Woodstock, VT Vacation Homes from ￥30,143

A red convertible car parked in front of a brick house with black shutters and a white picket fence.

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Our top choices for Woodstock vacation homes

1. Upper Sunny Side Suite Near Quechee, VT shops and restaurants.

White River junction

￥30,374 total

includes taxes & fees

Sep 28 - Sep 29

2. Beautiful 3-bedroom house with AC in charming Bridgewater

Bridgewater

Susan S.

￥84,016 total

includes taxes & fees

Sep 23 - Sep 24

Coffee/tea maker, fridge, microwave, oven

3. Luxury Condo Tucked in the Heart of Killington

Killington

￥43,942 total

includes taxes & fees

Sep 23 - Sep 24

4. Stunning Views, 10 Mins from Woodstock

Pomfret

￥132,800 total

includes taxes & fees

Oct 5 - Oct 6

5. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Killington

￥154,891 total

includes taxes & fees

Sep 20 - Sep 21

6. 180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

Hartford

Anthony A.

￥83,813 total

includes taxes & fees

Sep 20 - Sep 21

7. CozyDen - AC, Bike to Mountain, Porch!

Killington

Berni H.

￥42,559 total

includes taxes & fees

Sep 24 - Sep 25

8. Breathtaking Riverfront Farmhouse w/Mountain Views

Bridgewater

Matthew V.

￥140,283 total

includes taxes & fees

Oct 5 - Oct 6

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Top Woodstock Hotel Reviews

The Jackson

10/10 Excellent

"Love staying in this beautiful hotel had very comfy beds and made us feel like we were in the heart of New England"

Woodstock Inn & Resort

8/10 Good

"Woodstock itself is absolutely beautiful and has a wonderful atmosphere. However, we had a few issues in both common areas, and our room that significantly impacted our experience. First, the cleanliness of the lobby was disappointing. I noticed that it was noticeably dusty and had visible spiderwebs in several areas, which did not create a welcoming first impression. Second, the bathroom and bed did not live up to the luxurious standard expected. Both the bathroom sink and bathtub drained incredibly slowly. This resulted in an unpleasant backflow of water whenever I tried to use them, which felt very unhygienic. Lastly, the bed was lopsided and very uncomfortable. The boxspring on both sides of the bed was covered in stains, which took away from the charm and comfort of the room. Everything else was great, and with a little more attention to room cleanliness, this place would be flawless."

Hotel Coolidge

8/10 Good

"This is a very old hotel on the national historic record. Because of that the doors and floors creak and the floors slope. The bathroom has older fixtures but work fine. Our room was actually two rooms; one with a queen bed and one with a small couch and sink. Both rooms had TVs. We had a small fridge. Bed was comfortable. They had an elevator that was very slow but since we had heavy items we were very grateful for it. The stairway and moldings were beautiful. If you enjoy historic architecture you will appreciate this hotel. The parking seemed a bit sketchy but was actually fine. They had a fireplace and a Keurig in lobby so tea, coffee and hot chocolate available 24/7. Also had vouchers for discounts at neighboring breakfast sites. They are dog friendly, but only for specified rooms. They also had a refundable $100 charge for any damage done due to the dog. There was a $25 charge for the dog which is pretty standard. All in all it was a fine place to stay."

Hilton Garden Inn Hanover Lebanon

10/10 Excellent

"To be clear, this isn't a five-star hotel, but it was an excellent stay--the property was clean, quiet, and pretty new. The bed was comfortable, wifi was stable, and HVAC worked just fine. I didn't try most of the amenities so can't answer to that. If I had any negatives, one of the elevators was down during my three-day stay. And the location isn't ideal if you're looking to be near something walkable. Totally recommend for a clean and quiet stay."

Find out more about Woodstock

Woodstock Vacation Homes information

Number of reviews	96
Accommodation	859 Vacation Homes
Lowest Price	￥30,143
Highest Price	￥142,415

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Woodstock vacation homes

1. Upper Sunny Side Suite Near Quechee, VT shops and restaurants.

2. Beautiful 3-bedroom house with AC in charming Bridgewater

3. Luxury Condo Tucked in the Heart of Killington

4. Stunning Views, 10 Mins from Woodstock

5. Slopeside Estate Guesthouse: Hot tub, AC, Grill

6. 180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

7. CozyDen - AC, Bike to Mountain, Porch!

8. Breathtaking Riverfront Farmhouse w/Mountain Views

9. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

10. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

11. Ski Home/Arcade Mountain Views Near Killington/Woodstock

12. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

13. Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!

14. New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds

15. Cozy Rutland Retreat

16. New Ludlow Village Home with Stunning Okemo Mountain View

17. Hot Tub Getaway - Near Killington - Sleeps 12

18. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

19. Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails

20. The Tower House | Hot Tub | Firepit | Dog-Friendly

Find vacation rentals that suit your style

Top Woodstock Hotel Reviews

The Jackson

Mountain Meadows Lodge

Woodstock Inn & Resort

Hotel Coolidge

Hilton Garden Inn Hanover Lebanon

On The River Inn

The Mountain Inn at Killington

Lincoln Inn & Gallery

The Shire Woodstock

Find out more about Woodstock

Woodstock Vacation Homes information

Explore a world of travel with Expedia

Search Vacation Homes in Woodstock

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Woodstock vacation homes

1. Upper Sunny Side Suite Near Quechee, VT shops and restaurants.

2. Beautiful 3-bedroom house with AC in charming Bridgewater

3. Luxury Condo Tucked in the Heart of Killington

4. Stunning Views, 10 Mins from Woodstock

5. Slopeside Estate Guesthouse: Hot tub, AC, Grill

6. 180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

7. CozyDen - AC, Bike to Mountain, Porch!

8. Breathtaking Riverfront Farmhouse w/Mountain Views

9. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

10. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

11. Ski Home/Arcade Mountain Views Near Killington/Woodstock

12. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

13. Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!

14. New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds

15. Cozy Rutland Retreat

16. New Ludlow Village Home with Stunning Okemo Mountain View

17. Hot Tub Getaway - Near Killington - Sleeps 12

18. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

19. Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails

20. The Tower House | Hot Tub | Firepit | Dog-Friendly

Find vacation rentals that suit your style

Top Woodstock Hotel Reviews

The Jackson

Find out more about Woodstock

Woodstock Vacation Homes information

Explore a world of travel with Expedia