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

Holiday Homes in Randolph

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Randolph holiday homes

A rustic cabin surrounded by autumn foliage.

1. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.0 out of 10, Wonderful, (12 reviews)
"We had a great stay - Quiet, clean, cozy, and a great location, we'll definitely stay here again for future trips!"
United States
Sloan S.
Beautiful home located in the Mad River Valley
A wooden barn with a large open door, a small cart, and a grassy area in front.

2. Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Chelsea
10.0 out of 10, Exceptional, (56 reviews)
"Dave & Miken were fantastic hosts - excellent communications and so nice & welcoming. It was fun to milk the goats and hold the babies. Loved the dogs, ducks and chickens too,"
United States
Martha
The price is €258
includes taxes & fees
1 Oct - 2 Oct
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Winter Wonderland

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

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is €681
includes taxes & fees
12 Oct - 13 Oct
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A rustic cabin surrounded by autumn foliage.

4. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.8 out of 10, Exceptional, (27 reviews)
"We had a great time! "
United States
Allie T.
Beautiful home located in the Mad River Valley
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.

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

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is €515
includes taxes & fees
30 Sept - 1 Oct
Ski Home/Arcade Mountain Views Near Killington/Woodstock
A room with a large window overlooking a forest in autumn.

6. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.4 out of 10, Exceptional, (49 reviews)
"Nice location off of Route 100 there was a little road noise but the house is situated a bit back. The seating was super comfy and the kitchen was nicely stocked for cooking. It was awesome to be able to bring our pup! "
United States
Melissa P.
Beautiful home located in the Mad River Valley
A room with a large window overlooking a deck with two chairs and a table.

7. Luxurious Vermont home minutes from Sugarbush Resort

Luxurious Vermont home minutes from Sugarbush Resort
Warren
10.0 out of 10, Exceptional, (44 reviews)
"Perfect location for ski vacation. House was clean, close to resort. Quick drive to restaurants, looking forward to staying again! "
United States
Noah S.
Luxurious Vermont home minutes from Sugarbush Resort
A modern kitchen with wooden cabinets, stainless steel appliances, and large windows offering a view of the outdoors.

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

Chalet Valhalla with Hot Tub right next to Sugarbush Resort
Fayston
10.0 out of 10, Exceptional, (10 reviews)
"The hot tub was very nice and the stay was LOVELY. "
United States
Nicole B.
The price is €609
includes taxes & fees
4 Oct - 5 Oct
Chalet Valhalla with Hot Tub right next to Sugarbush Resort
A covered porch with a view of a white house and a green lawn.

9. 150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!

150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Bethel
10.0 out of 10, Exceptional, (3 reviews)
"Lovely home with a beautiful property and accurate listing."
United States
Anonymous traveller
The price is €1,206
includes taxes & fees
30 Sept - 1 Oct
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
A two-story house with a covered porch, outdoor seating, and a lawn.

10. Classic Vermont Farmhouse near Sugarbush Resort

Classic Vermont Farmhouse near Sugarbush Resort
Warren
9.6 out of 10, Exceptional, (57 reviews)
"Great location for skiing at Sugarbush. Nice big living room for the whole group to gather. "
United States
Peggy V.
Classic Vermont Farmhouse near Sugarbush Resort
A cozy living room with a stone fireplace, wooden walls, a leather sofa, and a dining area.

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

Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
Hancock
10.0 out of 10, Exceptional, (1 review)
"The maple castle was awesome! Definitely the most unique house I have ever stayed in. You can sit in the hot tub and watch the river or you can walk down a tiny hill to tie up a tube and float in it. The owners were extremely helpful and responsive. Would definitely recommend. "
United States
Katie H.
The price is €840
includes taxes & fees
2 Oct - 3 Oct
Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

12. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is €260
includes taxes & fees
30 Sept - 1 Oct
Luxury Condo Tucked in the Heart of Killington
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

13. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
A log cabin interior with a stone fireplace, a sofa set, a round table, and a large window offering a view of the outdoors.

14. Ridge House - Modern Log Home Nestled on top of a Private Mountain

Ridge House - Modern Log Home Nestled on top of a Private Mountain
Waitsfield
10.0 out of 10, Exceptional, (17 reviews)
"A gorgeous house, well designed, incredibly comfortable & perfectly appointed. Responsive staff at the mgmt company too. We will be back!"
United States
lauren m.
Ridge House - Modern Log Home Nestled on top of a Private Mountain
A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

15. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
10.0 out of 10, Exceptional, (1 review)
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A dining area with a wooden table, four chairs, a coffee maker, and a trash can.

16. Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
Chittenden
9.4 out of 10, Exceptional, (6 reviews)
"Loved this stay - the farmhouse is authentic and oozes charm! Everything about this stay was easy - 20min drive to the slopes, 15 min to downtown Rutland, and an extremely well-equipped house to easily accommodate the six of us. Superb communication from the host both prior to and during our stay (promptly answered several questions for us). If you want a vintage farmhouse feel as opposed to a modern condo-style stay, this is the place for you!"
United States
Carl P.
The price is €469
includes taxes & fees
30 Sept - 1 Oct
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
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

Large multi-family ski home located on the slopes of Sugarbush Resort
Warren
10.0 out of 10, Exceptional, (31 reviews)
"The skiing was fantastic. Thanks for a great stay."
United States
James K.
Large multi-family ski home located on the slopes of Sugarbush Resort
A spacious living room with a fireplace, a television, and a large window.

18. 4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
North Sherburne
10.0 out of 10, Exceptional, (23 reviews)
"Our group had a wonderful ski weekend at the house! It was well stocked with everything we needed and the fireplace was perfect to relax near after a day on the slopes. "
United States
Christina V.
4BR Killington Home Perfect for Families, Pet-Friendly
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

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

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
6.8 out of 10, (3 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is €676
includes taxes & fees
13 Oct - 14 Oct
The Tower House | Hot Tub | Firepit | Dog-Friendly
A spacious living area with a fireplace, a television, and a dining area with natural light.

20. Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Killington
7.0 out of 10, Good, (6 reviews)
"Excellent brief stay."
United States
Ron L.
The price is €566
includes taxes & fees
30 Sept - 1 Oct
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Randolph Hotel Reviews

Brandon Inn

Brandon Inn

8/10 Good
"The staff were incredibly kind and welcoming throughout my stay. While the inn is a beautiful historic home filled with marble floors and intricate architectural details, I was pleasantly surprised that my room also had some of the best air conditioning I've ever slept with.The staff are exceptionally kind, the historic property is full of beautiful details, and the marble floors add to its charm.The inn itself is a beautiful historic property with marble floors and gorgeous details throughout."
SAU MUI 1-night trip
Posted 4 hours ago
Brandon Inn

Find out more about Randolph

Randolph Holiday Homes information

Number of reviews
343
Accommodation
635 Holiday Homes
Lowest Price
€258
Highest Price
€1,206