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Holiday rentals in Wallingford

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Top-rated holiday rentals in Wallingford

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

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Guest favourite
The exterior of a red wooden house is showcased, surrounded by lush green grass and trees. A neatly trimmed garden features colorful flowers, while a small shed is visible in the background. Pebbled pathways provide access to the home's entrance.
Flat in Mount Tabor
4.93 out of 5 average rating, 122 reviews

Vermont Ski/Okemo/Killington/Pico/Stratton/Bromley

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.

Top guest favourite
A vintage gas station building features a white exterior with red lettering spelling 'TEXACO.' Large glass windows line the front, showcasing a clear view of the interior. The American flag is displayed prominently, and a tree-lined background adds a touch of greenery.
Home in Castleton
4.94 out of 5 average rating, 137 reviews

Cozy Contemporary Downtown Texaco

Stay with us if you’d like to be in the center of downtown Castleton. Stores, restaurants, the college and hike/bike rail trail are an easy walk. This is a very convenient location. We are also a short 30-40 minute drive to Pico and Killington ski areas. Five minutes to Lake Bomoseen. Recently updated, heat and AC, full bath, Wi-Fi, Qled tv, a comfortable king sized memory foam bed, a complete kitchenette. Reserved parking adjacent to entry. Everything you need for an overnight or longer stay

Top guest favourite
A cozy seating area is presented, featuring a patterned rug beneath a wooden coffee table. A sofa with light-colored cushions and decorative pillows is accompanied by a lamp providing warm light. A chest of drawers and a framed artwork add character to the inviting space.
Flat in Wallingford
5 out of 5 average rating, 104 reviews

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.

Top guest favourite
An old barn features weathered wooden siding and large windows, set against a backdrop of vibrant autumn foliage. A maple tree with bright orange leaves provides a natural canopy, while a carpet of fallen leaves covers the grassy ground, creating a serene outdoor scene.
Barn in Mount Holly
4.81 out of 5 average rating, 159 reviews

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.

Top guest favourite
The historic Italianate home features a white exterior, with classic green shutters adorning tall windows. A spacious porch is supported by graceful columns, providing numerous seating options. The surrounding yard displays mature trees, enhancing the charm of the property set against a serene backdrop.
Flat in Middletown Springs
4.9 out of 5 average rating, 278 reviews

Apartment in Vermont Historic Home

This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

Top guest favourite
A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.
Barn in Chester
4.99 out of 5 average rating, 724 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

Top guest favourite
A spacious living room features a comfortable sofa and armchair, enhancing relaxation. A large television is positioned in front, with decorative elements and artwork on the walls. Soft lighting from lamps and windows creates a welcoming ambiance in the well-designed space.
Guest suite in Clarendon
4.95 out of 5 average rating, 203 reviews

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

Top guest favourite
Home in Clarendon
4.95 out of 5 average rating, 320 reviews

Killington Retreat | Deck-Fire Pit-Mountain Views!

Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

Top guest favourite
A cozy cabin is surrounded by a serene winter landscape, with snow-covered trees enveloping the property. The structure features a sloped roof and multiple windows, while a snow-dusted pathway leads to the entrance. A propane tank is positioned beside the cabin for convenience.
Cabin in Mount Holly
4.97 out of 5 average rating, 262 reviews

Private Cabin/PetsOK/Minutes to Okemo/Fast Wifi

Enjoy the beauty of Vermont at our private cabin. Situated on acres of woods next to a small creek, the cabin is 15 minutes to Okemo Mountain and scenic Vermont towns for dining and shopping. With a queen bed loft, a double bed bedroom and a pull out sofa, the cabin sleeps up to 4 people. The kitchen is nicely equipped and there is a charcoal grill outside. High speed fiber optic internet will keep you connected. Max 2 pets allowed.

Top guest favourite
A view of the snow-covered path leading to the ski slopes is framed by the C Building’s balconies. Sunlight casts long shadows across the pristine snow, highlighting the tranquil winter scene. The surrounding area is clear and inviting, with ski signage visible in the distance.
Apartment in Ludlow
4.93 out of 5 average rating, 162 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Top guest favourite
The exterior of a traditional white house features a spacious covered porch lined with wooden railings and supported by columns. Potted plants and hanging baskets add greenery, while the entrance is framed by multiple windows. A gravel driveway leads up to the porch.
Flat in Rutland
4.96 out of 5 average rating, 656 reviews

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, skiing, golf, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

Top guest favourite
Flat in Poultney
4.94 out of 5 average rating, 379 reviews

Cozy Poultney Village Apartment

I enjoy booking my two-story in-law apartment with a private entrance, which is attached to my 1850 Poultney Village home. I am located a block from Main Street with shops, books, and eateries. I am in the lakes region of Vermont, close to both Lake St. Catherine and Lake Bomoseen. Killington is 35 miles away. We am also located a mile from the NY border and the entrance to Lake George and the Adirondacks.

Popular amenities for Wallingford holiday rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Rutland County
  5. Wallingford