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Compare 210 Vacation Homes in Roxbury with updated reviews, rates, and availability.

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
Spacious country home, beautiful sunsets, 40 acres
10.0 out of 10, Exceptional, (21)
"Hosts are excellent communicators, and property is accurately described. When I arrived, there was an alarm going off on the stovetop. I didn’t want to bother the host, but I did reach out the following morning, and within minutes, I received a response which immediately solved the problem (reset breaker). This provides an excellent location to visit life-long friends in the area, with the convenience of a great kitchen. (We are already quite familiar with the surrounding area.) The...
Spacious country home, beautiful sunsets, 40 acres
Large multi-family ski home located on the slopes of Sugarbush Resort
9.8 out of 10, Exceptional, (20)
"Great spot for a group or family, convenient location, fully stocked kitchen , plenty of room to spread out, would recommend it for a trip to Sugarbush. Ski in & out is doable with a little effort"
Large multi-family ski home located on the slopes of Sugarbush Resort
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
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
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
Breathtaking Views 7 Bedroom Estate w/Hot Tub
2.0 star property
The price is ¥29,864
¥123,040 total
includes taxes & fees
Sep 29 - Sep 30
Breathtaking Views 7 Bedroom Estate w/Hot Tub
Beautiful 4-Bedroom Home beside Middlebury College
9.6 out of 10, Exceptional, (38)
"We loved our time at this beautiful home. A quaint cottage feel with a beautiful English garden in the back. A short field walk to Middlebury College and just minutes from downtown."
Beautiful 4-Bedroom Home beside Middlebury College
The Brandon Inn - Fourth Floor Queen Room
8.6 out of 10, Excellent, (4)
"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 ¥20,620
¥26,287 total
includes taxes & fees
Oct 20 - Oct 21
The Brandon Inn - Fourth Floor Queen Room
A peaceful & uplifting retreat with AMAZING views in the heart of the mountains.
10.0 out of 10, Exceptional, (89)
"My family, including two young kids, stated at this home above the clouds over the Labor Day weekend. The home was IMMACULATE and had every convenience. The owners were nearby and available, and very communicative leaving us potential itineraries, food recommendations, and overall being very welcoming. I cannot say enough and have never had as gracious a host for a vacation rental. The home was both cozy and had opportunities for separate space if needed. The views were incredible of the...
A peaceful & uplifting retreat with AMAZING views in the heart of the mountains.
Lovely Brookfield Home w/Private Deck & Views
10.0 out of 10, Exceptional, (16)
"My family stayed at Winderlea for 2 nights to attend a family party. This house was absolutely perfect for us! There was so much space & privacy and many places to gather. The house was beautiful and fully equipped with everything we needed. I honestly can't say one negative thing. The property surrounding the home was gorgeous and peaceful. Brian greeted us at the property and was so nice. We give it ☆☆☆☆☆!! furnished and "
Lovely Brookfield Home w/Private Deck & Views
Heart of Vermont Guest House with Family-Friendly Amenities
10.0 out of 10, Exceptional, (5)
"Very pretty house inside and out. Mountain views are amazing. The sheep and pasture are really nice to see. We enjoyed every morning out on the covered porch having coffee and breakfast while taking in the views. The house is centrally located to so many places in Vermont. The pond had nice fishing for kids. Communication was very prompt. I would love to come back to the property next time we come to Vermont. "
Heart of Vermont Guest House with Family-Friendly Amenities
Beautiful Northfield Village Home
10.0 out of 10, Exceptional, (3)
"Check in was very easy, communication was great. We were only there for a short time but we loved the house and how cozy it was and the bedding was our absolute favorite from any of the places we have stayed. Nice neighbors we got to chat with too!!"
Beautiful Northfield Village Home
Sunset Meadow
9.0 out of 10, Wonderful, (2)
"PROs: Communication and check in were quick and easy. The finishes on the interior were very nice, and it was an easy drive off the expressway. The heater warmed the house up quickly. CONs: The floors creaked - a lot.The beds were Purple knock-offs, on a metal frame (no box spring). The master bedroom was directly above the 3rd bedroom and adjacent to the 2nd bedroom. Combine all three of those facts, and, if you're a couple hoping for some quiet Adult Time after the kids go to bed, well, it...
Sunset Meadow
Cozy, updated riverfront home with private hot tub, gas stove & AC
9.0 out of 10, Wonderful, (47)
"Comfortable beds and nice large kitchen. Firepit and hot tub were a plus. We enjoyed walking in the river."
Cozy, updated riverfront home with private hot tub, gas stove & AC
Private Beach on Lake - Five (5) Bedrooms/ Four (4) Bathrooms
10.0 out of 10, Exceptional, (100)
"Nice"
Private Beach on Lake - Five (5) Bedrooms/ Four (4) Bathrooms
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
Dog-friendly forest home on 2.6 acres with hot tub, EV charger & woodstove
7.8 out of 10, Good, (9)
"The property itself is lovely and as advertised, though as other reviews point out, the hot tub is in an enclosed, insulated hut. This trades views of the scenery (which are great, but not from the hot tub) for privacy (which our group enjoyed). What the listing does not say is that the property is approx 3/4 miles up a 7% grade dirt road that is heavily rutted with mud. We made it work, but Vacasa (the property management company) remained very strict on their 10am departure and were unwilling...
Dog-friendly forest home on 2.6 acres with hot tub, EV charger & woodstove
Ellen’s Edge~ Game Room~Home Theater~Hot Tub~Home Gym~
10.0 out of 10, Exceptional, (3)
"The property is beautiful and the host is responsive, thorough, and courteous. This is a great experience not to be missed in the MVR !"
Ellen’s Edge~ Game Room~Home Theater~Hot Tub~Home Gym~
Spacious, dog-friendly house w/ free WiFi, gas fireplace, private grill
9.6 out of 10, Exceptional, (42)
"Clean, convenient to Bolton Valley/Stowe/Smugglers Notch ski areas, very very well stocked and so comfortable. Great sunset views over Camel's Hump. We so appreciate that this property is rentable. Thank you again!"
Spacious, dog-friendly house w/ free WiFi, gas fireplace, private grill
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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 Roxbury

Rustic Roxbury Ski Farmhouse with Trails!
9.6 out of 10, Exceptional, (7)
"Nice rustic farmhouse "
Rustic Roxbury Ski Farmhouse with Trails!
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (464)
"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
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.