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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Featured Cottages in Southern Vermont

Bennington Gem w/ Smart TV Near Historic District!
Private kitchen

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!
Hike & Swim On-site: Cozy Falls Brook Cabin
Interior

Hike & Swim On-site: Cozy Falls Brook Cabin

3.0 star property
10.0 out of 10, Exceptional, (1)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
Hike & Swim On-site: Cozy Falls Brook Cabin
'john's Farmhouse in Mount Snow' on 120 Acres!
5 bedrooms, laptop workspace, free cots/infant beds, bed sheets

'john's Farmhouse in Mount Snow' on 120 Acres!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home. Great for a family get away. Hosts were top notch. I stay in rentals all the time for work and this was great. I will bring my grand kids next time. "
'john's Farmhouse in Mount Snow' on 120 Acres!
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Private kitchen

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Manchester Center Home w/ Green Mtn Views!
Interior

Manchester Center Home w/ Green Mtn Views!

3.0 star property
Manchester Center Home w/ Green Mtn Views!
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
TV, video game console, ping pong, books

Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Charming Putney Home: Porch, Grill & Hiking Trails
Interior

Charming Putney Home: Porch, Grill & Hiking Trails

3.0 star property
Charming Putney Home: Porch, Grill & Hiking Trails
Near Skiing & Hiking: Quiet Home in West Wardsboro
Interior

Near Skiing & Hiking: Quiet Home in West Wardsboro

3.0 star property
Near Skiing & Hiking: Quiet Home in West Wardsboro
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Interior

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Jacksonville Cabin w/ Wraparound Deck & Views
Interior

Jacksonville Cabin w/ Wraparound Deck & Views

3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Spacious Home Near Bromley Mountain Ski Resort!
Exterior

Spacious Home Near Bromley Mountain Ski Resort!

3.0 star property
Spacious Home Near Bromley Mountain Ski Resort!
Wilmington Retreat Near Trails, Skiing & Festivals
Interior

Wilmington Retreat Near Trails, Skiing & Festivals

3.0 star property
10.0 out of 10, Exceptional, (1)
"Would definitely recommend! House had an everything we would need. So comfy and cozy! "
Wilmington Retreat Near Trails, Skiing & Festivals
Near Hiking & Skiing: Home in Wilmington!
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!
Historic New Hampshire Home: 1 Mi to Boat Launch
Interior

Historic New Hampshire Home: 1 Mi to Boat Launch

3.0 star property
Historic New Hampshire Home: 1 Mi to Boat Launch
Londonderry Chalet w/ Deck, Fire Pit & Views!
Dining

Londonderry Chalet w/ Deck, Fire Pit & Views!

3.0 star property
Londonderry Chalet w/ Deck, Fire Pit & Views!
Wilmington Vacation Rental Near Hiking and Skiing!
TV, fireplace, books

Wilmington Vacation Rental Near Hiking and Skiing!

3.0 star property
Wilmington Vacation Rental Near Hiking and Skiing!
Cozy 'green Mountain Chalet' in Putney Town
Coffee/tea maker, paper towels

Cozy 'green Mountain Chalet' in Putney Town

3.0 star property
Cozy 'green Mountain Chalet' in Putney Town
Londonderry Retreat ~ 3 Mi to Lowell Lake!
Outdoor spa tub

Londonderry Retreat ~ 3 Mi to Lowell Lake!

3.0 star property
Londonderry Retreat ~ 3 Mi to Lowell Lake!
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
TV, fireplace

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Enchanting Dorset Mountain Home w/ Stunning Views!
Fireplace

Enchanting Dorset Mountain Home w/ Stunning Views!

3.0 star property
6.0 out of 10, (1)
"The property was clean but run down compared to online photos. It would be helpful to have supplies such as wastebaskets in bathrooms, hand towels, dish clothes, pot holders, juice glasses/cups, extra towels, and paper towels and/or tissues. "
Enchanting Dorset Mountain Home w/ Stunning Views!
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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Other property types in Southern Vermont

Long Trail House at Stratton Mountain Resort
Pool

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is S$653
includes taxes & fees
24 Mar - 25 Mar
Long Trail House at Stratton Mountain Resort
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.

Frequently asked questions

How much do cottages in Southern Vermont cost?
Prices for cottages in Southern Vermont range between and per night. Whatever your budget, you’re sure to find a perfect place to get reacquainted with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Southern Vermont?
Look up our 84 cottages in Southern Vermont and then book your favourite. Whether you’re dreaming of a family holiday or a break with buddies, your perfect stay is just clicks away with Expedia.
Why book your cottage in Southern Vermont with Expedia?
Booking a cottage in Southern Vermont is as simple as entering your travel dates and picking an ideal place for outdoor recreation and relaxation. From upmarket retreats to budget-friendly properties and cottages that come with amenities like laundry facilities, Expedia has something for all tastes and styles. As for unbeatable deals? We’ve got your back!
How can I find cheap cottages in Southern Vermont?
A good way to find cheap cottages in Southern Vermont is with Expedia’s convenient filter tool. Refine your search results by amenities, budget and star rating to land unbeatable rates in a couple of clicks.
What is there to do in Southern Vermont near my cottage?
The best accessory to take on your Southern Vermont getaway is an epic itinerary! Brattleboro Bowl, Brattleboro Museum & Art Centre and Fort Dummer State Park are among the most popular things to do if you’re off to Brattleboro. Bennington also offers lots of terrific attractions, such as Old First Congregational Church. Want to explore more? Make sure you visit Norman Rockwell Exhibition and Robert Frost Stone House Museum too.