Woodstock, VT Vacation Homes from AED 697

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Our top choices for Woodstock vacation homes

A cozy living room with a sectional sofa, a fireplace, a flat-screen TV, and a bookshelf.

1. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

Hartford

Joann

A large house with a fire pit and outdoor seating.

2. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Bridgewater

Susan S.

AED 2,020 total

includes taxes & fees

1 Nov - 2 Nov

A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

3. Luxury Condo Tucked in the Heart of Killington

Killington

AED 1,083 total

includes taxes & fees

28 Oct - 29 Oct

A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

4. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Bridgewater

Kathryn F.

AED 2,586 total

includes taxes & fees

5 Oct - 6 Oct

A compact kitchen with a refrigerator, stove, microwave, and sink.

5. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

Plymouth

AED 2,093 total

includes taxes & fees

5 Oct - 6 Oct

A room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

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

Hartford

Anthony A.

AED 2,171 total

includes taxes & fees

26 Oct - 27 Oct

A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

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

Killington

AED 3,549 total

includes taxes & fees

6 Oct - 7 Oct

A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

8. CozyDen- Location, Fireplace, Ski Off/ Shuttle On

Killington

Berni H.

AED 1,103 total

includes taxes & fees

5 Oct - 6 Oct

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Top Woodstock Hotel Reviews

Align Inn Vermont

8/10 Good

"Great location for the Quechee Gorge"

The Shire Woodstock

10/10 Excellent

"We had Deluxe King River view - deluxe has a fireplace and shares a balcony with rocking chairs. The room was great except a couple little maintenance issues (I told the front desk and hope they fix). And it’s a great location walkable to downtown, great views of river and hills, and the inn has fire pits ready to go. Too bad coffee makers are in the hallway, not in the room, and there’s no breakfast (they said they might start next year). We went nearby for breakfast, and a good market is just across the street."

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!"

On The River Inn

8/10 Good

"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."

Woodstock Village Carriage House

8/10 Good

"Great location, the unit was simple, allowed us to walk to town and the grocery store.The only confusion was the outdoor space. Property is beautiful, we were unsure if we could sit by a pool on the property as that was not listed in the marketing material. As a result, we did not find any outdoor space that we could enjoy."

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Check prices for these dates

Our top choices for Woodstock vacation homes

1. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

2. Pet Friendly | Game Room | Minutes to Woodstock and Killington

3. Luxury Condo Tucked in the Heart of Killington

4. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

5. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

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

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

8. CozyDen- Location, Fireplace, Ski Off/ Shuttle On

9. Fall Getaway Near Killington with Hot Tub

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

11. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

12. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

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

14. Cozy Rutland Retreat

15. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

16. Family and friend friendly upper ski cabin with bunks, sleeps 8

17. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

18. The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

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

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

Find vacation rentals that suit your style

Top Woodstock Hotel Reviews

Align Inn Vermont

The Jackson

Fireside Inn & Suites West Lebanon

The Shire Woodstock

Jackson Gore Village, A Vail Resorts Property

On The River Inn

The Vesper

Lincoln Inn & Gallery

Woodstock Village Carriage House

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. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

2. Pet Friendly | Game Room | Minutes to Woodstock and Killington

3. Luxury Condo Tucked in the Heart of Killington

4. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

5. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

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

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

8. CozyDen- Location, Fireplace, Ski Off/ Shuttle On

9. Fall Getaway Near Killington with Hot Tub

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

11. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

12. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

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

14. Cozy Rutland Retreat

15. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

16. Family and friend friendly upper ski cabin with bunks, sleeps 8

17. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

18. The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

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

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

Find vacation rentals that suit your style

Top Woodstock Hotel Reviews

Align Inn Vermont