Holiday Rentals in Rutland

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Holiday Rentals in Rutland

Stunning Wedding & Retreat Venue (19 bedrooms)

10.0 out of 10, Exceptional, (2)
"Our corporate group had an incredibly fun stay at Red Clover for a recent ski retreat. The property is impeccably maintained, staff are all very friendly and hospitable, and were communicative before and during our stay. The Red Clover team welcomed our group with open arms (and fresh baked cookies to boot!). It was the perfect setup for our group of ~25, and we appreciated the variety of sleeping rooms, and the number of rooms available. We also loved the dining area and the fact that it could...
Stunning Wedding & Retreat Venue (19 bedrooms)

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (63)
"Everything was great! Very clean & cozy. Perfect spot for a ski trip!"
The price is €270
includes taxes & fees
4 Feb - 5 Feb
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (181)
"We all had a wonderful time, enjoying this cozy, homey cabin, and the fantastic view over Perch Pond. We were comfortable inside, and took many walks outside... beautiful!"
The price is €176
includes taxes & fees
29 Jan - 30 Jan
Ultimate relaxing vacation

Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

10.0 out of 10, Exceptional, (163)
"This Vermont home is the perfect getaway in the winter. Deb and Ang have beautiful land for all of your cold weather needs. Their home is equipped with a REAL fireplace. Book here and you will not regret it!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (42)
"My fiancé and I stayed here over Christmas break for 4 nights. Snowboarded on Killington for 3 of those days. We were in close proximity to not only the mountain, but the shops to get our boards waxed and restaurants/bars. Those restaurants/bars were essential as this rental unit only has a microwave and mini fridge (as advertised). But for a place to just kick back and relax, clean up, and sleep. It was in a prime location. The spa services were available to us and while we didn't get to use...
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Beautiful Myrtle Beach Condo with Amenities Galore

8.8 out of 10, Excellent, (162)
"This was a really nice spacious property. It was very clean and in a nice location. "
Beautiful Myrtle Beach Condo with Amenities Galore

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (90)
"Our stay was nice and cozy! The condo held our family nicely and it had everything we needed— we especially loved the coffee bar. It was an easy drive into town and very picturesque. "
Beautifully renovated with fireplace and coffee bar

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (35)
"Convenient to Okemo. Has everything you need for a ski week or weekend! "
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside

10.0 out of 10, Exceptional, (163)
"Great condo. Ski in/out was nice. Living room was comfortable with a nice fireplace and tv. Beds and bedrooms were clean and comfortable. Kitchen clean and well equipped. Hot tubs and pool at the clubhouse were busy, but that was no surprise on a holiday weekend."
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (200)
"My family and I just returned from our New Years stay at “Cozy Cottage”. The home is beautifully appointed and equipped with everything you could possibly need. Waking up every morning in the sun room overlooking the lake was an absolute dream especially on a snowy day. The location is fantastic, as it’s a stones throw to Okemo, and about a 7 min drive to the town of Ludlow where you will find a grocery store, quaint shops, and dining. We definitely plan to return!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (19)
"Great Location! Very short drive to Skyeship Gondola. Property was well equipped for all our needs."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (165)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.6 out of 10, Excellent, (26)
"We were a bit disappointed with this property. The pictures are a bit misleading as it felt dark and stuffy, which we didn’t expect. There was a strong cigarette odor that was hard to adjust to and the room kept dropping down to very cold temperatures (50s) even after we adjusted the thermostat. This was stressful since we have a 15 month old and were worried about her being too cold all night. The deck was completely blocked by a mound of treacherous ice from water dripping off the roof, which...
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.2 out of 10, Wonderful, (15)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (20)
"The place is everything it describes, however I missed the part where the bathrooms are in a separate building and they are shared. Thankfully for us there was nobody else staying there. Everything was very clean. Other than that I was satisfied. "
The price is €183
includes taxes & fees
27 Jan - 28 Jan
Treehouse at Wise Pines- SoBo

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

7.6 out of 10, Good, (50)
"This cozy cabin was perfect for a ski weekend with friends. We really enjoyed gathering by the stone fireplace after a couple long days out on the slopes."
The price is €531
includes taxes & fees
4 Feb - 5 Feb
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Amazing Mountain Condo - Right across the street to Killington Resort

9.8 out of 10, Exceptional, (168)
"It was cozy, clean, and in the greatest location. "
Amazing Mountain Condo - Right across the street to Killington Resort

Comfortable mountain gem with pool, mountain views, & indoor parking space

8.4 out of 10, Very good, (26)
"This is a perfect property very close to the Snowden lodge. Easy access and perfect size. Great amenities. Will definately stay here again."
The price is €315
includes taxes & fees
26 Jan - 27 Jan
Comfortable mountain gem with pool, mountain views, & indoor parking space

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (198)
"We had a great stay. Cabin was cozy and warm while it was cold and blustery outside. Hot tub was a welcome perk. Bed was comfy. Regulating the heat upstairs took a littlelittleexperimentation.but we gor it. Stairs are steep! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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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Other types of properties in Rutland you may be interested in

Comfort Inn Rutland - Killington

2.5 star property
8.0 out of 10, Very good, (1009)
"nice"
The price is €132
includes taxes & fees
26 Jan - 27 Jan
Comfort Inn Rutland - Killington

Days Inn by Wyndham Rutland/Killington Area

2.5 star property
6.4 out of 10, (1003)
"We had two pets that were with us and one was a service animals which the accommodation was well met, "
The price is €134
includes taxes & fees
30 Jan - 31 Jan
Days Inn by Wyndham Rutland/Killington Area

Best Western Inn & Suites Rutland-Killington

2.5 star property
8.8 out of 10, Excellent, (1000)
"Comfortable, quiet, friendly staff, a lot of options for breakfast."
The price is €189
includes taxes & fees
4 Feb - 5 Feb
Best Western Inn & Suites Rutland-Killington
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.

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?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: This holiday home rental outside of Rutland is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Rutland?

Choose from 42 Expedia holiday rentals in Rutland for a memorable holiday.

What can I see and do in Rutland?

Family-friendly attractions include Green Mountain Rock Climbing Center and Hathaway Farm, whereas Green Mountain National Forest and Pine Hill Park are a couple of great spots to enjoy the outdoors. Other places in town to visit include Paramount Theater and Vermont State Fairgrounds.

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.