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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Our top choices for Rutland holiday homes

Water front home with large two tiered deck! 2 bathrooms 😂
Property grounds

Water front home with large two tiered deck! 2 bathrooms 😂

9.4 out of 10, Exceptional, (105)
"My family has stayed here 2 weekends and it was perfect for us. Great location and perfect area to relax. Our dog enjoyed swimming and we enjoyed fishing. Great communication with manager also. Look forward to staying here again!"
Water front home with large two tiered deck! 2 bathrooms 😂
Idyllic Lakefront House Suited Two Families
Property grounds

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (163)
"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"
Idyllic Lakefront House Suited Two Families
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Property grounds

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (38)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Converted Carriage Barn | The Carriage House Unit1
Dining

Converted Carriage Barn | The Carriage House Unit1

9.8 out of 10, Exceptional, (21)
"Charming, comfortable, beautiful place. Felt like home and was everything you could want from a converted barn in Vermont!"
Converted Carriage Barn | The Carriage House Unit1
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Exterior

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

9.8 out of 10, Exceptional, (175)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Cottage on east side of Lake Bomoseen, on-site boat slip included
Outdoor dining

Cottage on east side of Lake Bomoseen, on-site boat slip included

9.4 out of 10, Exceptional, (12)
"We enjoyed out stay here and will be coming back."
Cottage on east side of Lake Bomoseen, on-site boat slip included
Custom-built Tiny House on forested lot near Quechee
Fridge, microwave, oven, stovetop

Custom-built Tiny House on forested lot near Quechee

9.8 out of 10, Exceptional, (60)
"Arturo and John are incredibly thoughtful and attentive hosts. They have considered every possible need and detail in the space. It’s beautiful, homey, and full of personality. The hot tub is a dream. We loved the location. It was easily to get to Woodstock, restaurants, and sightseeing, while still feeling remote and secluded. 10/10 would stay here again! "
Custom-built Tiny House on forested lot near Quechee
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Terrace/patio

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

2.0 star property
9.8 out of 10, Exceptional, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Beautifully renovated with fireplace and coffee bar
Smart TV, fireplace, books

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (114)
"Very cozy, great kitchen. The beds are extremely comfortable. The surrounding area is beautiful with plenty to do. Highly recommend."
Beautifully renovated with fireplace and coffee bar
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Fridge, microwave, oven, stovetop

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (55)
"Margarete and Alice welcomed us upon arrival. The house was the quintessential New England home! It was super clean, our bed was very comfortable with soft welcoming linens. The views are incredible, and the property provided much needed peace and tranquility. The weather was not the best but we managed to find plenty to do in the area. Alice, Margarete's black lab, took us for a hike on the property. She was an excellent playful guide! We look forward to returning to this peaceful retreat in...
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Ski Chalet with Hot Tub on Okemo Mountain
Outdoor spa tub

Ski Chalet with Hot Tub on Okemo Mountain

10.0 out of 10, Exceptional, (44)
"Wonderful House - Held 2 Families Perfectly3 min drive to mountain The hot tub is great addition "
Ski Chalet with Hot Tub on Okemo Mountain
Converted Carriage Barn | The Carriage House Unit2
Interior

Converted Carriage Barn | The Carriage House Unit2

9.6 out of 10, Exceptional, (4)
"Very cool conversion of an old barn. Very comfy and rather iconic. Because of the barn construction, there was an occasional encounter with a bug or two. Nicely located with many shops and restaurants nearby. The surrounding neighborhood of Quechee is very pleasant and kind of upscale country. Be aware there are no hangers/closets/ironing board/washer/dryer, so plan accordingly."
Converted Carriage Barn | The Carriage House Unit2
104 Two Queen Bed Standard Hotel Room outdoor heated pool
Property grounds

104 Two Queen Bed Standard Hotel Room outdoor heated pool

8.6 out of 10, Excellent, (27)
"Excellent customer service and beautiful, well-maintained property."
The price is HK$812
HK$1,230 total
includes taxes & fees
25 Aug - 26 Aug
104 Two Queen Bed Standard Hotel Room outdoor heated pool
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms
Terrace/patio

Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

10.0 out of 10, Exceptional, (16)
"It was a wonderful stay in a beautiful home close to all of the places we wanted to spend time!"
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms
Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola
Smart TV, fireplace

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Fridge, microwave, oven, stovetop

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"Absolutely loved it!!! Amazing house. Will definitely stay again!"
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
Exterior

NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

10.0 out of 10, Exceptional, (36)
"Our annual trip was great! The house was fantastic and the owners were very friendly and responsive. Would definitely recommend this awesome house!"
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Exterior

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

9.8 out of 10, Exceptional, (126)
"Terrific and comfortable place to stay! Amazing firepit!"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
Exterior

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

9.8 out of 10, Exceptional, (37)
"Great property, cozy and well maintained!"
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Fridge, microwave, oven, stovetop

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

8.0 out of 10, Very good, (40)
"This place was great for my family and I. It is very close to Okemo and town "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
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

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

10/10 Excellent
"Very accommodating. We use this location for biking and it’s clean and comfortable. The pool is nice also."
Derek 1-night trip
Posted 2 days ago
Comfort Inn Rutland - Killington