Holiday rentals with breakfast in Bennington County

Spring Escape Near Hiking, Golf & Mount Snow

Wake up 5 minutes from Mt Snow at Lemondrop Lodge, a whimsical 3BR / 3BA townhouse. Perfect for ski weekends, family snow days, and winter getaways, our home puts you close to the lifts, trails, and all the action. Spend your days skiing and snowboarding, tubing, or exploring the Green Mountain National Forest. Come home to a warm, inviting space with plenty of room to spread out, cook and relax after a day on the mountain. Perfect for a romantic getaway, a family adventure, or a restful escape.

Stratton Mountain Getaway: Hot Tub, Firepit & Pond

Welcome to your perfect Vermont getaway! This spacious chalet in Strattonwald is ideal for late-season skiing, spring hiking and outdoor adventures. Just minutes from Stratton Mountain Resort, Bromley’s slopes, Manchester’s shops & dining, and scenic Mountain trails, it’s the perfect base for families or small groups. Whether you’re building snowmen with the kids, cozying up by the fire, soaking in the hot tub, hiking, or kayaking in the nearby pond, this home balances adventure and relaxation.

E and E’s B and B Queen Bed Rm+ Pool & Hot Tub

We are located on 16 East Street in Bennington VT minutes from rt 7 and route 9 Main Street. Summer is more like a mini resort with a beautiful in-ground pool and Hot Tub. We also feature plenty of in-room USB phone plug-ins and extensions, in room TVs.. Perfect for couples or bring a child. Sunning Deck or shaded patio dining or just relaxing with a good book poolside or the indoor lounge with a drink. We’ve got you covered. Many unexpected amenities. Longer stays allowed for professionals.

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

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!

The Farm Cottage

Take a break and unwind at this little peaceful oasis. A little bit of the country is right beside you with the neighing horses and clucking chickens who roam our property. We are close to Bennington College, great restaurants and Robert Frost house. We are 35 minutes from Manchester where you’ll find terrific outlet shopping and a variety of restaurants. Bromley Mountain is just beyond Manchester in Peru, Vt. It is a year around resort with water slides in summer and skiing in winter .

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.

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

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.

Tucked Away, cozy space and an easy walk to town

Tucked Away is a newly renovated two-bedroom cottage with all the charm of old Vermont and outfitted with modern touches to make your stay as luxurious as possible. Set in downtown Manchester, Tucked Away is set back off the main road, giving it a more private feel. There is space in a shared driveway for two cars to park, and the house is walkable to almost anything you could want to access in Manchester.

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.

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.