
Holiday houses in Proctor
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Top-rated holiday rentals in Proctor
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Home Sweet Grove Street
Enormous 4 bedroom/1 bathroom apartment. 2000 sq ft.. Second floor. Entrance in front of the house. Parking in rear. Large dining room, living room and kitchen. Covered porch off of kitchen to enjoy some time outside. Tons of natural light. Perfect for large families or groups of friends. Dining room table seats 10+. House is one block from downtown. Walk to the restaurants, bars, movie theater, grocery store, bus depot, train depot,Walmart. Convenience store 3 houses down. Skiing 20 mins away.
FamilyLocationIndoor spaces
4.88 out of 5 average rating, 285 reviews
Mountain Getaway Pet friendly
Escape to our charming getaway, ideally located in Rutland just 20 minutes from the world-famous Killington Ski Resort! Whether you're here for skiing, snowboarding, hiking, or simply enjoying the serene beauty of Vermont, our home offers the perfect base for all your adventures. Our home offers a cozy and welcoming environment, perfect for families, couples, and groups of friends. You'll love the combination of comfort, convenience, and proximity to the best of Killington's outdoor adventures.
LocationFamilyGetting around
4.94 out of 5 average rating, 125 reviews
Mountain View Apartment
Quiet, second floor, farmhouse apartment in country setting. Two connected bedrooms sleep four, one with a queen bed and the other with two twin beds. Watch the sunrise from the private deck or walk the fields to watch the sun set over the Adirondaks. Plenty of room to roam over the farm fields. Owner on property. 15 minutes from Castleton University. Please see more under "your property" -18 mi to Killington Resort/ 15 mi to Pico Ski Resort -9 miles to Rutland Regional Medical Center
LocationValueAir conditioning
4.92 out of 5 average rating, 142 reviews
Waterfront cottage walk-out suite.
Private entrance suite overlooking Burr Pond. Conveniently close to Mountain Top Inn & Resort (3.7 miles), Killington/Pico ski resorts and Rutland. Swim, kayak, bike and hike. Take advantage of more than 12 miles of the Pittsford Trail Network. The serenity of country living coupled with the amenities of Rutland! We’re on a short dirt road off of a steep hill. Front or 4 wheel drive vehicles with good all season or snow tires required in the winter. Not suitable for toddlers or children.
FamilyLocationBreakfast
4.99 out of 5 average rating, 166 reviews
Waterfront Vermont Lake House w/ Panoramic Sauna
Waterfront on Lake St. Catherine, with almost 100ft of private lake frontage and a view that's hard to beat. Watch the sunrise from the deck or from inside our new panoramic barrel sauna. Explore the lake by kayak or canoe — both included for guests. Keep an eye out for both bald eagles and loons. There's also a fire pit for evening s'mores — firewood included as well. Great for families — we've got a crib, a bunk room for the kids, and a bookshelf of board games for those rainy days.
FamilyValueAccuracy
4.93 out of 5 average rating, 408 reviews
Kingsley Homestead - walking distance to Downtown
Come stay in our quiet and relaxing two bedroom suite. We accommodate 4 people comfortably. We are very close to Rutland Golf ⛳️ , Pine Hill Park, Killington. Walking distance from downtown. There is a queen bedroom with a equipped kitchenette, large living room, and bath with shower and a whirlpool tub to relax in after a long day of outdoor adventures. There is a second bedroom that has two twin beds. Many small appliances. No stove. There is a two-burner portable stove.
FamilyLocationAccess
4.98 out of 5 average rating, 163 reviews
Peaceful Pond View ~30 mins to Killington
Relax with the whole family while taking in beautiful views of this peaceful pond. Kayak, fish and swim in the warmer months, or hit the slopes in the snow. There are also a few hiking trails within walking distance. Close to many restaurants and only half an hour away from Killington/Pico. Close to Chittenden, Lake Bomoseen & Lake George. Enjoy the quiet and get cozy while relaxing and spending quality time with each other. Small dogs considered, but must get owner approval.
FamilyLocationKitchen
4.98 out of 5 average rating, 61 reviews
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.
LocationValueHospitality
4.98 out of 5 average rating, 520 reviews
Red Rooster Fall Foliage Hub Near Downtown Rutland
Welcome to The Red Rooster, a private second-floor guest suite in a historic 1867 Greek Revival Victorian with ample parking. Located on urban micro-farm, tucked into Rutland's Historic District, enjoy peaceful views and perfect urban convenience. Walk right to downtown dining, Amtrak, and the Paramount Theater! We are minutes from Killington Resort, Pico, the VAST trail, Appalachian Trail, and Lake Bomoseen. Your Green Mountain basecamp awaits.
FamilyValueOutdoor spaces
4.94 out of 5 average rating, 116 reviews
Adorable townhouse in Proctor, VT.
Nestled in the quiet town of Proctor, VT, our home is located in a well established, local neighborhood where you'll find it easy to relax with the whole family. Our home makes a perfect basecamp whether you are visiting to hike, bike, fish, hunt, swim, boat, ski, snowboard, or take in the beautiful fall colors while touring the VT countryside, our home's central location will be the perfect place to come home to after your days adventures!
LocationFamilyAccess
5.0 out of 5 average rating, 27 reviews
One Room School House. No Cleaning Fees!
Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace. Off-street parking. High speed internet and 65 inch Roku TV with surround sound. Three season screened porch. Also, we have recently introduced a NO CLEANING FEE policy as our way of saying "Thank You" for respecting our property and guidelines.
FamilyValueAccess
5.0 out of 5 average rating, 163 reviews
Baby Queens Barbie-core Studio Apt (dog friendly)
Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.
FamilyValuePets
4.86 out of 5 average rating, 293 reviewsPopular amenities for Proctor holiday rentals
Other great holiday rentals in Proctor

Your Cozy Basecamp for Adventure
FamilyValueCleanliness
4.96 out of 5 average rating, 73 reviews
Alynn's Hideaway
LocationFamilySleep quality
5.0 out of 5 average rating, 32 reviews
Luxury, downtown apt w/ balcony close to skiing
FamilyLocationLaundry
4.93 out of 5 average rating, 75 reviews
Summer Lodge Near Killington w/ Pool Table
ValueFamilyView
4.91 out of 5 average rating, 78 reviews
4 bedroom home w/mountain views & outdoor pool
FamilyValueSkiing
4.79 out of 5 average rating, 47 reviews
Pastoral Pittsford Home
FamilyLocationCleanliness
5.0 out of 5 average rating, 20 reviews
*Pet Friendly* The Madden Mountain Home
FamilyLocationQuiet
4.98 out of 5 average rating, 85 reviews
The FROG (Finished Rooms Over Garage) @ Bunny Hill
FamilyValueComfort
4.99 out of 5 average rating, 89 reviewsDestinations to explore
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- West Mountain Ski Resort
- Fort Ticonderoga
- Gore Mountain
- Middlebury College
- Hildene, The Lincoln Family Home
- Killington Resort
- Emerald Lake State Park
- Bromley Mountain Ski Resort
- Montshire Museum of Science
- Trout Lake
- Warren Falls
- Camp Plymouth State Park
- Shelburne Vineyard
- Quechee Gorge
- Jamaica State Park
- Six Flags Great Escape Lodge & Indoor Water park





