Book Holiday Homes in Wilmington

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Wilmington

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

Winhall
Located in Bondville, this vacation home is on the waterfront, within a 15-minute drive of Green Mountain National Forest and Winhall River.
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful River Retreat

Guilford
When you stay at this vacation home in Brattleboro, you'll be on the waterfront and 7 minutes by car from Green River Wildlife Management Area.
The Jelly Mill-A Peaceful River Retreat
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

Winhall
With a stay at this vacation home in Bondville, you'll be within a 10-minute drive of Stratton Mountain Resort and Green Mountain National Forest.
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!
Save an average of 15% on thousands of hotels when you're signed in
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

Sandgate
Located in Arlington, this vacation home is on a river, within a 15-minute drive of Green Mountain National Forest and Battenkill River.
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown
Located in Williamstown, this vacation home is within a 5-minute drive of Williams College Taconic Golf Course and Williams College.
Contemporary Berkshire Home with Views of Taconic Golf Course
Manchester,  Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Sunderland
With a stay at this vacation home in Arlington, you'll be in the mountains, just steps from Green Mountain National Forest and a 4-minute drive from Mount ...
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Private Family Estate for any Season

Private Family Estate for any Season

West Dover
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 10-minute drive of Mount Snow and Green Mountain National Forest.
Private Family Estate for any Season
Shelburne Falls #1 Rated STR.  Blue on South. Style design with comfort..

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

Buckland
With a stay at this vacation home, you'll be centrally located in Shelburne Falls, just a 3-minute walk from Deerfield River and 9 minutes by foot from Lamson ...
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Whitingham
Located in Whitingham, this vacation home is on the waterfront, within a 15-minute walk of Harriman Reservoir and Green Mountain National Forest.
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Don't see what you're looking for?
See all available properties in Wilmington
View all properties
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.

Wilmington Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Wilmington vacation homes are the perfect way for you to wing it.

Holiday houses in Wilmington let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Wilmington in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Wilmington adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Wilmington with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Wilmington vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Wilmington Holiday Homes essential information

Accommodation
734 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond, The Jelly Mill-A Peaceful River Retreat, 8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!, Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester, Contemporary Berkshire Home with Views of Taconic Golf Course, Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing, Private Family Estate for any Season, Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort.., Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Top trending hotels in Wilmington

Valley Craft Ales

Valley Craft Ales

2 out of 5
18 N Main St, Wilmington, VT
Fully refundableReserve now, pay when you stay
Located in Wilmington, Valley Craft Ales is in the historical district, a 4-minute drive from Harriman Reservoir and 6 minutes from Molly Stark State Park.
Valley Craft Ales
The White House Inn

The White House Inn

3.5 out of 5
178 Route 9 East, Wilmington, VT
Located in Wilmington, The White House Inn is a 2-minute drive from Jim McGrath Gallery and Studio and 9 minutes from Jacksonville Pond.
The White House Inn
The Nutmeg

The Nutmeg

3.5 out of 5
153 West Main St, Wilmington, VT
With a stay at The Nutmeg in Wilmington, you'll be on a river, just a 1-minute walk from North Branch Deerfield River and 8 minutes by foot from Green Mountain ...
The Nutmeg
Save an average of 15% on thousands of hotels when you're signed in
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Wilmington
With a stay at this cottage in Wilmington, you'll be near the beach, just a 1-minute walk from Lake Raponda and 12 minutes by foot from The Art of Humor ...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Don't see what you're looking for?
See all available properties in Wilmington
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.