Randolph Vacation Homes

A porch with white railings and hanging flower baskets filled with pink flowers.

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Our top choices for Randolph holiday homes

A cozy living room with a sofa, armchair, and a bookshelf. There is a fireplace and a window providing natural light.

1. Authentic farmhouse for those who love cozy, quirky, historical imperfection

Randolph Center

Kathy K.

HK$5,133 total

includes taxes & fees

29 Oct - 30 Oct

A rustic cabin surrounded by autumn foliage.

2. Beautiful home located in the Mad River Valley

Warren

Allie T.

A room with a large window overlooking a forest in autumn.

3. Beautiful home located in the Mad River Valley

Warren

Melissa P.

4. Beautiful home located in the Mad River Valley

Warren

Sloan S.

A modern kitchen with wooden cabinets, a central island with stools, stainless steel appliances, and large windows offering a view of the outdoors.

5. Beautiful Country Home with Hot Tub & Pool Table

East Warren

Shenaugh K.

HK$7,400 total

includes taxes & fees

10 Nov - 11 Nov

A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

6. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge

Kevin M.

HK$4,820 total

includes taxes & fees

18 Oct - 19 Oct

7. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Stockbridge

Sophie L.

HK$4,779 total

includes taxes & fees

18 Oct - 19 Oct

A house with a stone staircase leading to a wooden deck, surrounded by lush greenery.

8. Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush

East Warren

Daniel B.

A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

9. Luxury Condo Tucked in the Heart of Killington

Killington

"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...

Melinda D.

HK$2,284 total

includes taxes & fees

9 Nov - 10 Nov

A two-story house with a covered porch, outdoor seating, and a lawn.

10. Classic Vermont Farmhouse near Sugarbush Resort

Warren

Peggy V.

A room with a large window overlooking a deck with two chairs and a table.

11. Luxurious Vermont home minutes from Sugarbush Resort

Warren

Noah S.

A cozy living room with a stone fireplace, wooden walls, a leather sofa, and a dining area.

12. Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace

Hancock

Katie H.

HK$8,826 total

includes taxes & fees

19 Oct - 20 Oct

A covered porch with a view of a white house and a green lawn.

13. 150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!

Bethel

Jamie R.

HK$10,723 total

includes taxes & fees

29 Oct - 30 Oct

A spacious living area with a fireplace, a curved staircase, and large windows offering views of the outdoors.

14. The Vines - 6000 sq. ft. Luxury Estate with Hot Tub & Mountain Views

East Warren

Brian S.

HK$10,831 total

includes taxes & fees

22 Oct - 23 Oct

A wooden deck with a hot tub and seating, overlooking a scenic landscape.

15. Sky Zen - Ridge Line Retreat

East Warren

Spyridon M.

HK$8,040 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with wooden cabinets, stainless steel appliances, and large windows offering a view of the outdoors.

16. Chalet Valhalla with Hot Tub right next to Sugarbush Resort

Fayston

Nicole B.

HK$5,737 total

includes taxes & fees

25 Oct - 26 Oct

A wooden cabin interior with a staircase leading to a balcony, large windows, and a view of a snowy forest.

17. Large multi-family ski home located on the slopes of Sugarbush Resort

Warren

James K.

A bedroom with a large bed, a sofa, a desk, and two windows.

18. The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

The Woods

HK$2,788 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor seating area with wicker chairs and a small table, surrounded by lush greenery and trees.

19. Entire Enchanting, Light-Filled 1830 Farmhouse

Waitsfield

Patti M.

HK$5,690 total

includes taxes & fees

29 Oct - 30 Oct

A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

20. The Tower House | Hot Tub | Firepit | Dog-Friendly

Killington

Patrick B.

HK$5,817 total

includes taxes & fees

21 Oct - 22 Oct

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Top Randolph Hotel Reviews

Mountain Meadows Lodge

10/10 Excellent

"Great views and quiet location. Comfortable communal areas, great walks around the surrounding forests and a wonderful spot to relax next to the lake. A short drive to Killington and all its attractions. Loved the cookies."

Secluded retreat in the trees

10/10 Excellent

"This is a gem! The carriage house is cozy, well appointed and had everything we needed and an incredible environment inside and out. From here we went to Montpelier, Warren and their 'almost world famous' general store, Lincoln Gap, Woodstock and Queechee. Each as a great day excursion with incredible leaf peeping on every road and mountain area. We went on fabulous hikes (short and long ones all over) every day all around our day excursions. The hosts are very friendly and kind and their two well behaved labs are an added bonus making it all feel like home. The kitchen, bathroom, bedroom and living area are all good sized, well stocked and comfortable. Attention to details make this a dream place set in a stunning rural setting."

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