Luxury
Elevated properties with standout design
Operated by a Wander partner
Trusted operators, vetted by Wander
Note: We kindly ask that you confirm availability with us prior to booking to ensure the best experience.
Tucked into the hillside directly across from Mount Snow, The Overlook Retreat offers a rare blend of mountain access, design integrity, and intentional space, making it equally suited for ski weekends, summer getaways, or family retreats across generations.
The six-bedroom, five-bathroom home was purpose-built for gathering. At its core is an expansive great room with soaring ceilings, a floor-to-ceiling stone fireplace, and windows that flood the space with natural light. The adjoining kitchen is spacious, modern, and made to be used, complete with a double island, high-end appliances, and plenty of room for group meals, late-night snacks, or morning coffee as the mountains wake up.
A large dining table sits at the center of it all, designed to hold the kind of meals that stretch into evenings. Whether you're reconnecting with old friends or watching the kids sprawl out after the slopes, every part of the main level encourages time together, without sacrificing space to breathe.
Just off the great room, a screened-in porch with its own gas fireplace offers a quiet pocket for reading, sipping, or simply watching the weather roll through. Downstairs, a separate lounge space creates room for movie nights, board games, or a little friendly competition, giving different generations their own zones to unwind.
Each bedroom is thoughtfully appointed with natural textures, plush bedding, and just enough simplicity to let the surroundings speak. Bathrooms are modern and spa-like, offering a sense of ease and quiet luxury throughout the home.
Contactless check-in; smart lock access.
Notes & Disclaimers:
Hot Tub and Gym: The hot tub and the Gym available with this rental are located at a clubhouse - a 5 minutes drive away, w/ free pass for guests to access - Thanks!
Wildlife: This is a home in a rural part of the country. You may see wildlife including deer, coyotes, foxes, and bears. Please be mindful of your surroundings and leaving out food and trash.
Weather: In the winter, there will be snow, ice, and occasional snowstorms. We recommend driving a vehicle with AWD or 4WD. Please drive with caution and be prepared with regards to the ability of your vehicle to drive in the snow.
Power & Internet: This is a rural part of the country. You may lose power or internet during inclement weather. We do not issue refunds for loss of power or internet out of our control.
Air conditioning: There's a total of 10 AC units at the house. Each bedroom has one unit (seven in total), and there are three units in the common areas. AC availability is seasonal and depending on weather (late spring and summer). Heating is also seasonal, and depending on weather, available during the cold seasons (autumn - winter).
Pets: We love our furry friends, but this home isn’t set up to host pets. Thanks for understanding and helping us keep the space serene and welcoming for all.
Maximum occupancy: Please mind that this house can host a maximum of 12 guests per fire code. As per the fire department, infants are included in that number. Therefore, any infants included in the booking above maximum occupancy of 12 would unfortunately result in the reservation being cancelled.
Cancellation Policy: We cannot make any exceptions to our cancellation policy. Please consider traveler’s insurance.
