Hotel holiday rentals in Windham County

Find and book unique hotel rentals on Airbnb

Top-rated hotel rentals in Windham County

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

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Superhost

Hotel room in Dover

5 out of 5 average rating, 7 reviews

Luxury King Suite w/balcony in Historic Inn, rm 1

Deluxe King Suite with balcony and living room inside of our newly renovated historic Inn. King bed and a queen pullout sofa. This unit has 1 full bath with double sinks and 1 half bath. Room comes with towels, toilet paper, shampoo, conditioner, body lotion and other toiletries. The expansive balcony has a bistro set for enjoying a coffee or happy hour. This unit also has a mini fridge and Keurig coffee maker. We provide K-cups, tea, sugars and various snacks. Inn room 1 is not pet friendly.

Guest favourite

Hotel room in Wilmington

5 out of 5 average rating, 8 reviews

Brook Bound Inn-Main Lodge-King Room 201-2nd Floor

Now Under New Ownership! Just down the road from Dover Vermont and the historic town of Wilmington Vermont, the Brook Bound Inn is 32 acres located along the Cold Brook Stream. The Inn consists of the Main Lodge, Rustic Cabin, and Carriage House. Our accommodations include a number of large rooms and suites. Located minutes from Downtown Dover, the Hermitage Ski resort, Haystack Golf club, and Mt. Snow ski resort. The property offers a pool, sports court, outdoor fire pit, and propane grilles.

Superhost

Hotel room in Dover

4.7 out of 5 average rating, 20 reviews

King Suite w/Deck near Mt Snow

Welcome to our King Room, where comfort meets luxury. The room features a cozy king-size bed with plush pillows and fine linens for a restful sleep. Step outside to your own private deck, perfect for enjoying fresh air and relaxation. The bathroom offers a custom-tiled shower for a soothing experience, complemented by premium bath amenities. Whether for business or leisure, our King Room provides a comfortable retreat with modern amenities and a touch of outdoor serenity for a memorable stay.

Guest favourite

Hotel room in Winhall

4.8 out of 5 average rating, 10 reviews

Bromley View Inn Suite #5

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 fire place, tons of seating, a bar and work table. 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.

Superhost

Hotel room in Town of Rockingham

Charming Vermont Studio - Leaf Peeping Stop

NO RESORT OR CLEANING FEES! Located on the 2nd floor, with a Japanese-style bed, loveseat, smart TV, and mini split, this room overlooking the river is a spacious alpine getaway. The new private bath is located in the hall, steps from the room, and features a walk-in shower clad in handmade tile and a custom vanity floating atop rocks foraged from the creek behind the inn. The bathroom, while private, is a short walk down the hallway outside of the room. Breakfast Included with your stay.

Guest favourite

Hotel room in Whitingham

4.93 out of 5 average rating, 169 reviews

The Engel House Room 3: Mt Snow/Wilmington VT Area

Escape to Vermont in this historical house located near Mount Snow, Wilmington, Brattleboro and Bennington. In Spring and Summer enjoy Harriman Reservoir or take in local historical sights, in Fall admire the breathtaking foliage, and in Winter ski Mount Snow or Stratton Mountain. And along with your private room and connected private bathroom are several guest common areas (not part of the hosts' living area). Our charming old house will perfect your trip to the green mountains of Vermont.

Hotel room in Brattleboro

New place to stay

This is a hotel

The beauty of Vermont is at the doorstep of The Covered Bridge Inn. Our family-owned hotel boasts clean, comfortable rooms with an exceptional staff that truly make you feel like part of the family. Conveniently located off I-91, just minutes from the New Hampshire border and one hour from Springfield, MA, The Covered Bridge Inn provides easy access to foliage and skiing destinations throughout the state. Minutes from downtown Brattleboro, our hotel puts you in the heart of it all.

Guest favourite

Private room in Townshend

5 out of 5 average rating, 7 reviews

Overlook at River & Rye in Jamaica, VT

River & Rye is an inn, restaurant, bar, and gathering place in the center of Jamaica's village. The inn, a renovated 1820s farmhouse, has six bedrooms with minimalist Scandinavian design, gorgeous stone and tile bathrooms, and access to beautiful views no matter the season. The inn is connected to our restaurant and bar, which offers Americana classics and crafted cocktails, and features produce, cheese, and meats from local farmers.

Guest favourite

Hotel room in Townshend

4.9 out of 5 average rating, 10 reviews

North Loft at Windham Hill Inn

Extremely private, this expansive loft room has its own private staircase and entrance on the second floor of our Barn building. Decorated in peaches and cream tones with shades of blue and gray, North Loft offers a true retreat from the everyday. Amenities include a four-poster king bed, sitting areas with a couch and winged-back chair, a brick surround gas fireplace, spacious deck, and private bath with Jacuzzi and shower.

Hotel room in Town of Rockingham

4.75 out of 5 average rating, 4 reviews

Serene 2 Bedrooms in Village Victorian

This listing is for booking both the Yellow & Blue Rooms here at Heart and Soul Airbnb, which is perfect for two couples and/or two guests wishing to have separate bedrooms. There is a private entrance into the house directing you straight to your rooms with a shared bathroom for guests all located on the second floor. Various porches outside make for additional seating areas and free on-site parking and wifi.

Top guest favourite

Private room in Jamaica

5 out of 5 average rating, 58 reviews

Corsica 2 room Suite at the Jamaicahaus

A Historical Inn with re-imagined amenities. Just 12 Minutes from Stratton; the Jamaica house is the turn key solution to your Vermont Get-a-way. Imagine all your needs met before you walk in the door. Bring your favorite food to cook and enjoy a social environment with a unique level of privacy.