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Featured Holiday Homes in Randolph

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

2 out of 5
Chelsea
Located in Chelsea, this vacation home is within a 5-minute drive of Alden Speare Memorial Library and Chelsea Public Library.
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Dog-friendly home with panoramic mountain views, grill, deck, & pool table

Dog-friendly home with panoramic mountain views, grill, deck, & pool table

Middlesex
Located in Montpelier, this vacation home is in a rural location, within a 10-minute drive of Pavilion Building and Ceres.
Dog-friendly home with panoramic mountain views, grill, deck, & pool table
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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Spacious country home, beautiful sunsets, 40 acres

Spacious country home, beautiful sunsets, 40 acres

Tunbridge
This vacation home is 4.7 mi (7.5 km) from East Hill and 5.1 mi (8.1 km) from Tunbridge Public Library.
Spacious country home, beautiful sunsets, 40 acres
Rural Vermont with internet and Smart TV, cell phone works,  Dogs welcome.

Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome.

Washington
With a stay at this vacation home in Washington, you'll be on a river, and 5 mi (8.1 km) from Alden Speare Memorial Library and 5.6 mi (9 km) from Chelsea Public ...
Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome.
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2 out of 5
Barnard
Located in Barnard, this vacation home is on the waterfront, within a 10-minute drive of Amity Pond Natural Area and Saskadena Six Ski Area.
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
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!
Charming and spacious 5BR located in the heart of Waitsfield. Close to amenities

Charming and spacious 5BR located in the heart of Waitsfield. Close to amenities

2 out of 5
Waitsfield
With a stay at this vacation home in Waitsfield, you'll be within a 15-minute drive of Sugarbush Ski Resort and Mad River Valley.
Charming and spacious 5BR located in the heart of Waitsfield. Close to amenities
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
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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.

Randolph 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 Randolph vacation homes are the perfect way for you to wing it.

Holiday houses in Randolph 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 Randolph 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 Randolph adventures, obvs.

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

Randolph Holiday Homes essential information

Accommodation
679 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you, Dog-friendly home with panoramic mountain views, grill, deck, & pool table, The Old Orchard Home surrounded by a small apple orchard, large meadows, and a private pond, Spacious country home, beautiful sunsets, 40 acres, Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome., Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak, 5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!, Charming and spacious 5BR located in the heart of Waitsfield. Close to amenities, Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Top trending hotels in Randolph

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
A stay at Woodstock Inn & Resort places you in the heart of Woodstock, a 1-minute drive from Billings Farm and Museum and 7 minutes from Saskadena Six Ski ...
Woodstock Inn & Resort
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
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
Located in Woodstock, The Shire Woodstock is on a river, within a 5-minute walk of Mt Ascutney Hospital and Health Center Primary Care - Woodstock and Ottauquechee ...
The Shire Woodstock
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Comfort Inn & Suites Montpelier-Berlin

Comfort Inn & Suites Montpelier-Berlin

2.5 out of 5
213 Paine Turnpike N, Berlin, Montpelier, VT
Fully refundableReserve now, pay when you stay
When you stay at Comfort Inn & Suites Montpelier-Berlin in Montpelier, you'll be in a shopping district, within a 5-minute drive of Central Vermont Medical Center ...
Comfort Inn & Suites Montpelier-Berlin
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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.