Vacation rentals in Dragon Hill

5 out of 5 average rating, 10 reviews

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

VanessaRating, 5 stars1 month ago

There is not a shortage of things to do at Anthony's place. The game tables, sauna and hot tub made the weekend really fun, especially for the non skiers of the group. The view from the house is also spectacular! We would definitely rent this place again.

4.99 out of 5 average rating, 120 reviews

Condo in Dover

Winter Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars1 month ago

Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

Superhost

Home in Readsboro

4.86 out of 5 average rating, 125 reviews

Beautiful Vermont! (Pet Friendly)

JudahRating, 5 stars4 months ago

This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

4.78 out of 5 average rating, 163 reviews

Cottage in Becket

Tranquil Lake Cottage on 3 Acres with Large Deck

SarahRating, 5 stars1 week ago

We had a wonderful long weekend at Michelle’s place. We woke to 8 inches of snow in April, so made good use of the fireplace. We enjoyed exploring the area, found several fun places to ride our mountain bikes and showed our daughter another part of Massachusetts away from her college.

4.91 out of 5 average rating, 99 reviews

Tiny home in Whitingham

Cozy Lakeside Tiny Home, Near Skiing

MelissaRating, 5 stars1 month ago

We had a lovely time at this tiny home. It was quiet and relaxing which is exactly what we were looking for. We enjoyed the hot tub and the sunny living room. It was cozy and cute. We took a few trips to Wilmington for food. It’s a cute town. We’d like to come back when the weather is better to enjoy some kayaking and hiking in the area.

4.91 out of 5 average rating, 134 reviews

Apartment in Wilmington

Globetrotter Retreat too - Minutes to the Mountain

XianlongRating, 5 stars4 weeks ago

Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

5 out of 5 average rating, 70 reviews

Cabin in Wilmington

Modern Chalet-private deck/firepit/ clubhouse pool

LoremyRating, 5 stars2 months ago

Michelle and this property are absolute gems. The place is spotless, full of clean and well-maintained pots, pans, kitchen utensils, appliances, and tableware. All the rooms are well appointed and comfortable. We have learned from past rentals that the home is not always cleaned properly. So we normally wipe down all the counters, faucets and tables prior to use. This is the only home that we’ve rented that came away with ZERO dirt. Michelle’s very prompt communication contains very detailed information regarding the house and things to-do around the area. We are in awe of this house and Michelle. We hope that all future renters continue to respect the property so that many more can continue to enjoy it for years to come.

5 out of 5 average rating, 26 reviews

Kiki's Mountain Chateau

DanielRating, 5 stars2 months ago

We highly recommend this house! Great space with everything we needed. The hot tub and fire place was a huge bonus. We had a 4W car and had no trouble driving through the back roads up to the house even during snow/sleet. Stephanie was fantastic- communicated well, helpful, accommodating and a pleasure to rent from.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Dragon Hill vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Dragon Hill

4.95 out of 5 average rating, 42 reviews

Cottage in Woodford

HoneyBear Lake Cottage

CarinaRating, 5 stars8 months ago

We had a wonderful peaceful stay at Honey Bear, Linda Jane is a fantastic host and her home is beautiful and relaxing. It rained a lot of our stay, but we did get to make the most of our stay when it was nice out with all the wonderful inclusions. The boats and games were a fanatic added bonus. Thank you so much

5 out of 5 average rating, 14 reviews

Home in Dover

Mount Snow - Casa Azul

ElizabethRating, 5 stars1 month ago

We had an amazing time! The location was close to the mountain, had god recommendations in the guest book, and Olivia was very responsive and knowledgeable!

4.93 out of 5 average rating, 14 reviews

Home in Monroe

The Camp

BrendaRating, 5 stars2 months ago

We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!

5 out of 5 average rating, 11 reviews

Outdoor Enthusiasts Paradise!

EmilyRating, 5 stars3 months ago

Our family had a beautiful, peaceful ski/snowboard vacation at Samantha’s home. The house was exceptionally clean and Samantha was an attentive host. We’ll hopefully visit again!

4.98 out of 5 average rating, 43 reviews

May Getaway- SOVT -FirePit, Salt HotTub, PETS

JessicaRating, 5 stars1 month ago

Our group of eight people had a wonderful stay at this home, with help from Erika who was in-touch with everything we needed to know. We especially loved the extra bathroom space and two "futon rooms" that offered quiet office/meeting room options as we needed them. The hot tub was beautifully clean as was the rest of the house. Everything we needed- from kitchen appliances to extra blankets- was provided and easy to find. Finally, check-in and out was a breeze thanks to the auto code on the door and clear directions for departure. Many thanks for a great stay!

4.95 out of 5 average rating, 37 reviews

Townhouse in Dover

Beautiful 4 BR Town home minutes from Mt Snow

AriRating, 5 stars1 month ago

John was great - easy and clear communications around how to get in + out of the house. House was well equipped + comfortable. We had a great time Moover bus made skiing extremely convenient as well!

5 out of 5 average rating, 74 reviews

Cabin in Wilmington

Stoni Woods: Log Home in Southern VT

KimberlyRating, 5 stars1 month ago

We’ve stayed at Beth’s place a few times and absolutely love it - hence why we keep coming back and will continue to do so! She is very communicative and her place is squeaky clean and cozy. We love the log cabin feel and want to go back in the summer since we always go in the winter. This was the first time we brought our dog and she was in heaven! Thanks again, Beth!