Chimney Hill - Wilmington, VT Vacation Rentals

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Make Chimney Hill - Wilmington, VT your next getaway

Chimney Hill is a private mountain community in southern Vermont near Wilmington, known for wooded surroundings, a quiet cabin-in-the-pines feel, and easy access to the Mount Snow area. It’s a great home base if you want a peaceful place to recharge after days spent exploring nearby lakes, trails, and small-town stops.

Explore Chimney Hill - Wilmington, VT house rentals, cabins, and more

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House rentals

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Cabins

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Chimney Hill - Wilmington, VT vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Snow Country Home
3 Bed | 2 Bath | Sleeps 6

Snow Country Home - Wilmington, VT

$199 avg / night
(excludes fees and taxes)
3.69 (16)
Log Ski Lodge
1 Bed | 2 Bath | Sleeps 6

Log Ski Lodge - Wilmington, VT

$193 avg / night
(excludes fees and taxes)
3.56 (18)
Chimney Hill Retreat
3 Bed | 2 Bath | Sleeps 6

Chimney Hill Retreat - Wilmington, VT

$353 avg / night
(excludes fees and taxes)
4.33 (3)
Greer Court Retreat
3 Bed | 1.5 Bath | Sleeps 6

Greer Court Retreat - Wilmington, VT

$350 avg / night
(excludes fees and taxes)
5.0 (1)
Deck & Game Room: Family Wilmington Retreat
5 Bed | 4 Bath | Sleeps 10

Deck & Game Room: Family Wilmington Retreat - Wilmington, VT

$890 avg / night
(excludes fees and taxes)
4.0 (4)

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Recent Chimney Hill - Wilmington, VT vacation rental reviews

The cabin was clean, comfortable Our family truly enjoyed our stay
Donna Marie G. | Mar 2026
The house was so cozy and truly had everything we needed for our little ski trip. It was close enough to Mount Snow but also really nice and secluded and quiet at the same time. Everything was very clean and had everything we need. Would definitely come back
Angelica . | Feb 2026
We stayed at The Cozy Bear Cabin for a ski weekend with friends, and it was the perfect place to stay. The cabin is tucked away on a quiet cul-de-sac with a beautiful, private backyard, which made it feel peaceful and relaxing. It was cozy, very clean, and fully stocked with everything we needed for the weekend. The location was ideal, just a short drive to the ski mountain, making it easy to go back and forth throughout the day if needed. The bedrooms were a great, and the beds were incredibly comfortable. Overall, we had a wonderful weekend at The Cozy Bear Cabin and would absolutely stay here again. Highly recommend!
Randy . | Feb 2026
Chimney Hill - Wilmington, VT Frequently Asked Questions

Yes, 6 of our Chimney Hill - Wilmington, VT homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 11 of our Chimney Hill - Wilmington, VT vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Chimney Hill - Wilmington, VT vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Chimney Hill - Wilmington, VT team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Chimney Hill - Wilmington, VT, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Why visit Chimney Hill in Vermont

Chimney Hill offers the kind of Vermont stay many travelers picture: evergreen forests, winding roads, and cozy homes that feel removed—without being far from restaurants, groceries, and year-round attractions. Located just outside Wilmington, it’s especially convenient for trips that mix quiet evenings at your rental with day trips to Mount Snow, Harriman Reservoir (Lake Whitingham), and local shops and cafés.

It’s also a solid choice for groups and families who want shared amenities in a community setting. Many rentals have features like fireplaces, decks, and space to spread out, while the neighborhood amenities add extra options when you want something close to home.

Best time to visit Chimney Hill in Vermont and what weather to expect

Winter (December–March) is prime time if you’re coming for snow season in the Mount Snow region. Expect cold temperatures, frequent snow events, and icy conditions on shaded roads—plan for true winter driving. Days can be bright and crisp, while nights often drop well below freezing.

Summer (late June–August) brings warm days and cooler nights, with comfortable mountain air and plenty of greenery. Afternoon storms are possible, so it helps to have a flexible plan.

Fall (September–October) is a standout season for foliage, lower humidity, and quieter midweek stays. Temperatures can swing from warm afternoons to chilly evenings, especially later in October. Spring (April–May) is the mud season shoulder period—expect soft ground, variable weather, and occasional lingering snow at higher elevations.

Top things to do in Chimney Hill

Local tips for visiting Chimney Hill

Chimney Hill access and arrival: Mountain roads, parking and winter driving

Chimney Hill’s roads are hilly and can be narrow in spots, which is part of the mountain-community experience. In snow season, conditions can change quickly—plowing schedules, packed snow, and ice are common. If you’re visiting in winter, all-wheel drive or four-wheel drive is strongly recommended, and snow tires make a noticeable difference.

Check your rental listing for parking notes before you arrive. Some homes have steep driveways, limited turnaround space, or designated spots. If you’re traveling with multiple vehicles, confirm how many cars can park comfortably and whether roadside parking is permitted.

Chimney Hill community rules, amenities, and what guests commonly miss

Chimney Hill is a residential community with shared spaces, posted rules, and seasonal operations. Amenity access can depend on the time of year, scheduled hours, and capacity limits. Review the details provided with your booking for what’s included, what requires passes or registration, and any quiet-hour policies.

Guests are often surprised by how much a few small logistics can matter in a mountain rental. Bring what you need for everyday comfort—especially in winter—and plan for limited immediate services once you’re up the hill.