Holiday rentals with breakfast in Rutland County

Mountaintop Getaway

Take it easy at this unique and tranquil getaway. Located in the beautiful village of Wells, VT. 8 miles from Lake St. Catherine where boats are available for a day of fishing or just riding around. Whaleback Vineyard for wine tasting is 16 miles. Miniature Golf course is 13 miles. Bromley Mountain (~25-30 mins), Magic Mountain (~30-35 mins), or Stratton Mountain (~40-45 mins). These options offer varied terrain for all skill levels and are within easy driving distance Free Cont. Breakfast

Clear River Inn - 2 Bedroom Suite

Live the "Suite Life" at the Clear River Inn in this spacious 2BR, 1-bath suite. Featuring 4 beds between 2 large bedrooms separated by an open kitchen, dining, and living area - this suite perfect for keeping the crew together, or if you just want bragging rights for booking THE spot. Centrally located on scenic Route 100, minutes from skiing, snowmobiling, hiking & more. Enjoy the daily Breakfast Nook & unwind at the Clear River Tavern Weds–Sun, just steps away. Free disc golf course onsite!

2026/2027 skiseason 3/4BdrmAvailable for halfshare

Please disregard displayed pricing and inquire for details / pricing options. Located around the corner from the main base & on shuttle route. Fully renovated, townhome located in the quiet community. This 4 bdrm, 2.5 bath home offers a gracious floor plan. Main level offers open concept living with a wood burning fireplace. Upper level features private suite with bathroom. Lower level has 3 bdrm, full bath, and laundry. Expansive mudroom and wrap around deck w/ covered porch and hot tub.

Luxe Farmhouse Mins to Okemo - Hot Tub & Fire Pit!

- 9 min to Jackson Gore at Okemo; 25 min to Killington - 8 seat Jacuzzi hot tub - Solo Stove for Apres Ski S'mores - Gear Dryer in the mudroom to air out all your ski gear - Grill on the deck for a night cooking in - Coffee/cocktail station w/ Keurig coffee maker - Arcade machine with over 3,500 games - Sonos speakers by the hot tub and in the kitchen/living room area - Towel warmer by the hot tub - Great sledding hill in the side yard - Wrap around porch with sunset views - Two car garage

The Chalet at The Snowed Inn

Keep it simple at this peaceful and centrally-located place. The Chalet is a separate unit located at The Snowed Inn, a 5-star Inn in Vermont, offering 2 floors - top floor is large studio space with bed, couch, kitchen, jacuzzi tub, fireplace, balcony. Bottom floor offers pull out couch with large screen TV. The Inn offers complimentary breakfast, 24 hr coffee/tea & outdoor hot tub. Enjoy sitting at the bar and choose from our wine/beer list and pub menu. 1 mile from Killington Mt.

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.

Endless Brook Farm B&B w Sauna, Hot Tub, Breakfast

Our home is located in a quiet, beautiful valley, surrounded by 175 acres of gardens, fields, hills, trails, streams, ponds and woods. Our bedrooms are bright and airy, with private bathroom upstairs on your own floor. Breakfast is provided each day -- all natural foods, special diets accommodated. 3-5 mins from Slate Valley Trails and Lake St. Catherine/State Park. 5 mins to Wells center. 10 mins to Poultney. 30 mins to Manchester or Rutland, VT.

The Summit Cottage, Killington | 2BR/2BA Sleeps 6

The Summit Cottage is the perfect home base for a Vermont ski getaway. Nestled in the heart of Killington and just 3 miles from the slopes, it offers both convenience and comfort. After a full day on the mountain, where your group can relax, cook meals, and unwind together. Thoughtfully designed to sleep up to 6 guests, the cottage is ideal for couples, small families, or friends seeking a comfortable retreat just steps from the Summit Lodge.

Trestle Farm

Trestle Farm, formerly a 50-year old horse rescue ranch, which we are transforming into a floriculture farm. 12 acres of open meadows to enjoy. If you’re looking for a bit of old, rustic Vermont, Trestle Farm offers all you need for a peaceful getaway, and yet it is just minutes to Rutland. With over 30 years of estate caretaking experience we welcome you to Trestle Farm to share this special Vermont hideaway.

Deluxe Suite (Mountain Sports Inn)

This is a 2000 square ft home located right on the Killington Rd leading up to the mountain. This is a 3 bedroom(1 king, 1 queen & 2 twin), 2.5 bath, full kitchen & full living room. Hot Breakfast included Dec-Mid March. Continental Breakfast Included Memorial Weekend-Mid Oct & Mid Nov-Mid April (Message for specifics) Require 2 Night Minimum on most holiday weekends. Quiet Hours: 10pm

Vermont Country Suite

Located in Chittenden, VT, we are in the heart of the Green Mountains. We are just down the road from the Mountain Top Inn wedding venue and Cross Country Skiing Center. The apartment is an easy 15-20 minute drive to Pico and Killington ski areas. The suite is perfect for winter and summer adventuring or just a quiet get away in Vermont.

Lake Bomoseen 2 BR Cottage

Maple Cottage is a newly renovated 2-bedroom cottage. This unit features two 2nd floor king bedrooms, one bathroom, full kitchen, living room and front porch overlooking beautiful Lake Bomoseen. The Lake Bomoseen Lodge properties include access to hotel amenities and an on-site Taproom.