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Compare 469 Vacation Homes in Randolph with updated reviews, rates, and availability.

Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (74)
"We stayed at this cute and well appointed cottage when dropping our son off to Dartmouth. The cottage was clean and very comfortable. The beds were comfortable and the kitchen was very well appointed. It was a breeze to get laundry done in a laundromat right next door. You have to download an app for the laundry to work, but it was straightforward and the same app works at the Dartmouth dorms. Thanks for a wonderful stay. Would recommend to anyone who's looking for a comfortable and...
Beautifully renovated with fireplace and coffee bar
Historic Schoolhouse in Rural Vermont Beauty Spot
10.0 out of 10, Exceptional, (24)
"The schoolhouse was just what we were looking for- a quiet country location with good walking, hiking, exploring, and close to Randolph. We appreciated the ephemera- books, maps, newspapers. Looking through the shelves and cabinets was an adventure unto itself. We spend time outdoors so one plus would have been more comfortable outdoor furniture. Thank you, Terrie, we have a terrific time!"
Historic Schoolhouse in Rural Vermont Beauty Spot
Large, Comfortable, Retro 1970s Hillside Chalet
8.8 out of 10, Excellent, (36)
"Great location with stunning View's. "
Large, Comfortable, Retro 1970s Hillside Chalet
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
10.0 out of 10, Exceptional, (15)
"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
9.2 out of 10, Wonderful, (63)
"This suited us well for a 1 night stay. There were 4 of us. The twin bed I slept in makes noise every time I rolled over, so didn't sleep well. I have stayed in the vicinity before so I expected no cell service upon arrival, so just be aware and print the instructions to enter the home because you may not be able to get in on your phone. It's very small, but perfectly fine for us. I prefer dealing directly with the owner through VRBO instead of all the texts/notifications from Vacasa. That was...
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
HappyCub! Hot tub, game room, fire pit!
10.0 out of 10, Exceptional, (12)
"My husband, son and our friends enjoyed staying at this home. We all slept comfortably and had all of the necessary amenities. Hosts were very proactive and responsive. Appreciated the added touch they provided with the Vermont Maple syrup for our pancakes (I had actually forgot to bring syrup) and coffee. The group was able to enjoy the hot tub each night after a long day of skiing! Will definitely look to stay here again!"
The price is ¥27,809
¥81,678 total
includes taxes & fees
Oct 9 - Oct 10
HappyCub! Hot tub, game room, fire pit!
Cozy private country setting - 15 miles from Woodstock
10.0 out of 10, Exceptional, (20)
"A lovely spot to stay! Great communication with the host!"
Cozy private country setting - 15 miles from Woodstock
Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome.
10.0 out of 10, Exceptional, (17)
"My wife and I stayed for a long weekend along with our dog and thoroughly enjoyed it. It is extremely peaceful and private, there is very little traffic on the road. The owners are very responsive, and Gary was extremely helpful when I had some car trouble on the day we were leaving. Highly recommended!"
The price is ¥25,174
¥45,917 total
includes taxes & fees
Sep 25 - Sep 26
Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome.
Breathtaking Views 7 Bedroom Estate w/Hot Tub
2.0 star property
The price is ¥35,193
¥130,761 total
includes taxes & fees
Sep 29 - Sep 30
Breathtaking Views 7 Bedroom Estate w/Hot Tub
Lovely wooded home with deck, enclosed porch - dog-friendly
7.8 out of 10, Good, (18)
"We enjoyed our stay. It is a beautiful property. The only complaint I have is the TV did not have any good channels. No news channels not cable etc.."
Lovely wooded home with deck, enclosed porch - dog-friendly
Spacious 3-story home near ski area with private hot tub, Ping-Pong
6.8 out of 10, (13)
"Enjoyed our stay. The home was cozy with lots of amenities. "
Spacious 3-story home near ski area with private hot tub, Ping-Pong
☆ SKI ON & OFF ☆ Spruce Glen C on Great Eastern Trail w/AC, Sauna, Fireplace
9.6 out of 10, Exceptional, (60)
"Very comfortable stay. Convenient to Killington, Woodward reservoir, and Woodstock not far away. Great communication. "
☆ SKI ON & OFF ☆ Spruce Glen C on Great Eastern Trail w/AC, Sauna, Fireplace
Spectacular 4 Bed Killington Home
9.8 out of 10, Exceptional, (104)
"Beautiful area with lots to do nearby. Perfect getaway my family and I needed!"
