Holiday rentals with breakfast in Rutland County

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!

Family · Value · Access

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.

Family · Location · Getting around

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

Value · Location · Kitchen

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.

Family · Value · Cleanliness

MT Retreat / Killington, Woodstock, Rutland, Okemo

We also offer our beautiful grounds as a venue for tented events. Bewitching views. Quiet, private suite. C. bkfst. Winter garage! COVID: “VT Forward” guidelines followed. Consider a private cooking class from award-winning Chef Ted and enjoy the foods of your labor in a lovely natural setting. BYOB. See Odyssey Events VT & Airbnb Experiences for cooking options. FYI, Bedroom size: 9' x 14'. Adjoining bathroom: 8' x 9'. The ante-room/office: 8' x 12', which is also yours to use.

Location · Value · Wi-Fi

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.

Family · Value · Accuracy

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.

Location · Amenities · Sleep quality

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.

Family · Value · Hiking

Cozy private room - Killington

Charming comfortable bedroom in a private home set on a beautiful property, which is located only minutes from Killington, the northeast’s premier ski and golf resort. The residence is situated close to hiking trails, bicycling, fishing, kayaking, skiing, golfing, and Mendon Bikram Yoga. The Blue bedroom offers a queen size bed with a shared bathroom and steam room...

Value · Location · Pets

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.

Family · Value · Condition

Resort Property near Killington

Four Pines is a spacious, flowing house with numerous, comfortable living spaces – including an oversized kitchen, 3 living areas and an expansive deck. Located at Mountain Top Resort we have access to several of the Resorts amenities and a short drive to Killington or Pico Mountains.

Location · Hospitality · Access

6 Bedroom Lakeside Cottage

The Pine Cottage is a 6 bedroom house with full kitchen, living room and dining room. One bedroom has a king bed and the other bedrooms each have one queen. There are 6.5 bathrooms. Located at Lake Bomoseen Lodge, guests have access to the hotel amenities and on site Taproom.

Family · Value · Pool