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Browse Select Wilmington Cottages

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cozy cabin with a front entrance and glass doors, surrounded by lush greenery and a stone pathway.

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

8.8 out of 10, Excellent, (53)
"Great place just need the fire place to be fixed asap, especially for the winter time"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Home with a spring-fed pond and mountain view.
Surrounded by dense coniferous trees, this house features a sloped roof and a chimney, with a pathway leading to the entrance.

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (117)
"Cute cottage with a lot of charm. The kiddos loved the concept of staying next to a pond. Convenient location to Manchester center and also to Bromley. Jeremy was quick to respond to all to all pf our questions."
Home with a spring-fed pond and mountain view.
Rare new Home on Lake Whitingham. Semi-priv beach
Situated in a serene winter landscape, this cabin features a cozy front porch and steeply pitched roof.

Rare new Home on Lake Whitingham. Semi-priv beach

10.0 out of 10, Exceptional, (1)
"This home is spectacular, built on a hillside overlooking a pond. Very tastefully built into the landscape. Inside was very well appointed and plenty of room for our family. Three bathrooms was a big plusCould have spent the entire day lookjng out the windows"
Rare new Home on Lake Whitingham. Semi-priv beach
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Situated on a grassy lawn, this charming house features a gabled roof and a welcoming front porch.

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

8.0 out of 10, Very good, (2)
"Definitely not worth the cost of stay. Location was beautiful, but many issues with safety hazards & cleanliness of property.I think most of the pictures speak for themselves. Cleanliness items not pictured were unvacuumed carpet with pet hair, unmade beds & one bed with incomplete linens. Safety items not pictured included multiple soft spots in deck about to rot through (we placed deck furniture over these areas to avoid them) & the outside hose was set to hot water only - a definite burn...
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Lake life at Woodford Cottage
Stylish single-story home with a front door, windows, and a garage, set amidst a lush garden with a barbecue grill and a bench.

Lake life at Woodford Cottage

9.6 out of 10, Exceptional, (15)
"Perfect getaway for a family ski trip."
Lake life at Woodford Cottage
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Escape to a serene retreat surrounded by lush greenery and trees, with a charming single-story house featuring a covered porch and central chimney.

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3.0 star property
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Bennington Gem w/ Smart TV Near Historic District!
House (1 Bedroom) | Front of property

Bennington Gem w/ Smart TV Near Historic District!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
Bennington Gem w/ Smart TV Near Historic District!
Cozy Country Cottage
Perched on stilts, this cabin offers a serene retreat surrounded by lush greenery.

Cozy Country Cottage

10.0 out of 10, Exceptional, (6)
"Absolutely amazing place to stay property owner was so nice and easy to get along with very gorgeous property looking forward to staying again!! "
Cozy Country Cottage
Charlemont Retreat on Chickley River w/ EV Charger
Situated in a wooded area, this charming home offers a front porch with outdoor seating and a chimney.

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Near Hiking & Skiing: Home in Wilmington!
House (3 Bedrooms) | Interior

Near Hiking & Skiing: Home in Wilmington!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
Near Hiking & Skiing: Home in Wilmington!
Near Skiing & Hiking: Quiet Home in West Wardsboro
Cozy cabin with a gabled roof, large windows, and a front door, perfect for a comfortable stay.

Near Skiing & Hiking: Quiet Home in West Wardsboro

3.0 star property
Near Skiing & Hiking: Quiet Home in West Wardsboro
This cottage is a 0 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Set amidst lush greenery, this charming house features a gabled roof and a welcoming porch.

This cottage is a 0 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

10.0 out of 10, Exceptional, (28)
"This was a great location… close to town but also close to skiing, hiking and skating."
This cottage is a 0 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Cozy Wilmington Home: 6 Mi to Mount Snow!
House (4 Bedrooms) | Interior

Cozy Wilmington Home: 6 Mi to Mount Snow!

3.0 star property
Cozy Wilmington Home: 6 Mi to Mount Snow!
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Step into a serene retreat surrounded by a well-maintained lawn and a stone pathway, with a charming single-story building and a covered porch offering a sheltered space for relaxation.

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Escape to a serene natural setting in this charming cabin-style house with a porch and balcony.

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

9.6 out of 10, Exceptional, (64)
"We enjoyed our stay in this cozy cabin on the ridge. The owners have great taste and they have thought of everything to make the stay pleasant. "
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Cavalier Cottage B&B
Exterior

Cavalier Cottage B&B

3.0 star property
9.0 out of 10, Wonderful, (2)
"Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). "
Cavalier Cottage B&B
Perfect for a peaceful get away in clean fresh Vermont air!
Stroll up to the charming entrance, flanked by windows, and enjoy the covered deck area.

Perfect for a peaceful get away in clean fresh Vermont air!

10.0 out of 10, Exceptional, (74)
"Enjoyed the cozy cabin feel. Property was extremely clean and when hit with snow the plow service was totally on top of it! A lovely stay!"
Perfect for a peaceful get away in clean fresh Vermont air!
Luxury Vacation Rental in the Berkshires!
Relax in a serene outdoor setting with a central fire pit surrounded by Adirondack chairs.

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Wilmington Vacation Rental Near Hiking and Skiing!
Guests can enjoy a tranquil outdoor space with a deck, table, and chairs under a canopy, surrounded by lush greenery.

Wilmington Vacation Rental Near Hiking and Skiing!

3.0 star property
Wilmington Vacation Rental Near Hiking and Skiing!
< 6 Mi to Arlington: 'whimsical Stone Abode!'
Cottage (1 Bedroom) | Interior

< 6 Mi to Arlington: 'whimsical Stone Abode!'

3.0 star property
10.0 out of 10, Exceptional, (1)
"We came into town for a few days to visit friends. This was a perfect place. The home was clean and very inviting! Quiet location. Fully stocked kitchen with all the appliances and cooking ware you may need. You will not regret staying here. We loved the photo album of how the home was built! "
< 6 Mi to Arlington: 'whimsical Stone Abode!'
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.
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Top Wilmington Hotel Reviews

The Nutmeg

The Nutmeg

10/10 Excellent
"Wonderful friendly staff and great art/decor! Amazing breakfast!"
Donna 1-night trip
Posted 2 days ago
The Nutmeg