Stockbridge Holiday Houses

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Our top choices for Stockbridge holiday homes

A wooden deck with Adirondack chairs and a table, overlooking a mountainous landscape.

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

Stockbridge

Kevin M.

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a large window, a bed with a wooden headboard, two bedside tables, and a ceiling fan.

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

Stockbridge

Sophie L.

includes taxes & fees

8 Nov - 9 Nov

A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

3. 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.

includes taxes & fees

8 Nov - 9 Nov

A covered porch with a view of a white house and a green lawn.

4. 150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!

Bethel

Jamie R.

includes taxes & fees

8 Nov - 9 Nov

An indoor swimming pool with a wooden ceiling and large windows.

Killington

wesley s.

includes taxes & fees

8 Nov - 9 Nov

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

includes taxes & fees

9 Nov - 10 Nov

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

12. Bearmont- Pool, HotTub, Fireplace

The Woods

Tyler B.

includes taxes & fees

9 Nov - 10 Nov

A cabin with a wooden deck, surrounded by lush greenery and a garden with purple flowers.

13. Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

Killington

Catherine S.

includes taxes & fees

8 Nov - 9 Nov

A two-story wooden cabin with a balcony, illuminated windows, and a front door.

14. BearRight- Pool, Hot Tub, Sauna

Killington

Kevin F.

includes taxes & fees

7 Nov - 8 Nov

A modern kitchen with a wooden dining table, metal chairs, and a hanging light fixture.

15. BearAll - Both Units of Duplex on Killington Road!

Killington

Colin S.

includes taxes & fees

8 Nov - 9 Nov

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

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

Mendon

Aurore H.

includes taxes & fees

12 Nov - 13 Nov

An outdoor seating area with red chairs and a fire pit, surrounded by a gravel path and string lights.

17. DoubleDen Upper- Fireplace, Hot tub, Views!

Killington

A modern kitchen with a dishwasher, a coffee maker, and a dining area with a wooden table set for two.

18. Cozy Rutland Retreat

Rutland

Susan E.

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a wooden bed, a patterned rug, a nightstand with a lamp, and a small shelf with books.

19. Kingsley Homestead - 2 Bedroom retreat

Rutland

includes taxes & fees

7 Nov - 8 Nov

A kitchen with granite countertops, stainless steel appliances, wooden cabinets, and a large island with seating.

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

Killington

includes taxes & fees

8 Nov - 9 Nov

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Top Stockbridge Hotel Reviews

On The River Inn

10/10 Excellent

"We loved our spacious room, the sauna, pool/hot tub and game room! We were welcomed with a s’mores pack and spent the evening by the cozy fire pit. Lovely hotel!"

Emrose Luxury Cabins

8/10 Good

"The cabins are new and well maintained. There are pots and pans and spatulas but incredibly no coffee maker. I don’t believe I’ve ever stayed in a room at any price point without a coffee maker. Also, the bed is up against a wall so you have to choose who has to crawl in and out of the bed to go to the bathroom, get a glass of water, etc. Not fun. There was also no contact information for management, so when we couldn’t figure out how to get the heater or fireplace working, we had to chat with Hotels.com who claimed our room did not have heat. Really? Vermont in the fall? Are you kidding me? After I almost lost my mind, they had someone from hotel management call me and instruct me how to turn the heat on. He was very nice and solved the problem, but how about providing contact information of someone on premises if there is an issue? The place is fairly new, and I like the concept, but they have a few things to iron out before they are ready for prime time. Let’s start with an $25 coffee maker in every room. Is that too much to ask? And Hotels.com really needs to get their chat proficiency together…."

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews	137
Accommodation	704 Holiday Homes
Lowest Price	NZ$285
Highest Price	NZ$2,632

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Check prices for these dates

Our top choices for Stockbridge holiday homes

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

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

3. Luxury Condo Tucked in the Heart of Killington

4. 150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!

5. The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

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

7. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

8. SnowArts, Wood Burning fireplace, Close to slopes

9. CozyDen- Fireplace, Ski Off/ Shuttle On

10. Hot Tub Getaway - Near Killington - Sleeps 12