Wilmington Vacation Homes

A street with a red brick building and a white building with green shutters. There are flower boxes on the sidewalk.

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Our top choices for Wilmington holiday homes

A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

1. MtSnow* HotTub* Pool * AirHockeyPingPong Darts

Wilmington

HK$5,085 total

includes taxes & fees

21 Oct - 22 Oct

A cozy interior with a wooden ceiling, a large window, and a table with chairs.

2. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Wilmington

Natalie

HK$4,491 total

includes taxes & fees

21 Oct - 22 Oct

A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

3. Walk To Town, Hottub, Firepit, Games, Mt Snow

Wilmington

Jeremy P.

A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

4. The Eagles Wing at The CHM - Private Apartment

Dover

Ava M.

HK$1,490 total

includes taxes & fees

23 Oct - 24 Oct

A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

5. Modern Mount Snow Gnarvana - Steps to Carinthia

Dover

Lynn B.

HK$3,282 total

includes taxes & fees

21 Oct - 22 Oct

An aerial view of a house surrounded by a forest with autumn foliage.

6. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Whitingham

Jonathan

HK$4,026 total

includes taxes & fees

2 Nov - 3 Nov

A bedroom with a bed, bedside tables, a window, and a radiator.

7. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Woodford

Dana W.

HK$3,293 total

includes taxes & fees

21 Oct - 22 Oct

A wooden barrel structure with a staircase and railing, surrounded by a forest.

8. 10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK

Dover

Connor S.

HK$5,368 total

includes taxes & fees

16 Nov - 17 Nov

A pathway through a forest with autumn leaves and a wooden bridge.

9. Experience Vermont’s Fall Magic at here at the Lemondrop

Dover

Alexander H.

HK$5,161 total

includes taxes & fees

21 Oct - 22 Oct

A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

10. Cozy Vermont Tiny Home Get Away

Brattleboro

HK$816 total

includes taxes & fees

4 Nov - 5 Nov

A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

11. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Dover

jim f.

HK$9,254 total

includes taxes & fees

21 Oct - 22 Oct

A two-story house with a porch, surrounded by trees and snow.

12. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Bennington

Malika R.

HK$3,064 total

includes taxes & fees

23 Oct - 24 Oct

A modern interior with large windows, a wooden ceiling, and a cozy seating area.

13. Stunning Glass House nestled in the Vermont wilderness!

Guilford

Chris O.

HK$3,986 total

includes taxes & fees

8 Nov - 9 Nov

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

14. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton

HK$2,010 total

includes taxes & fees

25 Oct - 26 Oct

A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

15. Greylock Cabin

Florida

Margaret M.

HK$3,600 total

includes taxes & fees

17 Nov - 18 Nov

A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

16. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

HK$1,622 total

includes taxes & fees

9 Nov - 10 Nov

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

17. Cozy Home in Pownal VT

Pownal

Jeri R.

HK$1,609 total

includes taxes & fees

21 Oct - 22 Oct

A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

18. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

Stratton

Brian G.

HK$8,680 total

includes taxes & fees

9 Nov - 10 Nov

A kitchen with white cabinets, a wooden dining table, and pendant lights.

19. A roomy remodeled retreat close to MassMoCA

North Adams

Diane

HK$3,778 total

includes taxes & fees

20 Nov - 21 Nov

A garden with a wooden pergola, purple flowers, and a river view.

20. Family Friendly Hilltop House In Putney Vermont

Putney

Susan G.

HK$2,051 total

includes taxes & fees

28 Oct - 29 Oct

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Top Wilmington Hotel Reviews

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent

"The hotel was built in the 1990’s per the concierge, which surprised us, as it is so well maintained that it seems much newer! We booked a king bed room with (small) balcony. Our only complaint would be the bathroom toilet situation. Toilet is very small and way too close to the door…a very awkward setup, especially trying to get into the shower. The tub and shower however seemed completely new. Very nice! The room is quite large and the bed was very comfortable. I’m only 4’10” so it was a high hurdle for me, so I made up the couch bed and slept there. I usually bring a small folding stool but forgot it, so the couch bed was a nice option…it seems to be new and was comfortable. The first night we ate at the hotel restaurant and everything was very tasty, especially the Brussel sprouts and salmon. We were celebrating my husband’s birthday weekend, and brought wine but had to drink from coffee mugs as the hotel is “green” so no cups in the room. We snagged a couple cups from the restaurant for our second night. 😊 Also there’s no mini fridge. We had breakfast twice at 1MTN restaurant, which we highly recommend! Second night we had dinner at “Ten Tables”…their Berkshire Pork Chop was PHENOMENAL. 3rd night we drove down to Wilmington to “The Anchor”…every single thing was delicious! We had a superb weekend!"

Hideaway Inn Mt. Snow

8/10 Good

"It was a tablet check in which was fairly easy but sends the room number and access code to your e mail address . The rooms were clean and tidy. Free hot drinks in an area on a lower floor. Check out didn’t work on the tablet, so used the telephone. Nobody answered that call, but a member of staff appeared and said everything was fine and we could leave. Diving distance to local restaurants and there were numerous. The gondola was close by, although we didn’t go to the top because it was raining hard and didn’t think we would see much."

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