Windham County

Boutique Hotels in Windham County

Select your dates to find the best Windham County Boutique hotel deals

Scroll down to see hotels
Filter by:
Hotel Star Rating
≤2345
Guest Rating
Amazing 9+Great 8+Good 7+Pleasant 6+

Top Boutique Hotels in Windham County

Check out our pick of great boutique hotels for your travel
Most Booked
Lowest price
Closest to downtown
Highest Rated
84
Hotels in Windham County
Featured facilities: Swimming Pool
Very Good
21 reviews
8.2/10
1 night
From €160
Check Availability
44
Hotels in Windham County
Featured facilities: Swimming Pool
Outstanding
3 reviews
10/10
Check Availability
46
Hotels in Windham County
Located in West Dover, The Hermitage Inn Vermont is in the mountains, within a 10-minute drive of The Hermitage Club and The Hermitage Golf Club. This golf inn is 3 mi (4.8 km) from Mount Snow and 4.3 mi (6.9 km) from Mount Snow Golf Course. Dip into one of the 2 hot tubs or enjoy other recreational amenities including a sauna and a 24-hour fitness center. Additional amenities at this inn include complimentary wireless internet access and concierge services. Enjoy a satisfying meal at Tavern serving guests of The Hermitage Inn Vermont. Quench your thirst with your favorite drink at the bar/lounge. A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM. Featured amenities include express check-out, luggage storage, and a library. Free self parking is available onsite. Make yourself at home in one of the 14 air-conditioned rooms featuring fireplaces. Your bed comes with down comforters and Frette Italian sheets. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms have jetted bathtubs and designer toiletries.
Very Good
7 reviews
8.6/10
1 night
From €277
Check Availability
46
Hotels in Windham County
Located in Brattleboro, Inn on Putney Road is on the waterfront, a 5-minute walk from Brattleboro Common and 8 minutes by foot from Connecticut River. This bed & breakfast is 0.5 mi (0.9 km) from The Stone Church and 2.3 mi (3.7 km) from Brattleboro Farmers' Market. Pamper yourself with onsite massages or take in the view from a terrace and a garden. This bed & breakfast also features complimentary wireless internet access, concierge services, and gift shops/newsstands. Quench your thirst with your favorite drink at the bar/lounge. A complimentary full breakfast is served daily from 8 AM to 9:30 AM. Featured amenities include a 24-hour business center, express check-out, and luggage storage. A train station pick-up service is provided at no charge, and free self parking is available onsite. Make yourself at home in one of the 6 individually decorated guestrooms, featuring refrigerators and DVD players. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include desks and complimentary bottled water, and housekeeping is provided daily.
Outstanding
56 reviews
9.8/10
1 night
From €244
Check Availability
30
Hotels in Windham County
Nestled in the forest just 7 minutes to Mt Snow and 15 minutes to Stratton, this charming cabin seamlessly blends comfort and convenience. Perfectly situated for outdoor enthusiasts, you'll have easy access to hiking, biking, and fly fishing adventures. The cabin boasts ample windows, vaulted ceilings, and wood floors, creating a bright and airy open-concept space ideal for relaxation and entertaining. Unwind on the plush sofas for a cozy movie night or curl up by the fireplace with a good book!The house has 4 bedrooms, 2 full baths, 2 living room areas, full kitchen, deck with seating and grill, fire pit, fireplace in living room and a game area downstairs.For added fun, a selection of board games is available for game nights. A second living area offers another cozy spot for movie watching, while a loft provides extra sleeping space. Step outside to the deck for fresh air and serene mountain views, and gather around the firepit to stargaze and plan tomorrow’s adventures. Additional perks include free high-speed WiFi and a private washer/dryer.Things to Know:Check-in time: 4:00 PMCheck-out time: 11:00 AMQuiet hours are from 10:00 PM to 8:00 AM.No smoking is permitted anywhere on the premises.Firewood is provided.4WD is required during winter months and mud season.This property does not have air conditioning.Parking Notes: Free parking is available for up to 3 vehicles.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Outstanding
10/10
Check Availability
47
Hotels in Windham County
Welcome to The MountainTop in Stratton! Located 10 minutes north of Mt. Snow and 15 minutes south of Stratton Village. The home is centrally located near numerous hiking trails, breweries, restaurants and all things Vermont. The home is quiet and private with night time views of the stars like no other.About pets:No pets allowed.About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.
Outstanding
10/10
Check Availability
51
Hotels in Windham County
The River Shack is a quintessential cozy cabin in the quiet woods of Southern Vermont. The property is surrounded by wildlife & nature! Find yourself relaxing to the calming sounds of the West River just steps away from the back porch. The River Shack features A small sandy beach and 100 feet of sparkling river view. The water is crystal clear - perfect for a dip, snorkel, cast a fishing line or a lazy tube ride down river. You’ll find endless activities including hiking, waterfalls, swimming, golf courses, skiing, fishing and ATV rentals from your local outfit. Take a scenic drive to 3 ski mountains within 30 miles (Stratton 30 miles, Bromley 25 miles, Mount snow 16 miles). Brattleboro ski hill is a few miles away (great for the kiddos). Okemo ski mountain is 47 miles about a 1 hour drive & Magic Mountain is 28 miles- 40 minutes away.. take a little road trip through the mountains 😊The River Shack is a wonderful year round retreat! Downtown Brattleboro is just 5 miles away. Here you will find an array of restaurants, movie theatre, bars, and shops! Inside The Shack the kitchen is equipped with all the amenities of home including stainless steel refrigerator & microwave, dishwasher, toaster oven, coffee pot and tea kettle. There is a dining area that seats 4-6 people two steps down from an open concept living room. Plus a gorgeous view of the river!The Kitchen is supplied with: cookware, pots, pans, plates, cups, bakeware, wine glasses and silverware. Additionally there is a coffee machine, a cold brew maker, and lots of other items to make your time here as convenient as possible. Ground coffee & tea is provided!The living room has a sofa with an ottoman and extra blankets inside. There is a rocking recliner a side chair with ottoman and two Japanese floor mats rolled up to the side to maximize this cozy space. This is a small space, Please note the minimal seating. We provide extra folding chairs in the laundry room of extra seating is needed. There is also a 50 inch smart TV with surround sound, Bluetooth/WiFi equipped. Fresh linens, towels, body wash, shampoo & conditioner are also provided! Outside there is a walk out deck from the kitchen sliding doors with a bistro patio dining table and an outdoor grill. Sit relax and watch the river flow by. Or play some yard games, there is plenty of space. There is also a riverside fire pit for s’more roasting and quality time. A driveway with 2 parking spacesThe Cabin is suitable for 4 adults please be aware of the sleeping accommodations when booking for 4 adults. We can accommodate a 5th adult with our air mattress. Please See the bed layout and bedroom information. For families, the cabin is suitable for 2 adults and 3 children. Bedroom 1: queen bed with a large closet space (queen air mattress & extra linens and blankets in the closet) Bedroom 2: A bunk bed with 1 full and 1 twin bed and a twin trundle underneath. A corner Rocking chair & a variety of games & puzzles!Common area which would be the living room- has enough room for the queen size air mattress you’ll find in the master closet in there you’ll also find Extra linens and pillows. There is a locker in the living room for coats & shoes. Also, there is an electric fireplace under the TV. Laundry room is off of the living with equipped with a washer & dryer. Kayaks, helmets & life vests provided for guest use! You can find them in the storage shack next to the river. There you’ll find lounge chairs, umbrellas, yard games, beach toys, etc! Please note, if you like off the beaten path authentic experiences, this is your place! This is by no means luxury. It’s a little cabin in the middle of the woods!We hope to host you at the River Shack!About pets:Pets allowed: dogs (limit 2 total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:No glass bottles by the river.No noise outdoors past 10pm, be mindful of ours neighbors.,No shoes indoors due to out dirt road, it gets muddy...About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
13 reviews
10/10
Check Availability
17
Hotels in Windham County
Located in Long Trail House directly across the street from Stratton Village and main base lodge, this beautifully renovated top floor condo offers 2 bedrooms and 2 full baths on two separate floors. Enjoy all the amenities our condo has to offer including year round heated outdoor pool and hot tubs, a communal sauna, concierge, heated covered parking, washer/dryer on floor, and ski lockers to store your gear. Conveniently located - walk right across the street to Stratton village for the great restaurants, shops, rentals and ski lifts. Enjoy views of the skating pond from the outdoor balcony, or relax by the gas fireplace after a day of activities. Fully stocked kitchen makes meals a breeze. Coffee provided mornings in lobby.The two well situated bedrooms (one queen primary with full bath, and one bunk room with a twin upper/full lower bunk + extra twin) and sleeper sofa in living room allow comfort for all different groups - perfect for families, small friend group, or a few couples. About pets:No pets allowed.About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.
Outstanding
19 reviews
9.8/10
Check Availability
21
Hotels in Windham County
Enjoy the entire house of 2200 sq ft. This two floor chalet is located on two private wooded acres just 6 miles from Mount Snow Resort. Only a short drive to skiing and snowboarding. The historic town of Wilmington is 5 miles south providing many restaurants, shopping, groceries, and local artist’s studios. Stop at Valley Craft Ales or buy local maple syrup. Very fast fiber optic WiFi-300mbps. Plus filtered water through the entire house (5 micron/KDF/Carbon).The house is very family friendly with lots of games to choose from, a 55” tv with Netflix, Disney+, Prime, Apple TV, Peacock, and Hulu ready to watch. A 7’ air hockey table provides for additional entertainment in a separate building. A high chair, pack and play, kids stool, and a bin of toys are all available for the kids.Sleep comfortably in three bedrooms with queen memory foam mattresses, and twin bunk beds. The house has privacy for 8 people. There is separate heat control in all three bedrooms. All bedding, pillows, and sheets are provided and all the beds are made prior to arrival. Lots of amenities included to provide the feel of home. On the 2nd floor there is a large dining table for 8, a galley kitchen with fridge, breakfast counter, microwave, coffe maker, toaster, electric stove and oven. Soft leather furniture provides lots of seating upstairs to relax by the vented propane fireplace. Enjoy the quiet of Vermont, read, or play music and relax with many games to choose from. The 2nd floor bath has multiple shower nozels to provide full body spray. Dont forget to flip the Instant hot air heater on to avoid any chills during the winter.This house has very specific cleaning and disinfecting procedures to provide a very clean home for all guests. The Outdoor fire pit with dried wood is provided. Pick a color Adirondack chairs. Both firepit and chairs are available available from May thru October.The gravel mountain road and inclined gravel driveway requires 4WD/AWD in the winter and spring mud season. (November-April)The parking area in front of the house is well lit at night with motion lights and space for 4+ vehicles on level ground. Enjoy all year in Vermont!About pets:No pets allowed.About checkOut:Check out before 2:00 PM.About children:Children allowed: ages 0-17.Childrens toys, games, gate, safety rail in closet.About customRules:Please be respectful of the no smoking and no animal policy. Our kids are very allergic . Thank you..No ski boots, boots, and shoes past the mud room please. Thx,Please remember that 4WD or AWD is required from November-April..About checkIn:Check in after 9:30 AM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 23.About events:No events allowed.
Outstanding
18 reviews
10/10
Check Availability
15
Hotels in Windham County
Featured facilities: Swimming Pool
Amazing
21 reviews
9.4/10
Check Availability
See All Boutique Hotels in Windham County

