Chittenden Holiday Rentals

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Check prices for these dates

Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Chittenden holiday rentals

Exterior
Robert Frost Mountain Cabins

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (40)
"Ammazing,would go again!"
United States
Joseph
The price is HK$1,867
HK$2,036 total
includes taxes & fees
11 Jan - 12 Jan 2026
Robert Frost Mountain Cabins
Exterior
Secluded retreat in the trees

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (37)
"Absolutely beautiful! So pleased with everything about our stay!"
United States
Gwen B.
The price is HK$980
HK$1,830 total
includes taxes & fees
19 Dec - 20 Dec
Secluded retreat in the trees
Exterior detail
Ben & Jerry’s Studio | 10 Min to Killington

Ben & Jerry’s Studio | 10 Min to Killington

Ben & Jerry’s Studio | 10 Min to Killington
Bridgewater
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is HK$887
HK$1,829 total
includes taxes & fees
14 Jan - 15 Jan 2026
Ben & Jerry’s Studio | 10 Min to Killington
Property grounds
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.2 out of 10, Good, (44)
"Quick trip to and from Killington mt"
United States
Phillip F.
The price is HK$669
HK$2,275 total
includes taxes & fees
21 Dec - 22 Dec
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Interior
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Killington
9.6 out of 10, Exceptional, (4)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is HK$1,249
HK$2,801 total
includes taxes & fees
22 Dec - 23 Dec
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Exterior
*Downtown Middlebury Waterfall Studio Apartment*

*Downtown Middlebury Waterfall Studio Apartment*

*Downtown Middlebury Waterfall Studio Apartment*
Middlebury
10.0 out of 10, Exceptional, (7)
"fantastic!"
United States
Diana L.
The price is HK$653
HK$2,266 total
includes taxes & fees
8 Jan - 9 Jan 2026
*Downtown Middlebury Waterfall Studio Apartment*
Exterior
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
2.0 star property
Killington
10.0 out of 10, Exceptional, (11)
"The cabin was cozy. It was set up nicely and had all the necessities we needed."
United States
Philip
The price is HK$2,721
HK$5,875 total
includes taxes & fees
19 Dec - 20 Dec
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Indoor pool, a heated pool
Modern Mountain Condo with Spa

Modern Mountain Condo with Spa

Modern Mountain Condo with Spa
The Woods
9.8 out of 10, Exceptional, (8)
"The property met our expectations. Great property for parties less than 6 people."
United States
Michael H.
The price is HK$1,484
HK$3,392 total
includes taxes & fees
21 Dec - 22 Dec
Modern Mountain Condo with Spa
Indoor pool
Cozy condo on ski shuttle route with free WiFi & full ktichen

Cozy condo on ski shuttle route with free WiFi & full ktichen

Cozy condo on ski shuttle route with free WiFi & full ktichen
Killington
8.4 out of 10, Very good, (38)
"Great place. Met our needs. "
United States
Sean K.
The price is HK$918
HK$2,645 total
includes taxes & fees
11 Jan - 12 Jan 2026
Cozy condo on ski shuttle route with free WiFi & full ktichen
Beach
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is HK$2,528
HK$5,725 total
includes taxes & fees
5 Jan - 6 Jan 2026
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Fridge, microwave, oven, stovetop
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (67)
"Very pleasant stay, at a unique and interesting property."
United States
Steve P.
The price is HK$856
HK$1,394 total
includes taxes & fees
21 Dec - 22 Dec
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Indoor pool
Mountain Green

Mountain Green

Mountain Green
2.0 star property
Killington
7.0 out of 10, Good, (15)
"Great communication from Jeff."
United States
Dennis
The price is HK$1,653
HK$2,218 total
includes taxes & fees
21 Dec - 22 Dec
Mountain Green
Terrace/patio
Killington condo 5 min to killington resort

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (8)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
The price is HK$1,439
HK$3,323 total
includes taxes & fees
4 Jan - 5 Jan 2026
Killington condo 5 min to killington resort
1 bedroom, iron/ironing board, travel cot, free WiFi
Cozy Cabin Retreat

Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (33)
"A wonderful cabin. I need to come back sometime."
United States
Fletcher F.
The price is HK$917
HK$1,655 total
includes taxes & fees
23 Dec - 24 Dec
Cozy Cabin Retreat
Exterior
Doc's Lake house 1st floor, 2 bedroom apartment

Doc's Lake house 1st floor, 2 bedroom apartment

Doc's Lake house 1st floor, 2 bedroom apartment
Salisbury
10.0 out of 10, Exceptional, (72)
"Very clean and comfortable rental. "
United States
John S.
The price is HK$1,050
HK$1,577 total
includes taxes & fees
19 Dec - 20 Dec
Doc's Lake house 1st floor, 2 bedroom apartment
Fridge, microwave, oven, stovetop
The Bomoseen Bungalow: Vermont Lake House with Private Dock

The Bomoseen Bungalow: Vermont Lake House with Private Dock

The Bomoseen Bungalow: Vermont Lake House with Private Dock
2.0 star property
Bomoseen
9.6 out of 10, Exceptional, (4)
"Nice place to stay. Very well equipped and clean."
United States
Rich S.
The price is HK$1,378
HK$4,348 total
includes taxes & fees
22 Dec - 23 Dec
The Bomoseen Bungalow: Vermont Lake House with Private Dock
Property grounds
Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.8 out of 10, Exceptional, (39)
"We had a great time staying at this house during our Sugarbush skiing trip this February. The place is easy to access and is close to the ski resort. The house had everything we needed for a comfortable stay. I highly recommend this rental."
United States
Dmitriy K.
Beautiful home located in the Mad River Valley
Property grounds
Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.6 out of 10, Excellent, (45)
"Very close to Killington and in the shuttle route."
United States
Craig C.
The price is HK$1,533
HK$4,162 total
includes taxes & fees
8 Jan - 9 Jan 2026
Resort condo with mountain views, full kitchen, and free WiFi
Property grounds
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (3)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is HK$1,011
HK$2,231 total
includes taxes & fees
15 Jan - 16 Jan 2026
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Interior
Make memories at this unique and family-friendly Vermont cabin!

Make memories at this unique and family-friendly Vermont cabin!

Make memories at this unique and family-friendly Vermont cabin!
Fair Haven
10.0 out of 10, Exceptional, (10)
"Loved the place! Just an hour from lake george! "
United States
Yami N.
The price is HK$1,393
HK$2,284 total
includes taxes & fees
19 Dec - 20 Dec
Make memories at this unique and family-friendly Vermont cabin!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chittenden Hotel Reviews

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Luxurious and friendly resort! Loved it"
Elizabeth 1-night trip
Posted 5 hours ago
Woodstock Inn & Resort

Find out more about Chittenden

Search for holiday rentals in Chittenden on Expedia! You can easily find your home rentals, villas, holiday apartments in Chittenden using one of the methods below:

  • View our selection of featured holiday rentals in Chittenden
  • Use the map to find apartments and other holiday homes in the Chittenden neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chittenden while they last

Look no further and take a look at our great range of rental properties in Chittenden!

Frequently asked questions

Are there holiday rentals in Chittenden?

Yes, there are holiday rentals close to the most popular sights in Chittenden, or you can select a more secluded option if you're looking for a relaxing stay. Chittenden is known for its ski areas and mountain views. Make sure you have time to check out the lake views and bars during your trip.

What are some of the best holiday rentals that Chittenden has to offer?

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!: This holiday home rental outside of Chittenden is located near skiing, and has a patio, a selection of games and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Chittenden?

Choose from 10 Expedia holiday rentals in Chittenden for a memorable holiday.

What can I see and do in Chittenden?

Green Mountain National Forest and Lefferts Pond are a couple of lovely local spots to get outside and enjoy nature. Killington Resort and New England Maple Museum are a couple of places you'll find in the wider area.

What are holiday rentals like in Chittenden?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chittenden. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for families.