Chittenden Holiday Houses

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Our top choices for Chittenden holiday homes

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

1. Cozy Rutland Retreat

Rutland

Susan E.

includes taxes & fees

9 Nov - 10 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.

2. 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

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 house with a wooden deck, solar panels, and a well-maintained garden.

4. Kingsley Homestead - 2 Bedroom retreat

Rutland

includes taxes & fees

9 Nov - 10 Nov

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

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

Stockbridge

Kevin M.

includes taxes & fees

8 Nov - 9 Nov

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

Stockbridge

Sophie L.

includes taxes & fees

8 Nov - 9 Nov

A house with a covered deck, a barbecue grill, and a wooden pergola.

7. large ski ranch hot tub close to killington pets ok

Mendon

Callison A.

includes taxes & fees

17 Nov - 18 Nov

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

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

Killington

Patrick B.

includes taxes & fees

8 Nov - 9 Nov

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

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

The Woods

includes taxes & fees

8 Nov - 9 Nov

A stone fireplace with a black mantel, framed picture, and decorative items.

10. SnowArts, Wood Burning fireplace, Close to slopes

Killington

Tammy W.

A rustic cabin with a stone fire pit, wooden deck, and a chimney.

11. Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.

Mendon

Heidi S.

includes taxes & fees

8 Nov - 9 Nov

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.

12. CozyDen- Fireplace, Ski Off/ Shuttle On

Killington

Berni H.

includes taxes & fees

8 Nov - 9 Nov

A spacious living room with a sofa, coffee table, and fireplace. There is a large window providing a view of the outdoors.

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

Killington

Matthew P.

includes taxes & fees

8 Nov - 9 Nov

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

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

Killington

Ron L.

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

15. 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

8 Nov - 9 Nov

A modern kitchen with white cabinets, stainless steel appliances, a window with a view, and a 'GATHER' sign above the window.

16. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Rutland

includes taxes & fees

8 Nov - 9 Nov

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

17. Bearmont- Pool, HotTub, Fireplace

The Woods

Tyler B.

A two-story house with a covered porch and a gabled roof.

18. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Fair Haven

Molly T.

includes taxes & fees

8 Nov - 9 Nov

A rustic cabin surrounded by autumn foliage.

19. Beautiful home located in the Mad River Valley

Warren

Sloan S.

includes taxes & fees

11 Nov - 12 Nov

A room with a large window overlooking a forest in autumn.

20. Beautiful home located in the Mad River Valley

Warren

Lyra F.

includes taxes & fees

9 Nov - 10 Nov

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Learn more about Chittenden

Nestled in Vermont's Green Mountains, Chittenden offers pristine hiking trails around Chittenden Reservoir and the chance to spot wildlife. Rent a kayak to explore the reservoir's calm waters or visit nearby Killington for mountain biking adventures in summer.

See all hotels in Chittenden

A calm lake reflecting colorful autumn trees and a clear blue sky.

Top reviews in Chittenden

Snowed Inn

Killington

10/10 Excellent

Just like a hallmark card. The most friendliest and helpful staff you can find. We loved relaxing here and taking in the atmosphere. Lots of amazing restaurants within walking distance and the free shuttle was really helpful in getting around. So many small touches that made this place one of our favourite places to stay. AMAZING! We came in summer and hope to comeback one day in the winter and experience the snow and ski fields.