Woodstock, VT Vacation Homes from AED 851

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

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

AED 1,573 total

includes taxes & fees

25 Oct - 26 Oct

A large house with a fire pit and outdoor seating.

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

Bridgewater

Susan S.

AED 1,995 total

includes taxes & fees

4 Nov - 5 Nov

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

3. 180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

Hartford

Anthony A.

AED 2,171 total

includes taxes & fees

25 Oct - 26 Oct

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

4. Luxury Condo Tucked in the Heart of Killington

Killington

"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...

Melinda D.

AED 1,092 total

includes taxes & fees

3 Nov - 4 Nov

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

12 Oct - 13 Oct

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

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

Killington

AED 3,789 total

includes taxes & fees

13 Oct - 14 Oct

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

Killington

Gregg Z.

AED 2,266 total

includes taxes & fees

15 Oct - 16 Oct

A cabin with a deck, a hot tub, and a fire pit area.

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

Killington

AED 2,711 total

includes taxes & fees

26 Oct - 27 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.

9. CozyDen- Location, Ski Off/ Shuttle On

Killington

Berni H.

AED 1,115 total

includes taxes & fees

21 Oct - 22 Oct

A hot tub in a lush garden with a wooden deck and stairs leading to a cabin.

10. Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

Killington

Briana S.

AED 2,381 total

includes taxes & fees

11 Oct - 12 Oct

A covered porch with a grill, two Adirondack chairs, and a fire pit.

11. Estelle Cottage- Pool, hot tub, Fireplace

The Woods

"Yes!! King beds!! Tall people love king beds and they delivered. This does not diminish the fact that everything was excellent for our stay. From the welcome gifts including some great local coffee and syrup, to the relaxing sauna, the comfortable large living room and bedrooms, and all amenities, we wanted for nothing. Truly a gem on our whole vacation! We looked forward to returning in the late afternoon knowing we had a quiet evening and a good sleep ahead of us. Truly a great place to...

Devin

AED 2,578 total

includes taxes & fees

4 Nov - 5 Nov

A wooden interior with a bench and shelves, a door with a handle, and a tiled floor.

12. The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals

Killington

Gifford F.

AED 1,886 total

includes taxes & fees

14 Oct - 15 Oct

A forested area with a wooden structure and a red and blue playset.

13. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

Killington

Matthew P.

A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

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

Mendon

Aurore H.

AED 851 total

includes taxes & fees

1 Nov - 2 Nov

A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

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

Killington

Patrick B.

AED 2,702 total

includes taxes & fees

13 Oct - 14 Oct

A spacious living area with a fireplace, a television, and a dining area with natural light.

16. Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Killington

Ron L.

AED 2,379 total

includes taxes & fees

12 Oct - 13 Oct

A spacious kitchen with a central island, wooden ceiling, and large windows.

17. Hot Tub Getaway - Near Killington - Sleeps 12

Killington

wesley s.

AED 3,715 total

includes taxes & fees

14 Oct - 15 Oct

A cozy living room with a fireplace, a sofa set, and a stone wall.

18. Bearmont- Pool, HotTub, Fireplace

The Woods

Tyler B.

AED 2,421 total

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with dark wood cabinets, a stainless steel refrigerator, a dining table with chairs, and a hanging light fixture.

19. Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals

Killington

Sandra G.

AED 2,463 total

includes taxes & fees

14 Oct - 15 Oct

A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

20. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

North Sherburne

"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...

Essa R.

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Top Woodstock Hotel Reviews

Align Inn Vermont

8/10 Good

"Y"

On The River Inn

10/10 Excellent

"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."

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."

Room 1

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

4. Luxury Condo Tucked in the Heart of Killington

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

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

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

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

9. CozyDen- Location, Ski Off/ Shuttle On

10. Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

11. Estelle Cottage- Pool, hot tub, Fireplace

12. The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals

13. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

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

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

16. Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

17. Hot Tub Getaway - Near Killington - Sleeps 12

18. Bearmont- Pool, HotTub, Fireplace

19. Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals

20. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Find vacation rentals that suit your style

Top Woodstock Hotel Reviews

Align Inn Vermont

The Mountain Inn at Killington

Fireside Inn & Suites West Lebanon

Comfort Inn Rutland - Killington

Lincoln Inn & Gallery

The Shire Woodstock

On The River Inn

The Vesper

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

4. Luxury Condo Tucked in the Heart of Killington

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

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

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

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

9. CozyDen- Location, Ski Off/ Shuttle On

10. Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

11. Estelle Cottage- Pool, hot tub, Fireplace

12. The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals

13. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

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

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

16. Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

17. Hot Tub Getaway - Near Killington - Sleeps 12

18. Bearmont- Pool, HotTub, Fireplace

19. Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals

20. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Find vacation rentals that suit your style

Top Woodstock Hotel Reviews

Align Inn Vermont