A winding road surrounded by autumn foliage.

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In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Rutland cottages

A wooden deck with a lattice railing overlooking a dense forest.

1. The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.6 out of 10, Exceptional, (24 reviews)
"The communication with Host was awesome to a question we had; Dave's response was so helpful. Beautiful place, quiet. Get ‘get-away’."
United States
Diane
$402 nightly
The price is $521
Nov 15 - Nov 16
Total with taxes and fees
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
A wooden deck with potted yellow flowers and a small wooden structure with a colorful mural.

2. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (97 reviews)
"The cottage was just lovely. Very comfortable. And the host was really nice and helpful. A wonderful stay!"
United States
Laura Ann
$167 nightly
The price is $187
Nov 15 - Nov 16
Total with taxes and fees
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
A white building with green shutters and a small porch, surrounded by autumn foliage and a clear sky.

3. 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, (18 reviews)
"Very comfortable and clean cottage in a beautiful village. The shower in the bath is incredible. "
United States
Karen C.
$342 nightly
The price is $383
Nov 16 - Nov 17
Total with taxes and fees
Comfy Cottage with Private Hot Tub in Historic East Poultney
A wooden deck with two chairs and a small table, overlooking a green landscape.

4. Game Room, Fire Pit & Views! Spacious Ludlow Home

Game Room, Fire Pit & Views! Spacious Ludlow Home
3.0 star property
Ludlow
$719 nightly
The price is $791
Nov 15 - Nov 16
Total with taxes and fees
Game Room, Fire Pit & Views! Spacious Ludlow Home
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 6

Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
Cavendish
10.0 out of 10, Exceptional, (4 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
$492 nightly
The price is $551
Nov 15 - Nov 16
Total with taxes and fees
Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
A two-story house with a green exterior and orange trim, surrounded by snow.

6. 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
Nov 15 - Nov 16
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.
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Top Rutland Hotel Reviews

The Shire Woodstock

The Shire Woodstock

8/10 Good
"Property was in a good location. Very pretty. No tissues in bathroom. Tv did not work. The whole time we were there it had “No service” it read on screen. That wouldn’t have been an issue because I also had an iPad and iphone but the WiFi was sketchy at best."
Amy 1-night trip
Posted 19 hours ago
The Shire Woodstock

Find out more about Rutland

Rutland Cottages information

Number of reviews
143
Accommodation
97 Cottages
Lowest Price
$187
Highest Price
$2,151

Frequently asked questions

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Expedia has some great cottages in Rutland, so get set for an unforgettable vacation on nature's doorstep. If you're sticking to a budget, select how much you're willing to spend and the preferred star rating of your property. Or, make your way to the filters to search for cottages with a pool or a hot tub. We'll help you find the perfect place whatever your escape looks like.
How can I find cheap cottages in Rutland?
An excellent way to get cheap cottages in Rutland is with Expedia's useful filter tool. Refine your search by star rating, budget and amenities to secure awesome rates with only a few clicks.
What is there to do in Rutland near my cottage?
Whatever you love to do, Rutland has plenty to keep you busy. Rutland Country Club, Paramount Theater and Vermont State Fairgrounds are on many travelers' schedules. Don't leave without exploring Diamond Run Mall, Pine Hill Park and Green Mountain Rock Climbing Center either. With Expedia's Rutland hotel deals, you can discover even more terrific attractions like these with the cash you save.

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