Photo by Killington Resort

Holiday Rentals in Rutland

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Holiday Rentals in Rutland

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

2.5 star property
Rutland
The price is €168
includes taxes & fees
20 Nov - 21 Nov
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Mountain Green

2.0 star property
Killington
6.6 out of 10, (13)
"Great communication from Jeff."
United States
Dennis
The price is €240
includes taxes & fees
30 Nov - 1 Dec
Mountain Green

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
Killington
9.0 out of 10, Wonderful, (53)
"Clean and beautiful scenery "
United States
David
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ultimate relaxing vacation

Orwell
9.8 out of 10, Exceptional, (213)
"The cabin was wonderful and the view is to die for. Walking down to the dock and then taking it all in was a wonderful experience. "
United States
J
The price is €159
includes taxes & fees
24 Nov - 25 Nov
Ultimate relaxing vacation

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 €230
includes taxes & fees
2 Dec - 3 Dec
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow
8.0 out of 10, Very good, (41)
"Plenty of space and the two living rooms are great because the upstairs living room is very small."
United States
Brad H.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Killington Chalet - Great Space and Location!

The Woods
9.6 out of 10, Exceptional, (15)
"Our group of 10 friends had a wonderful stay at the Chalet. Great location to the mountain and local restaurants and entertainment. Plenty of room to spread out and great communal area as well. "
United States
Dan K.
Killington Chalet - Great Space and Location!

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

Killington
8.4 out of 10, Very good, (38)
"Easy access to Killington Mountain "
United States
Dave S.
The price is €253
includes taxes & fees
30 Nov - 1 Dec
Cozy condo on ski shuttle route with free WiFi & full ktichen

Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning

Killington
8.4 out of 10, Very good, (13)
"This was a great location for my family of 6 adults and 2 dogs. 3 bedrooms, 2 bathrooms, hot tub, large indoor area to bring your skis in and store,"
United States
Robin S.
Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ludlow
9.8 out of 10, Exceptional, (127)
"Beautiful place! Enjoyed our stay!"
United States
Cathy B.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Ludlow
10.0 out of 10, Exceptional, (95)
"We had a lovely time. The cabin is cozy and quiet and being on the lake was wonderful. "
United States
Leah C.
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Mount Holly
9.8 out of 10, Exceptional, (225)
"We enjoyed our stay. It’s clean and we weren’t lacking for anything. However those stairs to the 2nd floor are treacherous. "
United States
Laurie H.
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

Ludlow
9.8 out of 10, Exceptional, (40)
"Had a great and comfortable stay with family. House is clean and had all the amenities and supplies needed. "
United States
Aruna G.
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

GREAT WHITE VIEW-SKI ON/SKI OFF-3 Trails HOT TUB & SAUNA- MONTHLY RENTALS

Killington
9.8 out of 10, Exceptional, (57)
"Easy and quick communication with the owner, best location for ski in and out, this is our second time staying at this place for the purpose of location and multiple rooms and four bathrooms, unfortunately I have no comments on the cleanliness of the place, eventhough I have reached out to the owner on the first time we stayed two years ago, please use your imagination !"
United States
Amy x.
GREAT WHITE VIEW-SKI ON/SKI OFF-3 Trails HOT TUB & SAUNA- MONTHLY RENTALS

Winterplace at Okemo

4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (25)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo

Idyllic Lakefront House Suited Two Families

Ludlow
9.6 out of 10, Exceptional, (171)
"House and grounds were well maintained. "
United States
Dorothy Y.
Idyllic Lakefront House Suited Two Families

The Cabin that brings people together

Bridgewater
9.6 out of 10, Exceptional, (82)
"Everyone, including myself, couldn’t help but rave about this place!! It exceeded our expectations from top to bottom. Blown away by how perfect it was and how clean, organized and like every little detail was thought about and considered and it made our stay so comfortable and so fun!!! Definitely would come back next year for our next reunion! "
United States
Stephanie M.
The Cabin that brings people together

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

2.0 star property
Cavendish
10.0 out of 10, Exceptional, (10)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is €309
includes taxes & fees
24 Nov - 25 Nov
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Woodstock
9.8 out of 10, Exceptional, (226)
"Lovely property. Peaceful and beautiful surroundings."
United States
Karen G.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

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

Ludlow
9.8 out of 10, Exceptional, (179)
"Great stay, for a golf trip with 12 guys, there was plenty of room for everyone, would definitely recommend and will be trying to come back and stay as well!"
United States
Matt C.
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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

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, apart-hotels, 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 favorite 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 depends 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 €159 per night. Entering your travel dates in the search wizard you might find 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 45 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 Rutland Country Club.

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.