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Our top choices for Castleton holiday rentals

1. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
Fair Haven
9.2 out of 10, Wonderful, (39 reviews)
"Great quick stay on the way to the Adirondacks"
United States
Natalie B.
The price is £215
includes taxes & fees
16 Nov - 17 Nov
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

2. Off-Grid Mongolian Yurt on Vermont Sheep Farm

Off-Grid Mongolian Yurt on Vermont Sheep Farm
Poultney
The price is £126
includes taxes & fees
16 Nov - 17 Nov
Off-Grid Mongolian Yurt on Vermont Sheep Farm

3. Unique family-friendly Vermont cabin!

Unique family-friendly Vermont cabin!
Fair Haven
10.0 out of 10, Exceptional, (34 reviews)
"Another great stay."
United States
leonard
The price is £224
includes taxes & fees
16 Nov - 17 Nov
Unique family-friendly Vermont cabin!

4. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (18 reviews)
"WE ENJOYED OUR STAY"
United States
Susan E.
The price is £126
includes taxes & fees
22 Nov - 23 Nov
Cozy Rutland Retreat

5. Rutland apartment on the bus route with central A/C, near Pico

Rutland apartment on the bus route with central A/C, near Pico
Rutland
8.0 out of 10, Very good, (1 review)
"Spotless interior, but the exterior will benifit from a refresh.Conveniently walkable for shops and restaurants."
United States
Thomas A.
The price is £263
includes taxes & fees
16 Nov - 17 Nov
Rutland apartment on the bus route with central A/C, near Pico

6. Comfy Cottage with Private Hot Tub in Historic East Poultney

Comfy Cottage with Private Hot Tub in Historic East Poultney
Poultney
10.0 out of 10, Exceptional, (18 reviews)
"Very comfortable and clean cottage in a beautiful village. The shower in the bath is incredible. "
United States
Karen C.
The price is £291
includes taxes & fees
16 Nov - 17 Nov
Comfy Cottage with Private Hot Tub in Historic East Poultney

7. Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (31 reviews)
"It was a great place, clean rooms, nice environment, cabins, family friendly, right on lake"
United States
Matthew
The price is £131
includes taxes & fees
16 Nov - 17 Nov
Trout House Village Resort

8. Kingsley Homestead - 2 Bedroom retreat

Kingsley Homestead - 2 Bedroom retreat
Rutland
The price is £145
includes taxes & fees
18 Nov - 19 Nov
Kingsley Homestead - 2 Bedroom retreat

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

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.4 out of 10, Exceptional, (8 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is £212
includes taxes & fees
16 Nov - 17 Nov
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

10. Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
Chittenden
9.4 out of 10, Exceptional, (6 reviews)
"Loved this stay - the farmhouse is authentic and oozes charm! Everything about this stay was easy - 20min drive to the slopes, 15 min to downtown Rutland, and an extremely well-equipped house to easily accommodate the six of us. Superb communication from the host both prior to and during our stay (promptly answered several questions for us). If you want a vintage farmhouse feel as opposed to a modern condo-style stay, this is the place for you!"
United States
Carl P.
The price is £469
includes taxes & fees
16 Nov - 17 Nov
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

11. Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you

Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you
Chittenden
The price is £270
includes taxes & fees
16 Nov - 17 Nov
Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you

12. 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, (97 reviews)
"The cottage was just lovely. Very comfortable. And the host was really nice and helpful. A wonderful stay!"
United States
Laura Ann
The price is £148
includes taxes & fees
16 Nov - 17 Nov
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

13. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
The price is £291
includes taxes & fees
16 Nov - 17 Nov
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

14. The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.6 out of 10, Exceptional, (24 reviews)
"The communication with Host was awesome to a question we had; Dave's response was so helpful. Beautiful place, quiet. Get ‘get-away’."
United States
Diane
The price is £383
includes taxes & fees
16 Nov - 17 Nov
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

15. Peaceful 1-bedroom bungalow with AC in charming Wells

Peaceful 1-bedroom bungalow with AC in charming Wells
Wells
9.6 out of 10, Exceptional, (4 reviews)
"This is the most amazing spot. Our second time staying here after the horse races and we will definitely be back next summer. You guys are awesome!"
United States
Donna A.
The price is £191
includes taxes & fees
30 Nov - 1 Dec
Peaceful 1-bedroom bungalow with AC in charming Wells

16. 4BR Home | Walk Downtown Rutland + Trails

4BR Home | Walk Downtown Rutland + Trails
Rutland
10.0 out of 10, Exceptional, (8 reviews)
"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "
United States
Dominic C.
The price is £265
includes taxes & fees
16 Nov - 17 Nov
4BR Home | Walk Downtown Rutland + Trails

17. Jack S`Bearo - Slopes, Fireplace, Pool

Jack S`Bearo - Slopes, Fireplace, Pool
Killington
10.0 out of 10, Exceptional, (17 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
United States
Joseph S.
The price is £204
includes taxes & fees
16 Nov - 17 Nov
Jack S`Bearo - Slopes, Fireplace, Pool

18. Glamping hut with WiFi in Ripton, biking, hiking, skiing

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
9.4 out of 10, Exceptional, (10 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
The price is £167
includes taxes & fees
17 Nov - 18 Nov
Glamping hut with WiFi in Ripton, biking, hiking, skiing

19. Mountain Green ground-floor condo with private yard off the patio

Mountain Green ground-floor condo with private yard off the patio
Killington
The price is £223
includes taxes & fees
18 Nov - 19 Nov
Mountain Green ground-floor condo with private yard off the patio

20. Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.

Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
Rutland
9.4 out of 10, Exceptional, (6 reviews)
"Perfect spot for a large group to enjoy Rutland, Killington, and the surrounding area. Plenty of beds for everyone, and bathrooms so no one felt cramped whatsoever. Beautiful home and safe neighborhood. All around a great stay. If we come back for the US Open of MTB next year, this house would be high on our list to stay in again."
United States
Matthew T.
The price is £744
includes taxes & fees
16 Nov - 17 Nov
Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
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.

Find holiday rentals that suit your style

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Find out more about Castleton

Everything you need to know about Castleton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Castleton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castleton holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castleton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castleton. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castleton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castleton holiday rentals we have selected for you start as low as £125 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Castleton rentals

At Expedia, we put the best Castleton holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castleton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castleton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castleton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Castleton?

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

How many holiday rentals will I find in Castleton?

Choose from 16 Expedia holiday rentals in Castleton for a memorable holiday.

What can I see and do in Castleton?

Lake Bomoseen and Zion Hill are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Taconic Mountains Ramble State Park and Sargent Hill Wilderness Preserve.

What are holiday rentals like in Castleton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Castleton. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.