Scott
•
October 2025
Dover, Vermont 05356, US
Dover, Vermont, US50% refund up to 60 days before check-in. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
12 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Oct 3, 2026 | $1000 | Available |
| Oct 4, 2026 | $1000 | Available |
| Oct 5, 2026 | $1000 | Available |
| Oct 6, 2026 | $1000 | Available |
| Oct 7, 2026 | $1000 | Available |
| Oct 8, 2026 | $1000 | Available |
| Oct 9, 2026 | $1000 | Available |
| Oct 10, 2026 | $1000 | Available |
| Oct 11, 2026 | $1000 | Available |
| Oct 12, 2026 | $1000 | Available |
| Oct 13, 2026 | $1000 | Available |
| Oct 14, 2026 | $1000 | Available |
| Oct 15, 2026 | $1000 | Available |
| Oct 16, 2026 | $1000 | Available |
| Oct 17, 2026 | $1000 | Available |
| Oct 18, 2026 | $1000 | Available |
| Oct 19, 2026 | $1000 | Available |
| Oct 20, 2026 | $1000 | Available |
| Oct 21, 2026 | $1000 | Available |
| Oct 22, 2026 | $1000 | Available |
| Oct 23, 2026 | $1000 | Available |
| Oct 24, 2026 | $1000 | Available |
| Oct 25, 2026 | $1000 | Available |
| Oct 26, 2026 | $1000 | Available |
| Oct 27, 2026 | $1000 | Available |
| Oct 28, 2026 | $1000 | Available |
| Oct 29, 2026 | $1000 | Available |
| Oct 30, 2026 | $1000 | Available |
| Oct 31, 2026 | $1000 | Available |
| Nov 1, 2026 | $1000 | Available |
| Nov 2, 2026 | $1000 | Available |
| Nov 3, 2026 | $1000 | Available |
| Nov 4, 2026 | $1000 | Available |
| Nov 5, 2026 | $1000 | Available |
| Nov 6, 2026 | $1000 | Available |
| Nov 7, 2026 | $1000 | Available |
| Nov 8, 2026 | $1000 | Available |
| Nov 9, 2026 | $1000 | Available |
| Nov 10, 2026 | $1000 | Available |
| Nov 11, 2026 | $1000 | Available |
| Nov 12, 2026 | $1000 | Available |
| Nov 13, 2026 | $1000 | Available |
| Nov 14, 2026 | $1000 | Available |
| Nov 15, 2026 | $1000 | Available |
| Nov 16, 2026 | $1000 | Available |
| Nov 17, 2026 | $1000 | Available |
| Nov 18, 2026 | $1000 | Available |
| Nov 19, 2026 | $1000 | Available |
| Nov 20, 2026 | $1000 | Available |
| Nov 21, 2026 | $1010 | Available |
| Nov 22, 2026 | $1000 | Available |
| Nov 23, 2026 | $1000 | Available |
| Nov 24, 2026 | $1039 | Available |
| Nov 25, 2026 | $1309 | Available |
| Nov 26, 2026 | $1372 | Available |
| Nov 27, 2026 | $1496 | Available |
| Nov 28, 2026 | $1403 | Available |
| Nov 29, 2026 | $1000 | Available |
| Nov 30, 2026 | $1000 | Available |
| Dec 1, 2026 | $1000 | Available |
| Dec 2, 2026 | $1000 | Available |
| Dec 3, 2026 | $1000 | Available |
| Dec 4, 2026 | $1249 | Available |
| Dec 5, 2026 | $1290 | Available |
| Dec 6, 2026 | $1083 | Available |
| Dec 7, 2026 | $1008 | Available |
| Dec 8, 2026 | $1000 | Available |
| Dec 9, 2026 | $1003 | Available |
| Dec 10, 2026 | $1090 | Available |
| Dec 11, 2026 | $1374 | Available |
| Dec 12, 2026 | $1411 | Available |
| Dec 13, 2026 | $1182 | Available |
| Dec 14, 2026 | $1111 | Available |
| Dec 15, 2026 | $1097 | Available |
| Dec 16, 2026 | $1124 | Available |
| Dec 17, 2026 | $1210 | Available |
| Dec 18, 2026 | $1558 | Available |
| Dec 19, 2026 | $1687 | Available |
| Dec 20, 2026 | $1407 | Available |
| Dec 21, 2026 | $1578 | Available |
| Dec 22, 2026 | $1618 | Available |
| Dec 23, 2026 | $2009 | Available |
| Dec 24, 2026 | $2481 | Available |
| Dec 25, 2026 | $2847 | Available |
| Dec 26, 2026 | $3533 | Available |
| Dec 27, 2026 | $3495 | Available |
| Dec 28, 2026 | $3670 | Available |
| Dec 29, 2026 | $3571 | Available |
| Dec 30, 2026 | $3568 | Available |
| Dec 31, 2026 | $3752 | Available |
| Jan 1, 2027 | $4237 | Available |