Woodstock, VT Cottages from SAR 556

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Our top choices for Woodstock cottages

A white house with a red roof and a hammock in the yard.

1. Addie's Place: A Quiet and Quirky Guesthouse

Hartford

Victor R.

SAR 925 total

includes taxes & fees

15 Nov - 16 Nov

A cabin with a porch, a garage, and a dirt driveway surrounded by trees.

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

Mendon

Diane

SAR 1,705 total

includes taxes & fees

15 Nov - 16 Nov

A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

3. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

Cavendish

Mark G.

SAR 2,152 total

includes taxes & fees

14 Nov - 15 Nov

A wooden deck with two chairs and a small table, overlooking a green landscape.

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

Ludlow

SAR 2,969 total

includes taxes & fees

15 Nov - 16 Nov

A green wooden house with a sloped roof and a front porch.

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

Ludlow

SAR 8,071 total

includes taxes & fees

14 Nov - 15 Nov

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Learn more about Woodstock

Covered bridges and maple syrup farms dot the landscape around this quintessential New England village with its picture-perfect town green. Visit Billings Farm to see Vermont dairy traditions, then browse local artisan shops before hiking nearby Mount Tom for valley views.

See all hotels in Woodstock

A wooden covered bridge with a sign reading 'Slippery When Wet' and a sign above the entrance that says 'Michael's Bridge.'

Top reviews in Woodstock

A two-story house with a porch, American flags, and a well-maintained garden.

The Jackson

West Woodstock

10/10 Excellent

Tiffany

A row of cabins with a river in the foreground, surrounded by trees and a snowy landscape.

Sleep Woodstock Motel

Woodstock

10/10 Excellent

We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...

John

Snowed Inn

Killington

10/10 Excellent

Tammy

A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.

Woodstock Inn & Resort

Woodstock

10/10 Excellent

Anonymous traveler

A wooden dock with two Adirondack chairs and a blanket, overlooking a calm lake with dense forest in the background.

Mountain Meadows Lodge

Killington

10/10 Excellent

Timothy

A two-story house with a balcony, surrounded by lush greenery and a pond.

On The River Inn

West Woodstock

10/10 Excellent

Ayleen

A brick building with a covered patio area, a large tree, and a sign indicating no parking.

The Common Man Inn & Restaurant

Claremont

10/10 Excellent

Robert

A hotel with multiple buildings, a parking area, and a sign indicating availability.

Après Inn Killington

Killington

10/10 Excellent

Anonymous traveler

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

Main and Mountain Bar & Motel

Ludlow

10/10 Excellent

Anonymous traveler

A large, multi-story building with a prominent tower and a covered porch area.

Norwich Inn

Norwich

10/10 Excellent

This historic hotel is amazing. I like to stay here during the off rate part of the week and plan my trips around room availability. Liked Room 28 in the original building. Very cool and I have to remark on the cleanliness of the bed coverings and pillows. Smelled like they were dried outside on a sunshiny day. Wonderful. Like the lady who checked me in, great sense of humor and made me feel welcome. Would stay here again and again.

Ernie

A multi-story hotel with a brick facade, large windows, and a flagpole with an American flag.

Six South St Hotel

Hanover

10/10 Excellent

Lynn

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Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Woodstock cottages

1. Addie's Place: A Quiet and Quirky Guesthouse

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

3. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

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

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

Learn more about Woodstock

Top reviews in Woodstock

The Jackson

10/10 Excellent

Frequently Asked Questions

Why book your cottage in Woodstock with Expedia?

How can I find cheap cottages in Woodstock?