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Compare 698 Vacation Homes in Rutland with updated reviews, rates, and availability.

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Living area

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

10.0 out of 10, Exceptional, (93)
"My wife, adult daughter and my wife's parents planned this trip for several months for a leaf tour outside of our home state of PA. We never have visited VT. But have tons of friends that have and recommended a few spots. We wanted to find a spot that would accommodate our 80+ year old parents and their walking limitations and allow us the opportunity to comfortably stay in for the night should we need a break . The location provided a great home-base for our meandering around the state. ...
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Living area

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (88)
"Very comfortable home. Loved the nostalgic feeling "
The price is AED 639
AED 1,392 total
includes taxes & fees
3 Dec - 4 Dec
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Lake

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

9.8 out of 10, Exceptional, (199)
"We had a wonderful 4 days/nights at Cozy Cottage. Perfectly named, well appointed decor and comfortable beds. Perfect for families. The fire pit, kayaks and conoe along with the string lights and sitting areas to watch the wood ducks and beaver family was the perfect way to decompress from the rat race."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Spectacular 4 Bed Killington Home
Exterior

Spectacular 4 Bed Killington Home

9.8 out of 10, Exceptional, (108)
"Great home, abundant firewood, lighting far better than the usual VRBO, lots of cookware, and kind owner. We had an excellent time!"
Spectacular 4 Bed Killington Home
Slopeside Chalet - Ski to and from your home!
Enjoy the views of Bear Mountain directly from the hot tub!

Slopeside Chalet - Ski to and from your home!

10.0 out of 10, Exceptional, (9)
"Exceeded my expectations - luxury bedding - condo felt homey and just smelled good! Hosts very responsive! Best Topridge experience we’ve had"
The price is AED 1,170
AED 3,120 total
includes taxes & fees
2 Dec - 3 Dec
Slopeside Chalet - Ski to and from your home!
Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!
Exterior

Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Had a nice stay with friends at this beautiful house. Very spacious with plenty of beds and bathrooms. Spacious and very clean in quiet, peaceful location. Hosts quickly responded to any questions."
Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Image from trailhead

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

9.8 out of 10, Exceptional, (52)
"This is our second stay at Joel’s condo. His improvements to the lower floor are very nice and made a lot of sense. We enjoyed the location and condo once again. Joel continues to be very thoughtful and helpful. A great place to get away, relax, and have fun. We also got some late season skiing in for those of us who enjoy the slopes."
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

9.2 out of 10, Wonderful, (65)
"Best place to visit for fall leaf peeping! Very enjoyable experience "
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
Okemo Mountain Lodging
Exterior

Okemo Mountain Lodging

3.5 star property
7.6 out of 10, Good, (26)
"I had an amazing time with my family, I will definitely be coming back "
Okemo Mountain Lodging
Luxurious guest home with private art gallery in the heart of a historic village
The Gallery at Six, circa 1880

Luxurious guest home with private art gallery in the heart of a historic village

10.0 out of 10, Exceptional, (13)
"Absolutely unique and amazing experience staying here. Space is gorgeously appointed and impeccably clean. Walk out the door right into a cute town with all the amenities right there. Edward was the perfect host: attentive to detail, communicative and pleasant. We will definitely stay here again if in the area! "
Luxurious guest home with private art gallery in the heart of a historic village
Beautifully renovated with fireplace and coffee bar
Enter the home to an open living space

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (83)
"A lovely, cozy spot in historic Quechee. The hosts have thoughtfully designed the experience in every way - definitely a property I will stay at again when I am in the area!"
Beautifully renovated with fireplace and coffee bar
Custom-built Tiny House on forested lot near Quechee
House facade from driveway

Custom-built Tiny House on forested lot near Quechee

10.0 out of 10, Exceptional, (48)
"Great location, property was beautiful! "
Custom-built Tiny House on forested lot near Quechee
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.8 out of 10, Excellent, (18)
"Very cute cabin in the woods. Less than 2 miles off of route 4, which made it easy to get anywhere in Vermont!"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
The Brandon Inn - King Room
Exterior

The Brandon Inn - King Room

8.4 out of 10, Very Good, (5)
"The Branford Inn was a historic hotel that despite its age was very nice."
The price is AED 569
AED 724 total
includes taxes & fees
26 Nov - 27 Nov
The Brandon Inn - King Room
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Interior

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (63)
"This house was perfect for our group of twelve. We were three families with kids ranging in ages from 6-14yrs old. There was enough space for everyone to relax after a day of skiing. The kitchen was very well stocked and had everything we needed. The ski hill is only a 5 mins drive. We would definitely stay here again"
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Hilltop 9-BR Mountain Retreat 5-min to Okemo
Pool

Hilltop 9-BR Mountain Retreat 5-min to Okemo

Hilltop 9-BR Mountain Retreat 5-min to Okemo
Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding
beautiful fall day at house view from deck

Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding

10.0 out of 10, Exceptional, (54)
"Beautiful fall foliage trip, Woodsy, cozy, private mountain getaway, close to everything house was well located, private, pleasant, well appointed and tastefully decorated, stunning views out the back. Beds and couches very comfortable!!! Hot tub works well. Good vibes overall. we were a party of 2 adults and 2 kids, couldve had 2 more people comfortably, but more than that would have been too much."
Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (74)
"This is my third stay here. It's a wonderful cabin and property for nature lovers! The lovely deck is a perfect place to take in the surroundings. A pond, a waterfall, a fire pit and a cozy cabin, totally private, what more could you ask for? If you have physical limitations, just be aware that you have to walk up a small hill and some stairs from the parking area and the spiral staircase inside may be difficult to navigate for some. "
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

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

9.6 out of 10, Exceptional, (34)
"Great weekend! Beautiful location !!"
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
Located in the Okemo Mt. Community, a mile to the base lodge

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

9.8 out of 10, Exceptional, (164)
"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 "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
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 property types in Rutland

Stunning Wedding & Retreat Venue (19 bedrooms)
Aerial view - 19 bedrooms on 13 acres

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...
The price is AED 19,279
AED 34,472 total
includes taxes & fees
26 Nov - 27 Nov
Stunning Wedding & Retreat Venue (19 bedrooms)
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor spa tub

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
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.