
House vacation rentals in Dorset
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Top-rated house rentals in Dorset
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Popular amenities for Dorset house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington
So close to many houses king spots.

Magical Farm Getaway - a must visit!
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

Ranch at Mendon Mt Orchards
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!

Adams Farm-"The Little Farmhouse"
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

SugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.

3BD-Close to Saratoga & Lake George!
Nicole was very friendly and easy to reach, her place was super cozy and beautiful!!! Thank you for the amazing experience:-)

Hollywood Bungalow in the Berkshires #C0191633410
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

Historic 1850’s Renovated Farmhouse w/ Pool!
Beautiful home. Pictures don’t do this location justice. Booked for our daughters wedding being held close by for relatives traveling and ourselves to be close to wedding. Would highly recommend for anyone looking in that area. They have thought of everything you could possibly need. We were out at events more than at the home and I honestly with we had done another day to enjoy some down time in the beautiful home. Owners and local property manager were wonderful at communicating and making sure everything was cared for (we had no concerns, but having contacts if there were any)
Weekly house rentals

25 Rocky Ridge Road: Ski Home for Groups. Hot Tub.
The house was exactly what we were looking for. It was at most 8 minutes from the bottom of the mountain. Super easy to get to and fron everything at Killington. Classically, the first morning we forgot gloves, then skis, then a helmet. Doing the roundtrip from the mountain was easy. The house was exactly as discribed and perfectly appointed for a ski house. Kids loved the foosball table. Kitchen was easy to use and had plenty of fridge space, cooking areas, and seating. The two living rooms allowed people space to decompress differently. Bedrooms were well sized and had plenty of sleeping areas. The hot tube was hot! Simple Vacation was highly responsive and a great host. We couldn't have asked for more. It was exactly what we were looking for and we will be back.

Clean, Captivating VT Farmhouse near Stratton!
Great house, amazing location near Stratton, and Matthew was just great. He was super communicative, and went above and beyond to make sure we were happy with our stay. We'd love to return again.

Near Killington, 7p Hot tub, Mtn. views, Spacious!
This place was beautiful, and so much bigger than the pictures!! We loved how private it felt, and it was just a short walk to downtown! Would recommend to anyone coming to this area, and would gladly stay again ourselves!!

Spring/Summer Fun Treasures Waiting
Great place. Was a bit further from Stratton but close to Manchester and Rutland for food options. It is check in with the hosts - clearly in the instructions - which I overlooked upon booking. The place was just as described and the event brought over blueberry muffins which was a nice touch.

Charming 6 BR home 8 min walk to MassMoca
Nancy was a great host. She was responsive and proactive providing us instructions for accessing the property. The house had lots of space for our group of 9 and it was nice to have a full kitchen to cook in while we stayed. The walk to MOCA was around 15 minutes with our group, which included five kids. It was nice being so close to town. We hope to be back again!

Wilmington A-Frame- Cozy and Convenient
This spot is absolutely perfect to be on a quite spot to enjoy nature but still right within walking distance of the center of Wilmington. The cabin itself is beautifully appointed, gorgeous, and super comfortable. Due to rain we ended up spending most of our time inside relaxing and watching movies, and have zero regrets about it. The host was also extremely friendly, helpful and responsive. I'll definitely be coming back again and recommend this for a Wilmington get away weekend!

Beautiful Vermont Farmhouse with stunning view
We had a wonderful weekend getaway at this unique and charming farm-style property. The house has a cozy and inviting atmosphere, equipped with everything you need for a relaxing stay with family or friends. Located in a peaceful and quiet area, it’s just a short 10-minute drive to town, making it the perfect combination of seclusion and convenience. We stayed here while snowboarding at Killington, and it was a fantastic base for our trip. Susan, the host, made our stay even more memorable with her personal touch. She gave us a warm welcome through a call, providing a quick orientation and offering excellent recommendations for activities and places to visit in the area. Her attention to detail and thoughtfulness truly stood out. Highly recommended for anyone looking for a serene and unique escape!

Mount Snow 5 Star Batwing House Spring Discounts
The Batwing is the perfect spot for a big ski group. Can’t get any more convenient. House was clean and comfortable. Beds were super comfortable. Double sided fireplace was awesome. Hot tub was awesome. Had a great layout and the host was super responsive. Would 100% stay there again.
Private house rentals

Charming Vacation Home in Manchester Center
Steal of a deal for this place. Perfect for any couple or family looking to do a vermont ski vacation. Has all the amenities you need, it’s super spacious, it’s right by town, and it’s a short drive to stratton or bromley. Easy 5 stars.

Country hideaway
Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!

2 Units, 1 Home | Perfect for Multiple Families
The overall experience is good. Just a reminder: the 1st and 2nd floors use separate doors and are not internally connected. However, the location is very close to Okemo and Killington, and the interior decoration is quite good for the price.

Spacious Brattleboro home on river, walk to town
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.

Your VT Dream House: Fireplace, Pool, Dogs
Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.

Morin Manor, spacious home w/fireplace, large yard
It was the second time a group of us stayed at the Manor (9 of us total). It worked out perfectly. Beds are comfortable plenty of space for us all. Kitchen was clean and well stocked with dishes and pans. Along with complementary coffee. Communication is a five star plus!!! Will be back again next year!!

Killington Chalet -Very Close To Slopes!
Went here with a large group of friends for a skiing trip in Killington and the location and house was perfect for what we needed. Herb was extremely responsive to all questions and concerns we had, would absolutely recommend staying here if your a skier/border or are just trying to experience the area with a large group of people!

2 Bedroom House part of duplex in the Village
The staff at The Heritage were outstanding. Ray was god sent, he went above and beyond everyday. Not many left like him.
Quick stats about house rentals in Dorset
Total rentals
50 properties
Nightly prices starting at
$124 CAD before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Stratton Mountain
- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Saratoga Race Course
- Saratoga Spa State Park
- West Mountain Ski Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Pineridge Cross Country Ski Area
- Ekwanok Country Club
- Hooper Golf Course
- Lake George Expedition Park
- Fort Ticonderoga
- National Museum of Racing and Hall of Fame
- Stump Sprouts Ski Touring Center
- Northern Cross Vineyard
- Clarksburg State Park
- Peebles Island State Park
- Hildene, The Lincoln Family Home