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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Cottages in Rutland

Our top choices for Rutland cottages

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
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Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place "
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Orwell Cabin on Sunrise Lake w/ Private Dock & BBQ
Terrace/patio

Orwell Cabin on Sunrise Lake w/ Private Dock & BBQ

3.0 star property
10.0 out of 10, Exceptional, (1)
" Great property!! Very nice place everything you need you can find in this home from cookware to glassware, baking needs.. i was reading lot's of reviews about this property and was worried , poor wifi, low water pressure.. i had none of those problems with 7 people total in the home.. Only thing i could say is this mattresses can use an upgrade .. but I'd definitely come back again especially in The summer.. this place must be amazing!! In the winter 4 by 4 is a must have...
Orwell Cabin on Sunrise Lake w/ Private Dock & BBQ
Luxury Vermont Vacation Rental: Private Hot Tub!
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Luxury Vermont Vacation Rental: Private Hot Tub!

3.0 star property
Luxury Vermont Vacation Rental: Private Hot Tub!
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
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Chester Farmhouse on 100 Acres, 15 Min to Okemo!

3.0 star property
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Lakefront Paradise Near Okemo & Killington
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Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
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Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Cozy Castleton Cabin With Fire Pit + Water Access!
Dining

Cozy Castleton Cabin With Fire Pit + Water Access!

3.0 star property
Cozy Castleton Cabin With Fire Pit + Water Access!
Idyllic Wallingford Retreat - Near Skiing & Hiking
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Idyllic Wallingford Retreat - Near Skiing & Hiking

3.0 star property
8.0 out of 10, Very good, (2)
"This was the perfect place for 2 people to stay for a trip to Okemo. Everything we could have needed was available on the property, it was very clean and comfortable, and the hostess was great at communicating details ahead of time. Thanks for allowing us to use your property - I would love to return!"
Idyllic Wallingford Retreat - Near Skiing & Hiking
Inviting Vermont Home On Mount Ascutney!
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Inviting Vermont Home On Mount Ascutney!

3.0 star property
Inviting Vermont Home On Mount Ascutney!
Killington Area Escape w/ Deck, Views & Hot Tub!
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Killington Area Escape w/ Deck, Views & Hot Tub!

3.0 star property
Killington Area Escape w/ Deck, Views & Hot Tub!
Weston Vacation Rental - Close to Ski Resorts!
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Weston Vacation Rental - Close to Ski Resorts!

3.0 star property
Weston Vacation Rental - Close to Ski Resorts!
5 Mi to Skiing: Home w/ Hot Tub & Patio!
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5 Mi to Skiing: Home w/ Hot Tub & Patio!

3.0 star property
5 Mi to Skiing: Home w/ Hot Tub & Patio!
Waterfront Home on Lake Champlain w/ Dock & Kayaks
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Waterfront Home on Lake Champlain w/ Dock & Kayaks

3.0 star property
Waterfront Home on Lake Champlain w/ Dock & Kayaks
Swim, Ski & Sip: Lakefront Retreat in Plymouth
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Swim, Ski & Sip: Lakefront Retreat in Plymouth

3.0 star property
Swim, Ski & Sip: Lakefront Retreat in Plymouth
Walk to Ski Trails: Ludlow Home on Okemo Mountain!
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Walk to Ski Trails: Ludlow Home on Okemo Mountain!

3.0 star property
Walk to Ski Trails: Ludlow Home on Okemo Mountain!
Paddle, Swim & Hike: Family Lake House in Vermont
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Paddle, Swim & Hike: Family Lake House in Vermont

3.0 star property
Paddle, Swim & Hike: Family Lake House in Vermont
Renovated Farmhouse < 1 Mile to Okemo Mountain!
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Renovated Farmhouse < 1 Mile to Okemo Mountain!

3.0 star property
Renovated Farmhouse < 1 Mile to Okemo Mountain!
Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!
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Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!

3.0 star property
Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!
Chic Brandon Cabin w/ Pool, Hot Tub + Sauna!
Dining

Chic Brandon Cabin w/ Pool, Hot Tub + Sauna!

3.0 star property
Chic Brandon Cabin w/ Pool, Hot Tub + Sauna!
Cozy Okemo Cabin: Steps to Lake, 2 Mi to Slopes!
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Cozy Okemo Cabin: Steps to Lake, 2 Mi to Slopes!

3.0 star property
Cozy Okemo Cabin: Steps to Lake, 2 Mi to Slopes!
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 Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"The hotel is very nice, very friendly, beautiful views specially from the room with balcony. Game room is awesome and the breakfast was delicious. Will come back again. "
DANIEL 2-night trip
Posted 20 hours ago
The Mountain Inn at Killington

Frequently asked questions

Why book your cottage in Rutland with Expedia?
Expedia has some great cottages in Rutland, so get set for an unforgettable holiday 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 Theatre and Vermont State Fairgrounds are on many travellers' schedules. Don't leave without exploring Diamond Run Mall, Pine Hill Park and Green Mountain Rock Climbing Centre either. With Expedia's Rutland hotel deals, you can discover even more terrific attractions like these with the cash you save.