworth state park And only about 10 minutes from Darian lake theme park

Top guest favorite

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.

Apartment in Strykersville

4.99 out of 5 average rating, 262 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*

Top guest favorite

A charming cottage is set against a vibrant sunset sky, with soft hues illuminating the surrounding trees. The front entrance is framed by a welcoming porch, leading to a grassy area that gradually slopes away from the building.

Cottage in East Aurora

4.91 out of 5 average rating, 195 reviews

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.)

Top guest favorite

A cozy sleeping area features a spacious bed adorned with light bedding. Two bedside lamps provide soft light beside the bed. A vintage-style chair and small side table are present, and large windows are adorned with sheer drapes, allowing ample natural light.

Apartment in Batavia

4.89 out of 5 average rating, 131 reviews

The Cozy Nook

The Cozy Nook is a quiet, serene space for one or two people looking to unwind from the daily chaos of life. Nestled on a quiet street right next to a lovely city park, people can use this space for a weekend get-away, a home away from home while visiting friends and family, and/or a resting spot when traveling.

Guest favorite

A welcoming display is centered on a wooden table, featuring a decorative sign that reads 'welcome.' Colorful flowers are arranged in a small vase alongside cooking utensils housed in a patterned container, creating a warm and inviting scene.

Home in Cowlesville

4.86 out of 5 average rating, 94 reviews

4-bedroom 1800s farmhouse with vintage charm

Not too far out, but enough to get that country feel! This old home has lots of charm and character. Close to many wedding venues, golf courses and only 15 minutes from Darien Lake. This home also offers a large backyard with a firepit and a few decks to choose from to sit and relax on.