Holiday rentals with breakfast in Bennington County

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Top-rated Holiday Accommodation with Breakfast in Bennington County

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Guest favourite

Chalet in Winhall

Chalet /Stratton Mountain VT /Tesla Charger/5 bdrm

Ski Chalet w/Tesla Charging! A quick 5-minute drive to Stratton Base, offering captivating views of Stratton Mountain on 8.82 acres of tranquil countryside. 5 bedrooms, 3 baths spread across multiple levels. The lower level unit is a versatile in-law setup or separate space for kids, while the wrap-around deck welcomes you to fully immerse yourself in nature. A detached 2-car garage with a Tesla Wall Charger. Don't miss this exceptional opportunity to make this prime location your next vacation!

LocationFamilyCleanliness

5.0 out of 5 average rating, 9 reviews

Home in Winhall

Stratton Mountain Chalet | Hot Tub, Game Room & EV

Escape to this spacious Stratton ski chalet, just 7 mins from Stratton Mountain Resort and mins from Bromley Mountain and Manchester. This family-friendly mountain retreat which sleeps up to 16 guests, is the perfect vacation rental for ski trips, family reunions, large group getaways, workcations, and year-round adventures. Whether you're planning a winter ski vacation, a spring hiking trip, a summer retreat, or a fall getaway, this all-season home is perfectly located for exploring Vermont.

LocationFamilyPets

4.78 out of 5 average rating, 64 reviews

The exterior of the guest house is framed by vibrant autumn foliage, showcasing shades of orange and yellow. A small lawn area is visible in front, with two red chairs positioned beside decorative planters. The front entrance features multiple black-paneled doors, evoking a rustic charm.

Tiny home in Shaftsbury

Studio style Vintage Garden Bungalow

Studio style guest house set on a 22 acre vintage Vermont farm. You be able to enjoy some of the originality of gardeners quarters together with the renovated and updated space. The bungalow consists of two rooms plus bath, a bedroom with double bed and a kitchenette/sitting area. Kitchenette is equipped with microwave, refrigerator, toaster oven,griddle and complimentary coffee, tea and coco. Out back a Vermont white marble veranda , seating and grill. Shower in bath, complimentary shampoo

ValueLocationHiking

4.53 out of 5 average rating, 148 reviews

Top Guest favourite

Farm stay in Bennington

The Farm Cottage- Quiet 1BR on Hobby Farm

Welcome to our peaceful 1-bedroom cottage on a small hobby farm, perfect for couples or solo travelers visiting the Bennington area. This cozy space is designed for rest and simplicity. Whether you're in town visiting family, exploring local trails, or just passing through for a few days, you’ll have a comfortable place to unwind and recharge. Thoughtful touches like fresh eggs from our chickens and homemade jams await you, while the cozy setup makes it easy to settle in and feel at home.

FamilyLocationCleanliness

4.98 out of 5 average rating, 265 reviews

Guest favourite

The entrance reveals a cozy room featuring a king-sized bed with a decorative quilt. A warm hue emanates from a pendant light above, illuminating a wooden table and a comfortable armchair. Natural light filters through the window, enhancing the inviting ambiance of the space.

Hotel room in Manchester

6 Bam Boo! Cozy escape in the heart of Vermont

6 Bam-Boo! is your cozy escape in the heart of Vermont just minutes to Manchester Center. Stay in the center of the action at this one-of-a-kind whimsical room w King-sized bed, a comfy armchair, a table with chairs, flat-screen TV with streaming services, a mini-fridge + freezer and coffee maker. Be sure to grab a snack or coffee / tea from the Snack Lounge, open 24 hours. Bam-Boo 6 is the perfect spot to unwind and recharge after exploring the Green Mountain State. Come stay with us!

LocationValueAmenities

4.93 out of 5 average rating, 82 reviews

Superhost

A spacious lounge area features a central fireplace surrounded by a large, U-shaped wooden seating arrangement with colorful cushions. A bar is visible in the background, along with large windows allowing natural light to fill the room. Wooden beams and stars add character to the ceiling.

Private room in Winhall

Bromley View Inn Suite #15

Welcome to the Bromley View Inn, where strangers become friends. While staying in this suite you will have access to our large lounge featuring a fireplace, tons of seating, a bar and worktable. Outdoors guests will have access to our beautiful deck with fire pits and seating looking over Bromley Mountain. Around the grounds you'll find two ponds, a scenic and walkable property with plenty of space to enjoy. We are 4 miles from Bromley Mountain and just 7 from both Manchester and Stratton.