Frequently Asked Questions

How do I book a hotel on Trip.com?

To book a hotel on Trip.com, simply enter your destination, travel dates, and the number of guests on the page. Then, browse through the available hotels and select the one you want to book. Follow the prompts to enter your payment information and complete the booking.

How do I get hotel deals on Trip.com?

There are several ways to find affordable hotels on Trip.com. You can narrow down your search results by filtering hotels according to your preferred price range, or you can sort the results by price to view the cheapest options first.

Where can I find hotel deals on Trip.com?

Trip.com offers a wide variety of hotel deals and promotions that are available throughout the year. You can easily find these special offers on our deals page. What's more, if you are a member of our loyalty program, you can sign in to your account and discover exclusive discounted rates at hotel list pages.

How can I get lower prices for hotels?

Sometimes booking hotels midweek is cheaper, but it also depends on the season.

How many hotels are listed on Trip.com?

You’ll find over 1,500,000 hotels in 230+ countries and regions on Trip.com. Can’t decide which hotel to book? Browse the site for inspiration!

Can I cancel or change my hotel bookings on Trip.com?

It depends on the hotel policy and date of cancellation. Please check the policy section of the related hotel pages. To cancel or change your bookings, sign in to your Trip.com account, go to "My Bookings", and follow the instructions.

How do I contact Trip.com customer support?

You can contact Trip.com's 24/7 customer support by visiting the Help Center on Trip.com and submitting a request. You can also contact us by phone or service chat, depending on your location.