A winding road surrounded by autumn foliage.

Rutland Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Rutland holiday rentals

A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

1. 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$337
includes taxes & fees
27 Sept - 28 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A dining table set with plates, glasses, and a vase with a plant.

2. 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$275
includes taxes & fees
26 Oct - 27 Oct
Cozy Rutland Retreat
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$633
includes taxes & fees
27 Sept - 28 Sept
large ski ranch hot tub close to killington pets ok
A modern kitchen with stainless steel appliances, wooden flooring, and white cabinetry.

4. Centrally located apartment for the skier & outdoor enthusiast

Centrally located apartment for the skier & outdoor enthusiast
Rutland
The price is AU$461
includes taxes & fees
27 Oct - 28 Oct
Centrally located apartment for the skier & outdoor enthusiast
A modern kitchen with white cabinets, stainless steel appliances, a window with a view, and a 'GATHER' sign above the window.

5. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is AU$1,007
includes taxes & fees
26 Oct - 27 Oct
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
A spacious living room with a high ceiling, a fireplace, and a dining area with a chandelier.

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 AU$1,779
includes taxes & fees
9 Oct - 10 Oct
Cortina Mountain Chalet - Outdoor Hot Tub - Close to Pico and Killington Mountains
A rustic cabin with a stone fire pit, wooden deck, and a chimney.

7. Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.

Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.
Mendon
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful mountain home in a peaceful setting. Very thoughtfully designed and well maintained with everything you need to have a quiet getaway."
United States
Heidi S.
The price is AU$1,976
includes taxes & fees
9 Oct - 10 Oct
Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.
A modern kitchen with stainless steel appliances, a dining table, and a wooden floor.

8. 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$555
includes taxes & fees
29 Sept - 30 Sept
4BR Home | Walk Downtown Rutland + Trails
A bedroom with a large bed, a TV mounted on the wall, and a sliding door leading to a bathroom.

9. 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 AU$388
includes taxes & fees
28 Sept - 29 Sept
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

10. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
The price is AU$558
includes taxes & fees
28 Sept - 29 Sept
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A snow-covered outdoor area with a large arch structure, rocks, and a building in the background.

11. CubsCorner - Pool, Sauna, Gym, Close to Mountain!

CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Great location with access to both Pico and Killington Mountains!"
United States
Olaf G.
The price is AU$642
includes taxes & fees
28 Sept - 29 Sept
CubsCorner - Pool, Sauna, Gym, Close to Mountain!
A spacious restaurant with high ceilings, exposed ductwork, and a mix of wooden and metal furniture.

12. 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 AU$576
includes taxes & fees
1 Oct - 2 Oct
Killington resort: Walk to Mountain, Bike, Pool
A wooden cabin with multiple balconies and a stone chimney.

13. Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (58 reviews)
"Great stay. We really loved the ski in ski out feature. Host was responsive with any issues"
United States
Andrea W.
The price is AU$932
includes taxes & fees
28 Sept - 29 Sept
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
A living room with a sofa, coffee table, and fireplace. There is a large window and a balcony with outdoor furniture.

14. FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
The Woods
9.8 out of 10, Exceptional, (25 reviews)
"Loved the pool, sauna, and steam room. Really nice place, everything we needed. "
United States
Lisa N.
The price is AU$664
includes taxes & fees
27 Sept - 28 Sept
FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

15. 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 AU$541
includes taxes & fees
27 Oct - 28 Oct
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
A rustic interior with a stone fireplace, wooden beams, leather furniture, and a balcony with a view.

16. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Killington
10.0 out of 10, Exceptional, (23 reviews)
"Cannon was cozy, clean, and as described. "
United States
Addams S.
The price is AU$899
includes taxes & fees
28 Sept - 29 Sept
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
A cozy living room with a fireplace, a television, and a view of a snowy deck.

17. 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$1,481
includes taxes & fees
29 Sept - 30 Sept
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A cozy living room with a brick fireplace, two sofas, a coffee table, and a TV mounted on the wall.

18. Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great location!!"
United States
Nicholas C.
The price is AU$548
includes taxes & fees
28 Sept - 29 Sept
Killington condo 5 min to killington resort
A modern loft bedroom with a sloped ceiling, a fireplace, a large TV, and a balcony with a scenic view.

19. Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.

Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
Killington
10.0 out of 10, Exceptional, (14 reviews)
"A wonderful up to date property a short walk to the lifts! Would definitely stay here again."
United States
Mike B.
The price is AU$603
includes taxes & fees
28 Sept - 29 Sept
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
An indoor swimming pool with tiled flooring, a seating area with chairs, and large windows allowing natural light.

20. RabbitHole | AC, Pool, Hot Tub, Near Resort

RabbitHole | AC, Pool, Hot Tub, Near Resort
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Our hosts were super communicative. The check in process was smooth. The condo was clean and well appointed. Beds good. Our hosts even gave us some local coffee and maple syrup as a welcome gift (along with a few other things). Definitely recommend "
United States
Amy G.
The price is AU$868
includes taxes & fees
28 Sept - 29 Sept
RabbitHole | AC, Pool, Hot Tub, Near Resort
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
"This is a unique property. Very clean, great shampoos, comfortable beds. Bring your own food and snacks. The grounds are super clean and in a safe, private area. We had an issue with the arrival instructions not opening in email but a call to the property phone number got our issue resolved quickly. Everything was great."
Sherry 1-night trip
Posted 4 hours ago
Emrose Luxury Cabins

Find out more about Rutland

Everything you need to know about Rutland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rutland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rutland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Rutland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rutland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rutland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rutland holiday rentals we have selected for you start as low as AU$397 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Rutland rentals

At Expedia, we put the best Rutland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Rutland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rutland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rutland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 56 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.