The Bennington County Court House with a white facade, green shutters, and a gold dome.

Search Southern Vermont Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Southern Vermont cottages

Exterior

1. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
$456 nightly
The price is $515
Nov 3 - Nov 4
Total with taxes and fees
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

2. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
$271 nightly
The price is $298
Oct 7 - Oct 8
Total with taxes and fees
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A house with a gravel driveway, surrounded by trees and a well-maintained lawn.

3. Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (50 reviews)
"Nice cozy little home Was well welcomed and host very communicative"
United States
Caleb N.
$170 nightly
The price is $189
Oct 6 - Oct 7
Total with taxes and fees
Peaceful Cottage Retreat
A single-story house with a gabled roof, large windows, and a chimney.

4. Quaint, friendly cottage with lakefront location & water views

Quaint, friendly cottage with lakefront location & water views
Poultney
9.4 out of 10, Exceptional, (60 reviews)
"The cottage is in a nice spot on the lake. It is accurately depicted in the listing and was great for our trip"
United States
Jim V.
$385 nightly
The price is $431
Oct 9 - Oct 10
Total with taxes and fees
Quaint, friendly cottage with lakefront location & water views
A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

5. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
$483 nightly
The price is $541
Nov 4 - Nov 5
Total with taxes and fees
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
A row of white houses with a clear night sky and visible stars.

6. Comfy Cottage with Private Hot Tub in Historic East Poultney

Comfy Cottage with Private Hot Tub in Historic East Poultney
Poultney
10.0 out of 10, Exceptional, (16 reviews)
"Very comfortable and clean cottage in a beautiful village. The shower in the bath is incredible. "
United States
Karen C.
$344 nightly
The price is $385
Oct 14 - Oct 15
Total with taxes and fees
Comfy Cottage with Private Hot Tub in Historic East Poultney
A wooden deck with a table and chairs, surrounded by greenery and a wooden fence.

7. Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.4 out of 10, Good, (10 reviews)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
$296 nightly
The price is $321
Oct 12 - Oct 13
Total with taxes and fees
Brook Road Cabin
A wooden deck with picnic tables and chairs, surrounded by dense trees and a clear sky.

8. Hilltop Cottage

Hilltop Cottage
Argyle
10.0 out of 10, Exceptional, (3 reviews)
"great place to stay"
United States
Anna Z.
$789 nightly
The price is $876
Oct 6 - Oct 7
Total with taxes and fees
Hilltop Cottage
A cabin with a wooden deck, a covered porch, and a gravel driveway.

9. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
$499 nightly
The price is $554
Oct 6 - Oct 7
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A green wooden house with a sloped roof and a front porch.

10. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
$1,955 nightly
The price is $2,151
Oct 6 - Oct 7
Total with taxes and fees
Luxe Mountain Home w/ Chefs Kitchen & Okemo 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southern Vermont Hotel Reviews

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Great place to stay"
Joseph 1-night trip
Posted less than an hour ago
The Black Bear Lodge at Stratton Mountain Resort

Find out more about Southern Vermont

Southern Vermont Cottages information

Number of reviews
141
Accommodation
130 Cottages
Lowest Price
$189
Highest Price
$2,151

Frequently asked questions

How much do cottages in Southern Vermont cost?
Prices for cottages in Southern Vermont range between $189 and $2,151 per night. Whatever your budget, you're sure to find the ideal place to reconnect 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?
Explore our 130 cottages in Southern Vermont and lock in your favorite. Whether you're thinking about a vacation with the fam or a weekend with friends, your perfect stay is just a few clicks away with Expedia.
Why book your cottage in Southern Vermont with Expedia?
We think that vacays should be a breeze, so if you're seeking cottages in Southern Vermont at a competitive rate, Expedia has you covered. Stick to the budget and check in to an economical option far from the hustle and bustle, or splurge on a luxury cottage to really pamper your favorite people.
How can I find cheap cottages in Southern Vermont?
The simplest way to spot cheap cottages in Southern Vermont is with Expedia's handy filter tool. Refine your search by budget, amenities and star rating to nab unbeatable deals in just a few keystrokes.
What is there to do in Southern Vermont near my cottage?
You'll find plenty of things to keep you busy in Southern Vermont. If you're bound for Brattleboro, don't miss Creamery Covered Bridge, Vermont Jazz Center and Tasha Tudor Museum. Basing yourself in Manchester Center? Equinox Preservation Trust, Gander Gallery and Manchester Designer Outlets are popular sights in this city.

Explore a world of travel with Expedia