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Featured Holiday Homes in Castleton

Lakefront home near ski resorts with water view, dock, deck, fireplaces, & W/D

Lakefront home near ski resorts with water view, dock, deck, fireplaces, & W/D

Castleton
With a stay at this vacation home in Bomoseen, you'll be on the waterfront, just steps from Lake Bomoseen and a 4-minute drive from Halfmoon Pond State ...
Lakefront home near ski resorts with water view, dock, deck, fireplaces, & W/D
3-bedroom townhome in tranquil Ticonderoga with AC, WiFi close to Lake George!

3-bedroom townhome in tranquil Ticonderoga with AC, WiFi close to Lake George!

Ticonderoga
Located in Ticonderoga, this vacation home is within a 15-minute drive of Lake George and Fort Ticonderoga.
3-bedroom townhome in tranquil Ticonderoga with AC, WiFi close to Lake George!
The Old Orchard Home surrounded by a small apple orchard, large meadows, and a private pond

The Old Orchard Home surrounded by a small apple orchard, large meadows, and a private pond

Brandon
Located in Brandon, this vacation home is in a rural location, within a 5-minute drive of Brandon Museum and Judith Reilly Gallery.
The Old Orchard Home surrounded by a small apple orchard, large meadows, and a private pond
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Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC

Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC

Castleton
When you stay at this vacation home in Bomoseen, you'll be on the waterfront, within a 5-minute drive of Prospect Bay Country Club and Lake Bomoseen.
Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

killington
With a stay at this vacation home in Killington, you'll be steps from Killington Resort and a 2-minute drive from Black Dog Sports.
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Killington
With a stay at this vacation home in Killington, you'll be steps from Green Mountain National Forest and a 3-minute drive from Pico Mountain at Killington Ski ...
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
NEW LISTING! Cozy Trotter (4-Bedroom Home) - Pets Allowed

NEW LISTING! Cozy Trotter (4-Bedroom Home) - Pets Allowed

2 out of 5
96 Champlain Avenue, Ticonderoga, NY
With a stay at this vacation home in Ticonderoga, you'll be a 2-minute drive from Lake George and 9 minutes from Fort Ticonderoga.
NEW LISTING! Cozy Trotter (4-Bedroom Home) - Pets Allowed
Cottage on east side of Lake Bomoseen, on-site boat slip included

Cottage on east side of Lake Bomoseen, on-site boat slip included

Bomoseen
With a stay at this vacation home in Bomoseen, you'll be on a lake, just steps from Lake Bomoseen and a 3-minute drive from Prospect Bay Country Club.
Cottage on east side of Lake Bomoseen, on-site boat slip included
Charming dog-friendly home with private deck, firepit, washer/dryer, & cable

Charming dog-friendly home with private deck, firepit, washer/dryer, & cable

Wallingford
With a stay at this vacation home in East Wallingford, you'll be within a 5-minute drive of Green Mountain National Forest and Shrewsbury Free Library.
Charming dog-friendly home with private deck, firepit, washer/dryer, & cable
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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.

Castleton Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Castleton vacation homes are the perfect way for you to wing it.

Holiday houses in Castleton let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Castleton in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Castleton adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Castleton with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Castleton vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Castleton Holiday Homes essential information

Accommodation
613 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Lakefront home near ski resorts with water view, dock, deck, fireplaces, & W/D, 3-bedroom townhome in tranquil Ticonderoga with AC, WiFi close to Lake George!, The Old Orchard Home surrounded by a small apple orchard, large meadows, and a private pond, Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC, 5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!, Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski, NEW LISTING! Cozy Trotter (4-Bedroom Home) - Pets Allowed, Cottage on east side of Lake Bomoseen, on-site boat slip included, Charming dog-friendly home with private deck, firepit, washer/dryer, & cable

Top trending hotels in Castleton

Pastoral, dog-friendly home surrounded by lush woodland with free WiFi & firepit

Pastoral, dog-friendly home surrounded by lush woodland with free WiFi & firepit

Castleton
Located in Castleton, this vacation home is on the waterfront, a 1-minute drive from Lake Bomoseen and 7 minutes from Marsh Pond Wildlife Management Area.
Pastoral, dog-friendly home surrounded by lush woodland with free WiFi & firepit
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
With a stay at Comfort Inn Rutland - Killington in Rutland, you'll be 0.6 mi (1 km) from Rutland Regional Medical Center and 9.8 mi (15.7 km) from Pico Mountain ...
Comfort Inn Rutland - Killington
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
With a stay at Killington Mountain Lodge, Tapestry Collection by Hilton in Killington, you'll be next to a golf course, just steps from Killington Resort and ...
Killington Mountain Lodge, Tapestry Collection by Hilton
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North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr, Killington, VT
Fully refundableReserve now, pay when you stay
Located in Killington, North Star Lodge and Resort is in the mountains, a 3-minute drive from Killington Resort and 5 minutes from Killington Golf Course.
North Star Lodge and Resort
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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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^Subject to availability and chosen travel dates.