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Rutland Vacation Rentals

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Our top choices for Rutland vacation rentals

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.6 out of 10, Exceptional, (5)
"Peaceful stay in the city! We were headed to the rodeo, so this was the perfect distance away! "
United States
Aislinn F.
The price is ¥14,677
¥32,877 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Cozy Rutland Retreat

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)
"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 ¥18,128
¥41,288 total
includes taxes & fees
Jan 7 - Jan 8, 2026
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
Rutland
9.2 out of 10, Wonderful, (5)
The price is ¥23,391
¥30,040 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Rutland
10.0 out of 10, Exceptional, (1)
The price is ¥29,753
¥67,205 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
2.0 star property
Mendon
9.8 out of 10, Exceptional, (11)
"Great place! Secluded but close to everything. We will definitely stay again."
United States
Patricia Y.
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
2.0 star property
Mendon
10.0 out of 10, Exceptional, (1)
"Amazing stay! Gorgeous house, clean, perfect location. The host was super responsive and made the check in check out process so easy.Highly reccomend and can’t wait to stay again next year. "
United States
Nicole H.
The price is ¥60,114
¥115,943 total
includes taxes & fees
Jan 11 - Jan 12, 2026
large ski ranch hot tub close to killington pets ok

Skiers! Fox Hollow 2BR/2BA Condo. Across from Pico, Minutes to Killington

Skiers! Fox Hollow 2BR/2BA Condo. Across from Pico, Minutes to Killington
Mendon
9.2 out of 10, Wonderful, (9)
"Easy in and out and a short ride to Killington"
United States
Paul K.
The price is ¥55,992
¥117,856 total
includes taxes & fees
Dec 28 - Dec 29
Skiers! Fox Hollow 2BR/2BA Condo. Across from Pico, Minutes to Killington

Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.

Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.
Rutland
9.2 out of 10, Wonderful, (5)
"Big and spacious. "
United States
Robert S.
Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.

Centrally located apartment for the skier & outdoor enthusiast

Centrally located apartment for the skier & outdoor enthusiast
2.0 star property
Rutland
4.0 out of 10, (1)
"The oven didn’t work and couldn’t get anyone to come turn a breaker back on! "
United States
Lynda M.
The price is ¥24,670
¥54,355 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Centrally located apartment for the skier & outdoor enthusiast

Skiers! Fox Hollow 2br/2ba Condo. Across From Pico, Minutes To Killington 2 Bedroom Condo

Skiers! Fox Hollow 2br/2ba Condo. Across From Pico, Minutes To Killington 2 Bedroom Condo
2.0 star property
Rutland
The price is ¥76,126
¥156,343 total
includes taxes & fees
Dec 28 - Dec 29
Skiers! Fox Hollow 2br/2ba Condo. Across From Pico, Minutes To Killington 2 Bedroom Condo

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is ¥18,425
¥52,350 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is ¥31,478
¥90,341 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.2 out of 10, Good, (44)
"Quick trip to and from Killington mt"
United States
Phillip F.
The price is ¥14,346
¥46,719 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Ben & Jerry’s Studio | 10 Min to Killington

Ben & Jerry’s Studio | 10 Min to Killington
Bridgewater
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is ¥17,019
¥35,687 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Ben & Jerry’s Studio | 10 Min to Killington

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
The price is ¥46,782
¥83,309 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is ¥29,473
¥54,991 total
includes taxes & fees
Jan 12 - Jan 13, 2026
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
Cavendish
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is ¥38,567
¥62,425 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Well-appointed studio right downtown - less than a mile to Okemo Mountain

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.6 out of 10, Excellent, (12)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
The price is ¥19,674
¥55,685 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.8 out of 10, Exceptional, (14)
"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "
United States
Ethan
The price is ¥23,391
¥29,164 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Treehouse at Wise Pines- NoBo

Cozy condo on ski shuttle route with free WiFi & full ktichen

Cozy condo on ski shuttle route with free WiFi & full ktichen
Killington
8.4 out of 10, Very Good, (38)
"Great place. Met our needs. "
United States
Sean K.
The price is ¥18,557
¥52,853 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Cozy condo on ski shuttle route with free WiFi & full ktichen
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

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 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?

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing: This vacation home rental outside of Rutland is located in the mountains and has an indoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a microwave, kitchenware, and a coffee maker. You can relax into your vacation with a garden and a hot tub.

How many vacation rentals are there in Rutland?

Choose from 49 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 popular places to visit in the area include Killington Resort and Okemo Mountain 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.