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Featured Holiday Homes in Roxbury

Large, Comfortable, Retro 1970s Hillside Chalet

Large, Comfortable, Retro 1970s Hillside Chalet

Waterbury
Located in Waterbury, this vacation home is a 1-minute drive from Mad River Valley and 6 minutes from Ben and Jerry's Factory.
Large, Comfortable, Retro 1970s Hillside Chalet
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

Killington
With a stay at this vacation home in Killington (North Sherburne), you'll be within a 15-minute drive of Pico Mountain at Killington Ski Resort and Killington ...
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
Beautiful 4-Bedroom Home beside Middlebury College

Beautiful 4-Bedroom Home beside Middlebury College

Middlebury
With a stay at this vacation home in Middlebury, you'll be a 1-minute walk from Middlebury College and 6 minutes by foot from Kevin P. Mahaney '84 Center for ...
Beautiful 4-Bedroom Home beside Middlebury College
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Killington Vermont Ski and Snowmobiling House

Killington Vermont Ski and Snowmobiling House

Pittsfield
Located in Pittsfield, this vacation home is within a 15-minute drive of Pico Mountain at Killington Ski Resort and Killington Resort.
Killington Vermont Ski and Snowmobiling House
The Brandon Inn - King Room

The Brandon Inn - King Room

Brandon
The price is AU$360 per night from 23 Dec to 24 Dec
AU$360
includes taxes & fees
23 Dec - 24 Dec
A stay at this vacation home places you in the heart of Brandon, within a 10-minute walk of Judith Reilly Gallery and Stephen A Douglas Birthplace.
The Brandon Inn - King Room
Mountain Top - Fresh Pond - Killington - Hot Tub

Mountain Top - Fresh Pond - Killington - Hot Tub

Pittsfield
Located in Pittsfield, this vacation home is on a lake, within a 15-minute drive of Green Mountain National Forest and Gifford Woods State Park.
Mountain Top - Fresh Pond - Killington - Hot Tub
A peaceful luxurious retreat with stunning mountain views & nearby skiing!

A peaceful luxurious retreat with stunning mountain views & nearby skiing!

Moretown
When you stay at this vacation home in Moretown, you'll be in the mountains and steps from Mad River Valley.
A peaceful luxurious retreat with stunning mountain views & nearby skiing!
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

chittenden
When you stay at this vacation home in Chittenden, you'll be in the mountains and steps from Green Mountain National Forest.
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill
Secluded Vermont Home with Stunning Private View! Prime Location!

Secluded Vermont Home with Stunning Private View! Prime Location!

waitsfield
With a stay at this vacation home in Waitsfield, you'll be in the mountains, just steps from Mad River Valley and a 2-minute drive from Green Mountain Cultural ...
Secluded Vermont Home with Stunning Private View! Prime Location!
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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.

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

Holiday houses in Roxbury 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 Roxbury 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 Roxbury adventures, obvs.

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

Roxbury Holiday Homes essential information

Accommodation
220 Holiday Homes
Lowest Price
AU$241
Highest Price
AU$360
Popular accommodation
Large, Comfortable, Retro 1970s Hillside Chalet, Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail, Beautiful 4-Bedroom Home beside Middlebury College, Killington Vermont Ski and Snowmobiling House, The Brandon Inn - King Room, Mountain Top - Fresh Pond - Killington - Hot Tub, A peaceful luxurious retreat with stunning mountain views & nearby skiing!, 6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill, Secluded Vermont Home with Stunning Private View! Prime Location!

Top trending hotels in Roxbury

Rustic Roxbury Ski Farmhouse with Trails!

Rustic Roxbury Ski Farmhouse with Trails!

Roxbury
With a stay at this vacation home in Roxbury, you'll be within a 15-minute drive of Chandler Music Hall and Playhouse Movie Theatre.
Rustic Roxbury Ski Farmhouse with Trails!
Best Western Plus Waterbury - Stowe

Best Western Plus Waterbury - Stowe

3 out of 5
45 Blush Hill Rd, Waterbury, VT
Fully refundableReserve now, pay when you stay
The price is AU$265 per night from 5 Jan to 6 Jan
AU$265
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Waterbury, Best Western Plus Waterbury - Stowe is in the mountains, within a 5-minute drive of Ben and Jerry's Factory and The Cabot Annex Store.
Best Western Plus Waterbury - Stowe
Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is AU$241 per night from 1 Jan to 2 Jan
AU$241
includes taxes & fees
1 Jan - 2 Jan 2025
A stay at Middlebury Inn places you in the heart of Middlebury, steps from Town Hall Theater and 3 minutes by foot from National Museum of the Morgan Horse.
Middlebury Inn
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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
The price is AU$265 per night from 29 Dec to 30 Dec
AU$265
includes taxes & fees
29 Dec - 30 Dec
Located in Montpelier, Comfort Inn & Suites Montpelier-Berlin is in a shopping district, a 2-minute drive from Central Vermont Medical Center and 5 minutes from ...
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.