Vacation rentals in Wallingford

Elegant Alpine Condo - Golf, Bike & Pool!

Stylishly updated 1-bedroom Whiffletree condo with an upscale alpine feel—minutes from Killington Resort, golf course, and access road. Thoughtfully stocked with essentials, plus a private gear locker for convenience. Unwind at the onsite outdoor pool (open Memorial Day–Labor Day) or explore nearby hiking, biking, and Vermont’s scenic beauty. Comfortably sleeps 4 with a king bed and queen pullout sofa. Pack & Play crib, mattress and sheets available upon request for $25 per stay. Reg #007718

Green Mountains of Vermont/ 20 Min to Manchester

We welcome you to come experience Vt. We are a quiet, private, cozy, clean, stay in the country. Located equal distances to all surrounding towns and ski areas. Drive the Green Mountain National Forest road #10 to Peru, Landgrove & Weston. Hike on the Appalachian and Long trail. Fish, bike, forage, swim and spelunk (caving) Dine & shop, Manchester, East Dorset, Wallingford & Rutland. Walk around Danby. Take a scenic drive to Pawlet & Dorset. Ski, Killington, Pico, Okemo, Bromley, Stratton.

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!

49 River Street

Here, you'll enjoy a fantastic getaway surrounded by numerous activities. Just off Rt. 7, alongside the Otter Creek. Close to local ski areas Killington, Okemo, and Stratton Mtns., as well as hiking on the Long Trail and White Rocks Rec. Area. Ideal for a trip, solo or with a small family. Inside, you'll find a comfortable queen-size bed, and a pull-out couch. The kitchen is ready for cooking. Plus, you'll be in walking distance to charming village shops, convenient stores, and a playground.

Waterfront Vermont Lake House w/ Panoramic Sauna

We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from either our private decks. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

Out On a Limb • A Magical Treehouse Experience

Welcome to Out on a Limb, our magical treehouse nestled in the serene woods of upstate New York. This cozy, charming hideaway offers a peaceful & romantic escape, perfect for couples or solo travelers looking to connect with nature. Surrounded by towering trees, the treehouse provides a unique experience year round—from relaxing in the hot-tub on a snowy night, to stargazing by the campfire. The treehouse is always stocked with waffle mix & homemade frozen cookies. We can’t wait to host you!

Mapleside Escape: Sugar/Ski house

Your Mapleside Rustic Retreat awaits! This gem is nestled amidst the picturesque landscapes of southern Vermont and only a 12 minute drive to Okemo/Jackson Gore, 35 minutes to Killington/Pico. If the season is right it offers the unique opportunity to see some pure VT maple syrup being made! Skiing, snowboarding, hiking and mountain biking trails await, making this spot an ideal base for year-round fun. Come explore nearby towns which offer charming shops, dining, and cultural experiences.

Cow Barn Lodge

Our home is located in MT. Tabor, Vermont, just off of Route 7, in a country setting with beautiful Mountain views of the Green Mountain National Forest, Dorset and Danby Mountains. The house is an old barn converted into a beautiful spacious home, on 4 acres. Snowmobiling from our place, plus 4 major ski areas less than 30 miles away. Hiking, fishing, swimming, golfing, and the Equestrian horse show are all nearby. as well as shopping in nearby Manchester and Rutland Vermont.

River House Apartment - Dog friendly

Entire downstairs of a house with one double bed. There is nice bathroom with shower. There is a microwave, coffee, massage chair, outdoor grill and picnic table. Internet and cable provided with fire stick for the TV. Fire pit and hot tub are shared by other guests. Up to three and all size dogs or pets are allowed and welcome. The three acres has a lovely place for them to run and has been sprayed for ticks and mosquitos. Please note: key replacement $30 if lost or taken

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

Kingsley Grist Mill Waterfall & Private Beach OMG

One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.