Vacation rentals in Rutland

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.

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.

Killington/Okemo, 7p Hot tub, Mtn.views, Spacious!

Mid week deals! Killington Mnt-20min drive, Lake Bomoseen-20min, Pico Mnt-15min Okemo-30min, Downtown Rutland-5min (bars/dining/shopping) Mnt Top Inn-18min, Hiking-10 min. , Neighborhood pool with tennis courts, basketball courts, playground. Beautiful mnt views, peaceful brook on 1+ acre. Spacious home with hot tub, AC, firepit, fooseball table, grill, deck, patio, screenroom, 2 kitchens, 2 living rooms, washer/drier, fully stocked kitchens. Very fast wifi/netflix/youtubeTV/nintendo switch.

Luxury, downtown apt w/ balcony close to skiing

A luxurious apartment in the center of it all. Enjoy all Historic Downtown Rutland has to offer with some of the best restaurants, pubs, and lounges in the state just steps away. Snuggle up on the couch in front of the fireplace, or enjoy a local craft beverage on the balcony overlooking Center Street. This newly renovated apartment is the perfect base camp to quickly access the region's most sought after attractions. 17 minutes to Pico Mountain Ski Resort, 20 minutes to Killington Ski Area.

Nice, Large Modern Apartment

Super clean, downstairs apartment with large spacious rooms. Great place with lots of room for fun! Perfect for the whole family, or just one person looking for space. 2 Bedroom, Living, Dining, fully stocked kitchen, large yard. Right in the heart of Rutland. Walking distance to Downtown Rutland and The Paramount Theatre. Quiet location. Keyless entry, air conditioning and fast WI FI. 15 min. to Killington. 30 min. to Okemo. Lots of hiking and biking trails and great golf courses nearby!

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

Kingsley Homestead

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.

New Firepit, Great Location, Dog Friendly, Kitchen

Welcome to @MendonMtGetaway - my warm & cozy VT retreat! With 3 bedrooms, comfy living room, full kitchen, washer/dryer, AND office space - I hope you'll feel at home right away. You are in a wonderful location here. Turn left & you are just minutes down the road from ski heaven - Killington and Pico Mountains! Turn right, and you're just minutes from cute & historic Rutland. Either way you’ll find tons of great outdoor activities & hiking, and lots of local shops and restaurants.

Relaxing Retro Rutland Retreat

Keep it simple at this peaceful yet centrally-located one floor home. 15 minutes to the Killington ski area, in a quiet, tree-filled neighborhood where deer are often spotted in the yard! This home is recently renovated and decorated with a mid-century modern vibe. Two bedrooms, one with a king-sized bed and the other with twin beds. Den includes a desk and Wi-fi for ease of working remotely. Comfy living room features a large couch as well as an electric fireplace.

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.

Red Rooster: Cozy ADV hub on a urban micro-farm.

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.

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.