Photo by Killington Resort

Search Vacation Homes in Rutland

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Homes in Rutland

Vacation Home in Mendon

2.0 star property
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 SAR 687
SAR 1,816 total
includes taxes & fees
1 Dec - 2 Dec
large ski ranch hot tub close to killington pets ok

Vacation Home in Rutland

3.5 star property
The price is SAR 664
SAR 2,195 total
includes taxes & fees
8 Dec - 9 Dec
Rutland's Hidden Gem: 2 Br/1ba Renovated Home Close To Everything 2 Bedroom Home

Vacation Home in Rutland

10.0 out of 10, Exceptional, (1)
The price is SAR 1,358
SAR 2,429 total
includes taxes & fees
14 Dec - 15 Dec
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Vacation Home in Rutland

9.2 out of 10, Wonderful, (5)
"Big and spacious. "
United States
Robert S.
The price is SAR 809
SAR 2,380 total
includes taxes & fees
1 Dec - 2 Dec
Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.

Vacation Home in Mendon

2.0 star property
The price is SAR 1,044
SAR 3,388 total
includes taxes & fees
1 Dec - 2 Dec
Bear Paw Cabin: 3 Living Areas, Hot Tub & Chef's Kitchen 5 Mins to Pico

Vacation Home in Rutland

8.8 out of 10, Excellent, (10)
"Very clean and lovely! Location was perfect! Will be using again. "
United States
Kacy L.
The price is SAR 508
SAR 1,286 total
includes taxes & fees
1 Dec - 2 Dec
Rutland's Hidden Gem: 2 BR/1BA Renovated Home Close to Everything

Vacation Home in Mendon

8.0 out of 10, Very Good, (1)
"It was a beautiful property! So Spacious, kitchen more than completely stocked with anything you’d need! Setting outside amazing! Communication with property so easy and accommodating. What upset me was the downstairs 2 bedrooms were NOT air condtioned and the rooms were SO hot that our daughter didn’t sleep well because of it and in fact one night was kept awake until 4 am because she was so hot!! I didn’t learn about these conditions ( because they did’t complain about it to us)until the night...
United States
Laurie T.
The price is SAR 879
SAR 3,715 total
includes taxes & fees
1 Dec - 2 Dec
Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.

Vacation Home in Mendon

10.0 out of 10, Exceptional, (2)
"The cabin was great and well taken care of. The location was superb!"
United States
Juan P.
The price is SAR 2,063
SAR 5,396 total
includes taxes & fees
15 Dec - 16 Dec
Cortina Mountain Chalet - Outdoor Hot Tub - Close to Pico and Killington Mountains

Vacation Home in Rutland

3.0 star property
The price is SAR 1,177
SAR 3,488 total
includes taxes & fees
1 Dec - 2 Dec
Forest Mountain Escape: Beautiful Mountaintop Escape In Mendon, Vt. 20 Min To Killington/14 To Pico. 4 Bedroom Home

Vacation Home in Rutland

2.0 star property
The price is SAR 2,575
SAR 5,547 total
includes taxes & fees
15 Dec - 16 Dec
Cortina Mountain Chalet - Outdoor Hot Tub - Close To Pico And Killington Mountains 3 Bedroom Home

Vacation Home in Cavendish

9.8 out of 10, Exceptional, (7)
"Just as described with Everything we needed. Very comfy and roomy. Loved the private feeling and backyard. Would highly recommend to anyone wanting to stay in this area of Vermont."
United States
deborah m.
The price is SAR 591
SAR 1,040 total
includes taxes & fees
1 Dec - 2 Dec
Charming Cavendish Guesthouse

Vacation Home in West Windsor

10.0 out of 10, Exceptional, (30)
"Very relaxing house, we all enjoyed the fireplaces and pellet stove and the well-equipped kitchen allowed us to cook beautiful meals. The property is gorgeous and neighbors are far away. This was the perfect place for a friends reunion/ski trip!"
United States
Roy S.
The price is SAR 763
SAR 1,825 total
includes taxes & fees
2 Dec - 3 Dec
Beautiful home offering privacy on 7 acres with private pond

Vacation Home in Cavendish

9.6 out of 10, Exceptional, (4)
"We had an enjoyable stay! Our hosts were very communicative and thought of the details for our stay!"
United States
Maya T.
The price is SAR 574
SAR 1,092 total
includes taxes & fees
1 Dec - 2 Dec
The Dorothy-10 minutes from Okemo- freshly renovated

Vacation Home in Bridgewater

9.6 out of 10, Exceptional, (17)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is SAR 645
SAR 2,025 total
includes taxes & fees
1 Dec - 2 Dec
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Vacation Home in Killington

10.0 out of 10, Exceptional, (1)
"Very quiet and private feeling even though it is in a condo like setting. Very clean, and had all the conveniences we needed (A/C, coffee maker, full kitchen appliances). And so kind and personal to leave some souvenirs of the area. We felt very comfortable when every we finished our day of sightseeing to come back to our home away from home. "
United States
denise k.
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Vacation Home in Killington

8.0 out of 10, Very Good, (1)
"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...
United States
Dean
The price is SAR 446
SAR 1,227 total
includes taxes & fees
1 Dec - 2 Dec
Luxury Condo Tucked in the Heart of Killington

Vacation Home in North Sherburne

3.0 star property
The price is SAR 497
SAR 1,979 total
includes taxes & fees
4 Dec - 5 Dec
Bob's Sled Lodge 2 Bedroom Home

Vacation Home in Pomfret

10.0 out of 10, Exceptional, (4)
"Enjoyed the cleanliness and the convenience of being close to Woodstock, and not too far from Stowe."
United States
Dee Dee H.
The price is SAR 563
SAR 1,424 total
includes taxes & fees
11 Dec - 12 Dec
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Vacation Home in Bomoseen

2.0 star property
9.6 out of 10, Exceptional, (4)
"Nice place to stay. Very well equipped and clean."
United States
Rich S.
The price is SAR 631
SAR 1,999 total
includes taxes & fees
1 Dec - 2 Dec
The Bomoseen Bungalow: Vermont Lake House with Private Dock

Vacation Home in Ludlow

9.8 out of 10, Exceptional, (103)
"A lovely time enjoying the off-season in a ski town. "
United States
Ed C.
The price is SAR 724
SAR 1,534 total
includes taxes & fees
1 Dec - 2 Dec
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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.

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

Top Rutland Hotel Reviews