Spectacular 4 Bed Killington Home
Ski house 8 min from the mountain
9.8 out of 10, Exceptional, (14)
"Great time at this place gorgeous view and host was a pleasure to deal with. 👍👍"
Ski house 8 min from the mountain
The Brandon Inn - Fourth Floor Queen Room
9.4 out of 10, Exceptional, (3)
"This is a great spot. Was in town w Gus my field spaniel and we had a nice time at the Inn. The room was a bit antiquated but that’s part of the charm. We hiked the green mountains/silver lake trail and this place was perfect to rest weary bones. The rates are very reasonable and the property is quite beautiful. Will be back! "
The price is ¥20,858
¥26,590 total
includes taxes & fees
Oct 20 - Oct 21
The Brandon Inn - Fourth Floor Queen Room
Beautiful Private Vermont Home 2 minutes to Sugarbush Resort at Mt. Ellen with views of the slopes
10.0 out of 10, Exceptional, (14)
"Excellent home for a family getaway. Clean and as described in listing. Great communication with rental management when needed. Close to swimming and downtown Waitsfield. Drivable to Burlington, Waterbury and Stowe for day trips. Would definitely book again for our family!!!"
Beautiful Private Vermont Home 2 minutes to Sugarbush Resort at Mt. Ellen with views of the slopes
Beautiful New 5-bedroom Home Near Skiing, Hiking, Golf, Weddings, Lake, Foliage
10.0 out of 10, Exceptional, (52)
"Owners were communicative, helpful and you can’t beat this location!! We rented for our wedding at mountaintop … it was perfect !"
Beautiful New 5-bedroom Home Near Skiing, Hiking, Golf, Weddings, Lake, Foliage
Waterfront retreat with dock, sauna, & firepit - near Woodstock & ski areas
10.0 out of 10, Exceptional, (8)
"Beautiful Location and super clean house! We loved being right on the lake and loved the views at sunrise and sunset, especially. Close to Woodstock and the little market right down the street on the corner is perfect for grabbing last minute items or ingredients for a quick dinner. Only issue was the king bed was actually two twin beds pushed together ( that wasn’t very securely put together.) Fun little game room with keyboard and great Wi-Fi."
Waterfront retreat with dock, sauna, & firepit - near Woodstock & ski areas
The Brandon Inn - King Room
9.4 out of 10, Exceptional, (3)
"The room was very comfortable with a huge bathroom. There were two steps up to the tub, which might be difficult for some. Also the jets on the spa tub did not work."
The price is ¥25,174
¥32,043 total
includes taxes & fees
Oct 20 - Oct 21
The Brandon Inn - King Room
Roundabout Ridge
9.2 out of 10, Wonderful, (18)
"A very unique property with plenty of space for family to sleep and some of the best star-gazing views you will ever experience in a private setting. A great spot to "get away from it all" without being too far from basic necessities like grocery stores, restaurants, etc..., and truly a beautiful and interesting place to spend time. The appliances and tech are generally outdated, but usable, and there is wifi and a TV just in case you can't live without it 😉. If you don't mind stairs, and you...
Roundabout Ridge
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Other property types in Randolph

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (462)
"If you’re looking for rest and relaxation this is it. You are one with nature at this cabin which has everything you need. Host was very nice and accommodating. Plenty of yard games for the family and trails to explore. Hope to be back in the future. "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (38)
"Absolutely perfect! Very nice location. Quiet and cozy little townhome. Short drive to Bear Mountain and Killington Ski Resort. Amazing area with plenty of awesome views."
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (209)
"Jeff is a very gracious host and kept in communication throughout this VRBO experience. The cabin is a wonderfully enchanting place with a lot of privacy, and everything you need to make your time spent there a very relaxing and rewarding experience. The cabin is within 20 minutes of Stowe, Vt. The culture is downhome and the food is great!!!!"
Cozy Loft for two with 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.