Holiday houses in Whitingham

Guesthouse in Marlboro Township

4.97 out of 5 average rating, 160 reviews

Refined, serene and like no other, Marlboro, VT.

Our elegant, supremely comfortable, and private guesthouse is surrounded by a wonderful garden and 350 acres of woodland in the quiet of rural Vermont. We are 30 minutes from Brattleboro to the east, with its many shops and restaurants, and 12 minutes from the small town of Wilmington to our west, with some restaurants, shops, and a supermarket However, we always recommend bringing groceries, etc., for your first night and next morning. We are pleased to offer a 20% discount for 7 days or more!

4.9 out of 5 average rating, 221 reviews

Wilmington A-Frame- Cozy and Convenient

Entire charming and chic A-frame chalet conveniently located to all the amenities Wilmington has to offer. Walk into town to enjoy dining, shopping and trail hiking or take a short 15 minute drive to Mount Snow for a day of outdoor adventure. Relax on the water at Harriman Reservoir, just a 2 mile drive from the house. House is also conveniently located along the Moover route. Relax back at the house while enjoying time on the front porch or an evening on the couch. Located on Main Street.

4.99 out of 5 average rating, 207 reviews

Vermont Sugar House Retreat

Stay at this unique rustic Vermont getaway. Nestled on a quiet hill in Wilmington, this private retreat will serve as the perfect home base for your Vermont adventures. You'll have the house to yourself without a neighbor in sight. While very private and surrounded by beautiful forest, this house is still only a short 5 minute drive from downtown Wilmington. The house is built around an enormous one-of-a-kind natural stone fireplace that was formed atop the old foundations of a sugar house.

4.91 out of 5 average rating, 106 reviews

Tiny home in Whitingham

Cozy Lakeside Tiny Home, Near Skiing

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store, located 5 minutes away, will make you fresh egg sandwiches, pastries, and coffee. For lunch, come in and get fresh made subs or our famous brick oven pizza slices. A perfect getaway for couples, friends, or family in every season. Enjoy kayaking, fishing, ice skating and boating on serene Sadawga Lake. It's a quick drive to skiing at Mount Snow, shopping and dining in Wilmington, and direct access to the VAST trail.

4.99 out of 5 average rating, 275 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

4.9 out of 5 average rating, 102 reviews

Home in Whitingham

Vermont lake house near Mt. Snow-fab 360 views!

Welcome to our fab farmhouse on 3 green acres! Enjoy amazing views of Lake Sadawga and the surrounding Green Mountains as you kick back in our cozy and stylishly furnished home. The house comfortably sleeps 8+ with 4 bedrooms, 2 full bathrooms and a finished loft space. The house is located off the beaten path on a paved road with multi-car parking. We are a short drive to skiing at Mt. Snow, boating in Harriman Reservoir, and near lots of local amenities. A wonderful year-round retreat!

4.93 out of 5 average rating, 139 reviews

Campervan/RV in Guilford

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

Barn in Marlboro Township

4.96 out of 5 average rating, 315 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

4.99 out of 5 average rating, 107 reviews

Cabin in Whitingham

Cozy Cabin ~16 Mi. to Slopes on 10 Acres of Woods!

Tucked away in the bends of Burrington Hill Road, you’ll find our family’s Whitingham Wonderland, where our Irish touch is sure to make you feel at home and our NYC energy will keep you entertained. Our home is stocked with games for all ages as well as multiple Smart TVs, a fire pit and grill. To enjoy all Vermont has to offer we are only 30 minutes from Mt Snow and 45 from Stratton with the towns of Wilmington & Dover peppered along the way. Come make memories to last a lifetime!

4.97 out of 5 average rating, 118 reviews

Cabin in Whitingham

The Hideaway Camp

The Hideaway Camp is a very private cabin on a 100 acre property. There are hiking/x country ski trails on the property and close access to the VAST trails. A scenic 20 acre pond for kayack and canoeing and a brook with a rustic cocktail deck overlooking it. the Jacksonville General store is 2 minutes away and it is warm and friendly with all the groceries you might need. The cabin is well stocked for cooking and with high speed internet you can WFH or stream favorite shows.

4.86 out of 5 average rating, 133 reviews

Cottage in Monroe

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

Guest suite in Wilmington

4.92 out of 5 average rating, 774 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Whitingham holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Whitingham

Superhost

Cabin in Stamford

4.89 out of 5 average rating, 9 reviews

La Cabañita - The Little Cabin

JulissaRating, 5 stars1 month ago

Nick’s place is amazing—just a little peace of heaven on earth. The cabin and surroundings are so peaceful and beautiful and it felt very private. Our favorite part of the cabin were the screened in porch, the swing, and the fire pit. Nick was very generous and provided lots of fire wood for our stay and even had the fire pit ready for us when we arrived. Our boys also loved running around the cabin. We had everything we needed during our stay. We will definitely be back!

4.96 out of 5 average rating, 49 reviews

Vermont Village Retreat Near Mount Snow

TRating, 5 stars1 month ago

Matt's Airbnb was a wonderful place for us to get away for a long weekend! The house was lovely with all the comforts of home. We loved so much about this house, especially the layout. All one floor, which was great! The mudroom was great for bags and boots, the kitchen was well stocked , and the living room was amazing- very comfy large sectional sofa for relaxing, a nice cozy little sun room to hang out on and read a book. Having 3 bedrooms and 2 baths were the perfect size, and the washer and dryer were an added bonus. We loved the outdoor space for grilling and walking our pups. Very peaceful neighborhood and wonderful little town with great restaurants! Matt was so nice and helpful with any questions that we had, and even offered us a later check out which was nice! We loved this part of VT and hope to visit again soon! Thank you Matt for being such a great host! We can't wait to book our next stay!

5 out of 5 average rating, 36 reviews

Guesthouse in Wilmington

Cozy, charming cottage 7 mins from Mount Snow

DanielRating, 5 stars1 week ago

Gracious host and always quick to respond (within minutes!)

5 out of 5 average rating, 18 reviews

Cabin in Wilmington

Cozy Mountain Retreat - near Mt Snow

DominicRating, 5 stars3 months ago

Simply a great and cozy place. Perfect for a quiet long weekend in the mountains. You can tell the hosts put a lot of thoughts into the place. They are lovely people and very helpful. Highly recommend booking!

4.96 out of 5 average rating, 27 reviews

Family/Dog Friendly Mountain Home w/ Amenities

ReutRating, 5 stars2 weeks ago

The house was just outstanding!! Beyond our expectations. We had so much fun at the house with such great facilities and wonderful location.

5 out of 5 average rating, 30 reviews

Rustic home near skiing & lakes, walk to downtown

KassRating, 5 stars2 weeks ago

Very welcoming home, amenities were a great way to entertain ourselves during the night while kids were sleeping. The spacious living room, dining room and kitchen were an absolute dream! Would stay here again!

Superhost

Home in Dover

4.91 out of 5 average rating, 82 reviews

FULLY renovated 1 bed/1 bath ski in-out condo!

AnastasiaRating, 5 stars2 months ago

My husband and I spent a long last winter weekend here. The condo was perfect for ski on/off and we enjoyed a day on the mountain. Though the weather wasn’t great the whole time, Brittany & Jen were quick to send recommendations for things to do, trails to hike and their favorite restaurants. So close to lots of great spots in this little mountain town. We would absolutely stay here again