A winding road surrounded by autumn foliage.

Holiday Homes in Rutland

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Rutland holiday homes

A bedroom with a bed, curtains, a radiator, and a view of the outside.

1. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is AU$269
includes taxes & fees
29 Sept - 30 Sept
Cozy Rutland Retreat
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

2. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is AU$333
includes taxes & fees
16 Sept - 17 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

3. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.0 out of 10, Wonderful, (8 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AU$687
includes taxes & fees
27 Sept - 28 Sept
large ski ranch hot tub close to killington pets ok
A modern kitchen with white cabinets, stainless steel appliances, a window with a view, and a 'GATHER' sign above the window.

4. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is AU$1,027
includes taxes & fees
16 Sept - 17 Sept
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
A bedroom with a bed, two bedside tables, and a nightstand.

5. 4BR Home | Walk Downtown Rutland + Trails

4BR Home | Walk Downtown Rutland + Trails
Rutland
10.0 out of 10, Exceptional, (7 reviews)
"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "
United States
Dominic C.
The price is AU$586
includes taxes & fees
16 Sept - 17 Sept
4BR Home | Walk Downtown Rutland + Trails
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

6. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
The price is AU$579
includes taxes & fees
20 Sept - 21 Sept
Killington Retreat | Deck-Fire Pit-Mountain Views!
A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

7. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is AU$411
includes taxes & fees
29 Sept - 30 Sept
Luxury Condo Tucked in the Heart of Killington
A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

8. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AU$379
includes taxes & fees
15 Sept - 16 Sept
CozyDen - AC, Bike to Mountain, Porch!
A modern living room with a dark gray sectional sofa, a white armchair, a wooden coffee table, and a spiral staircase.

9. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is AU$1,360
includes taxes & fees
13 Sept - 14 Sept
Slopeside Estate Guesthouse: Hot tub, AC, Grill
A red building with a gabled roof, surrounded by a well-maintained grassy field and dense trees.

10. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is AU$800
includes taxes & fees
16 Sept - 17 Sept
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A cozy living room with a fireplace, a television, and a view of a snowy deck.

11. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Killington
9.8 out of 10, Exceptional, (59 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is AU$1,032
includes taxes & fees
16 Sept - 17 Sept
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

12. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is AU$673
includes taxes & fees
13 Sept - 14 Sept
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A cabin with a wooden deck, surrounded by lush greenery and a garden with purple flowers.

13. Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
Killington
10.0 out of 10, Exceptional, (1 review)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
United States
Catherine S.
The price is AU$895
includes taxes & fees
14 Sept - 15 Sept
Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

14. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
The price is AU$1,001
includes taxes & fees
14 Sept - 15 Sept
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
A wooden interior with a bench and shelves, a door with a handle, and a tiled floor.

15. The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals

The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"Great amenitiesCleanNewAnd easy access to Starship Gondola at KillingtonWent with my two sons - we had a great time"
United States
Gifford F.
The price is AU$686
includes taxes & fees
16 Sept - 17 Sept
The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
A bedroom with a wooden bed, a nightstand, a lamp, a window with blinds, and a wall-mounted light fixture.

16. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
Killington
The price is AU$661
includes taxes & fees
15 Sept - 16 Sept
Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
A cozy living room with a brick fireplace, a sofa, a coffee table, and a television mounted on a wooden cabinet.

17. The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Killington
10.0 out of 10, Exceptional, (21 reviews)
"Great location and excellent hosts "
United States
Peter G.
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
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.

18. 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 AU$820
includes taxes & fees
13 Sept - 14 Sept
Ski Home/Arcade Mountain Views Near Killington/Woodstock

19. 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 AU$773
includes taxes & fees
13 Sept - 14 Sept
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

20. 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.
The price is AU$896
includes taxes & fees
14 Sept - 15 Sept
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
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 Rutland Hotel Reviews

Emrose Luxury Cabins

Emrose Luxury Cabins

10/10 Excellent
"Great place. Easy access. Highly recommended"
Ariel 2-night trip
Posted 6 hours ago
Emrose Luxury Cabins

Find out more about Rutland

Rutland Holiday Homes information

Number of reviews
173
Accommodation
884 Holiday Homes
Lowest Price
AU$269
Highest Price
AU$1,032