A winding road surrounded by autumn foliage.

Rutland Vacation Rentals

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Check prices for these dates

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

Our top choices for Rutland vacation 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.
$209 nightly
The price is $236
Sep 23 - Sep 24
Total with taxes and fees
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A bedroom with a bed, curtains, a radiator, and a view of the outside.

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
$193 nightly
The price is $196
Sep 29 - Sep 30
Total with taxes and fees
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.
$424 nightly
The price is $480
Sep 27 - Sep 28
Total with taxes and fees
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
$300 nightly
The price is $336
Sep 25 - Sep 26
Total with taxes and fees
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
$658 nightly
The price is $737
Sep 23 - Sep 24
Total with taxes and fees
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.
$1,113 nightly
The price is $1,224
Oct 9 - Oct 10
Total with taxes and fees
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.
$1,258 nightly
The price is $1,396
Oct 9 - Oct 10
Total with taxes and fees
Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.
A bedroom with a bed, two bedside tables, and a nightstand.

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.
$389 nightly
The price is $395
Sep 29 - Sep 30
Total with taxes and fees
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.
$241 nightly
The price is $272
Sep 23 - Sep 24
Total with taxes and fees
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.
$324 nightly
The price is $366
Sep 23 - Sep 24
Total with taxes and fees
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.
$417 nightly
The price is $460
Sep 23 - Sep 24
Total with taxes and fees
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.
$315 nightly
The price is $356
Sep 23 - Sep 24
Total with taxes and fees
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.
$523 nightly
The price is $591
Sep 23 - Sep 24
Total with taxes and fees
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.
$430 nightly
The price is $486
Sep 27 - Sep 28
Total with taxes and fees
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.
$317 nightly
The price is $358
Sep 23 - Sep 24
Total with taxes and fees
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, (22 reviews)
"Cannon was cozy, clean, and as described. "
United States
Addams S.
$428 nightly
The price is $484
Sep 23 - Sep 24
Total with taxes and fees
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.
$648 nightly
The price is $733
Sep 23 - Sep 24
Total with taxes and fees
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.
$347 nightly
The price is $392
Sep 23 - Sep 24
Total with taxes and fees
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.
$284 nightly
The price is $321
Sep 24 - Sep 25
Total with taxes and fees
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.
$557 nightly
The price is $609
Sep 23 - Sep 24
Total with taxes and fees
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

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"This is a beautiful clean well accommodated property on the edge of a magnificent pond. Ive nothing but positive memories and will definitely return."
E William 1-night trip
Posted 12 hours ago
Mountain Meadows Lodge

Find out more about Rutland

Everything you need to know about Rutland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rutland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rutland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Rutland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $233 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Rutland rentals

At Expedia, we put the best Rutland vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Rutland?

Yes, there are vacation rentals in Rutland near Vermont State Fairgrounds, or you can choose a more remote option if you're looking for extra privacy while you relax. 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 vacation.

What are some of the best vacation rentals in Rutland?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental outside of Rutland is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Rutland?

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

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 vacation rentals like in Rutland?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Rutland. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family trips or small group gatherings.