LocationFamilyHospitality

4.83 out of 5 average rating, 12 reviews

A charming house features a front porch with rocking chairs, framed by lush green grass and blooming flower beds. An American flag is displayed prominently. Tall trees create a natural backdrop, enhancing the sense of privacy and tranquility.

Home in Manchester

Secluded VT home, close to town and skiing

Lovely, privately situated home (3 bedrooms, 2 1/2 baths, sleeps 6) with the true feeling of Vermont. Around the Property: Plenty of space for lawn games: croquet, horseshoes, badminton, catching fireflies. Golfers can take a 9-iron or wedge out to the 'long yard'. it's ninety yards to the tree line. Strolling, running hiking and biking on Three Maple Drive, one of the prettiest roads in Manchester. Our house is five minutes into town, 15 to Bromley, 20 to Stratton.

Guest favourite

A spacious living area features wooden beams and an inviting layout. Comfortable seating includes a green sofa and soft neutral armchairs surrounding a wooden coffee table. Bright patterned decor complements the vibrant green kitchen cabinetry visible in the background.

Home in Winhall

Fall Escape - Winhall - Fire-pit, Hot Tub

3 Bedroom, 3 Bathroom Hot Tub, Fire Pit - 5 minutes from Bromley Mountain - 8 minutes from Stratton Mountain - 15 minute drive to Manchester Bedroom Highlights: - Primary Bedroom: King bed with en-suite bathroom - Second Bedroom: Ideal for families, featuring twin and full bunk beds - Third Bedroom: Queen bed with en-suite bathroom Outdoor Amenities: - Relax in the private hot tub under the stars - Gather around the cozy firepit for evening conversations

LocationFamilySkiing

4.97 out of 5 average rating, 33 reviews

Top Guest favourite

A charming townhouse is set amidst vibrant autumn foliage, showcasing a classic exterior with a gabled roof and large windows. The surrounding trees display a mix of red, orange, and green leaves, creating a picturesque environment that highlights the seasonal beauty.

Townhouse in Dover

Experience Vermont's Fall Magic at the Lemondrop

Wake up to crisp mountain air and Vermont’s brilliant fall colors at Lemondrop Lodge. Our pet-friendly, 3-bedroom, 3-bath townhouse sleeps eight and puts you minutes from Mount Snow. Spend the day hiking, taking scenic drives, or exploring nearby Wilmington, then unwind by the wood-burning fireplace, gather for games in the den, or enjoy the shared heated indoor pool at the Kingswood clubhouse. It’s a cozy place to reconnect with family and friends this fall.

ValueLocationAmenities

4.99 out of 5 average rating, 76 reviews

Home in Wilmington

Chalet Lopez

Welcome to Chalet Lopez, your cozy getaway in Wilmington, Vermont. Enjoy fast WiFi, a fully equipped kitchen, comfy living spaces with propane heat, and a beautiful fireplace ready for you to relax by. You will be close to Mount Snow, hiking trails, lakes, golf, great restaurants, and local bars. House rules are simple: no pets, no smoking, no parties, quiet hours at 9pm, and please keep food out of bedrooms. Checkout is easy and quick.

FamilyLocationCleanliness

5.0 out of 5 average rating, 4 reviews

Guest favourite

A cozy sleeping area is presented with a plush bed adorned with soft blankets and decorative pillows. The space includes a built-in fireplace with stacked logs, and a star-shaped wall decoration adds a rustic touch.

Private room in Dover

Deluxe King, kitchenette,fireplace- Cider House 1

This high-end studio at Farm Road Estate has a luxury king bed and sitting area, a kitchenette with cooktop, refrigerator, Keurig coffee maker (we provide k-cups, sugars, and creamers), microwave, and toaster. The living room has a 65 inch 4K Roku TV. This unit has 2 sinks in the bathroom, a full tub and separate shower. Toilet is in a private room. Cider House 1 has a private patio and parking area. Cider House 1 not pet friendly.

LocationValueAccess

4.97 out of 5 average rating, 39 reviews

Top Guest favourite

The historic two-story house features a blue exterior complemented by a white porch adorned with hanging flower baskets. A pathway lined with greenery leads to the entrance, enhancing the inviting appearance of the home surrounded by mature trees.

Guest suite in Dorset

Guest Suite in historic 1804 tavern, w/ Breakfast.

You'll have the whole 3rd floor to yourself with a new private bath, large bedroom with a/c, and a separate sitting room/library. Stay in an historic gem, listed on the National Register of Historic Places. Historically sensitive restoration has been done. You'll have a continental breakfast in the house's original dining room. We're a four a minute drive from the center of historic Dorset village.

LocationValueTV

4.91 out of 5 average rating, 222 reviews