A winding road surrounded by autumn foliage.

Rutland Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Rutland holiday rentals

1 bedroom, desk, free WiFi, bed sheets

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 HK$777
HK$1,537 total
includes taxes & fees
29 Sept - 30 Sept
Cozy Rutland Retreat
Private kitchen

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 HK$727
HK$1,850 total
includes taxes & fees
29 Sept - 30 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Coffee/tea maker, fridge, microwave, oven

3. Centrally located apartment for the skier & outdoor enthusiast

Centrally located apartment for the skier & outdoor enthusiast
Rutland
The price is HK$1,030
HK$2,636 total
includes taxes & fees
23 Sept - 24 Sept
Centrally located apartment for the skier & outdoor enthusiast
Dining

4. 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 HK$1,538
HK$3,936 total
includes taxes & fees
11 Oct - 12 Oct
large ski ranch hot tub close to killington pets ok
Microwave, oven, stovetop, dishwasher

5. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is HK$3,060
HK$5,869 total
includes taxes & fees
29 Sept - 30 Sept
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
TV, fireplace, music library, video library

6. Cortina Mountain Chalet - Outdoor Hot Tub - Close to Pico and Killington Mountains

Cortina Mountain Chalet - Outdoor Hot Tub - Close to Pico and Killington Mountains
Mendon
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was great and well taken care of. The location was superb!"
United States
Juan P.
The price is HK$3,452
HK$10,015 total
includes taxes & fees
9 Oct - 10 Oct
Cortina Mountain Chalet - Outdoor Hot Tub - Close to Pico and Killington Mountains
4 bedrooms, iron/ironing board, free WiFi, bed sheets

7. 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 HK$1,702
HK$3,318 total
includes taxes & fees
29 Sept - 30 Sept
4BR Home | Walk Downtown Rutland + Trails
Dining

8. Killington resort: Walk to Mountain, Bike, Pool

Killington resort: Walk to Mountain, Bike, Pool
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent location. Clean and easy."
United States
Todd I.
The price is HK$875
HK$2,744 total
includes taxes & fees
21 Sept - 22 Sept
Killington resort: Walk to Mountain, Bike, Pool
Exterior

9. Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Killington
8.0 out of 10, Very good, (1 review)
The price is HK$558
HK$1,961 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
TV, fireplace, DVD player, books

10. Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is HK$733
HK$2,979 total
includes taxes & fees
21 Sept - 22 Sept
Resort condo with mountain views, full kitchen, and free WiFi
Property grounds

11. Beautiful 1-bedroom cabin with AC in wonderful Wells

Beautiful 1-bedroom cabin with AC in wonderful Wells
Wells
10.0 out of 10, Exceptional, (1 review)
"We last minute booked this place just for a place to sleep that night. What we found was much more beauty. A place you could just sit outside watching the mountains and sky. The owners are as sweet as can be! We definitely want to come back soon for a quiet beautiful view!"
United States
Melissa
The price is HK$883
HK$1,164 total
includes taxes & fees
21 Sept - 22 Sept
Beautiful 1-bedroom cabin with AC in wonderful Wells
Coffee/tea maker, fridge, microwave, oven

12. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Killington
9.6 out of 10, Exceptional, (71 reviews)
"Cozy space close to the mountain. Host was very responsive and check in and check out was easy. "
United States
Spencer P.
The price is HK$851
HK$2,807 total
includes taxes & fees
23 Sept - 24 Sept
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Aerial view

13. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"I enjoy the location "
United States
troy
The price is HK$612
HK$1,826 total
includes taxes & fees
21 Sept - 22 Sept
Mountain Green
1 bedroom, desk, iron/ironing board, travel cot

14. Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (17 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
United States
Joseph S.
The price is HK$988
HK$2,136 total
includes taxes & fees
21 Sept - 22 Sept
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Golf

15. BearNecessities- Pool, Hot Tub, Gym

BearNecessities- Pool, Hot Tub, Gym
Killington
10.0 out of 10, Exceptional, (3 reviews)
"The unit was right across from Killington with many great amenities. The place was very cozy and perfect for a quick stay before a day of skiing."
United States
Matthew S.
The price is HK$946
HK$2,594 total
includes taxes & fees
21 Sept - 22 Sept
BearNecessities- Pool, Hot Tub, Gym
Exterior

16. Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Killington
8.0 out of 10, Very good, (6 reviews)
"I don’t think I’ve ever had such wonderful service checking in and caring for our needs. Amazing response time and outstanding stay. Thank you."
United States
Margaret L.
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Terrace/patio

17. CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Killington
9.8 out of 10, Exceptional, (26 reviews)
"Great trip!"
United States
casey d.
CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Interior

18. 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 HK$988
HK$2,136 total
includes taxes & fees
24 Sept - 25 Sept
CozyDen - AC, Bike to Mountain, Porch!
TV, stereo

19. 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 HK$2,757
HK$5,243 total
includes taxes & fees
26 Sept - 27 Sept
Killington Retreat | Deck-Fire Pit-Mountain Views!
Indoor pool, a heated pool

20. Modern Mountain Condo with Spa

Modern Mountain Condo with Spa
The Woods
9.4 out of 10, Exceptional, (12 reviews)
"The property met our expectations. Great property for parties less than 6 people."
United States
Michael H.
Modern Mountain Condo with Spa
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
"I thought the cabins were very unique and very nicely done. Everything was clean when we arrived. It was a little confusing about the check-in, but someone came to our aid. We enjoyed our stay. One thing that was wrong. Was we came home at night after dinner out and we were planning to take a shower and the water was trickling and cold. It was like there was no water on the property. It was already late so we did not contact anyone and the next morning, the water was working. This is a problem that needs to be looked at."
annemarie 3-night trip
Posted 3 hours ago
Emrose Luxury Cabins

Find out more about Rutland

Search for holiday rentals in Rutland on Expedia! You can easily find your home rentals, villas, holiday apartments in Rutland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Rutland!

Frequently asked questions

Can I find a holiday rental in Rutland?

Yes, there are holiday rentals in Rutland close to Vermont State Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Rutland speak highly of the ski slopes and array of shops. Make sure to also enjoy the majestic mountain landscape and top-notch restaurants during your holiday.

What are some of the best holiday rentals that Rutland has to offer?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of Rutland is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Rutland?

Choose from 54 Expedia holiday rentals in Rutland for a memorable holiday.

What can I see and do in Rutland?

Cultural attractions include Paramount Theater and Chaffee Art Center, whereas Pine Hill Park and Green Mountain National Forest are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Vermont State Fairgrounds and Killington Resort.

What are holiday rentals like in Rutland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Rutland. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.