Book Holiday Homes in Guilford

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Guilford

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Dover
When you stay at this vacation home in West Dover, you'll be in the mountains, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Newfane
Located in Newfane, this vacation home is a 3-minute drive from Rock River Preserve and 6 minutes from West River.
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
1810 Brook Side Mill/House / EV Level 2 Charging on Site

1810 Brook Side Mill/House / EV Level 2 Charging on Site

Shelburne Falls
Located in Shelburne Falls, this vacation home is in a rural location, within a 5-minute drive of Deerfield River and Bald Mountain Pottery.
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Save an average of 15% on thousands of hotels when you're signed in
Relaxing Retreat in the Heart of Dover

Relaxing Retreat in the Heart of Dover

Dover
Located in West Dover, this vacation home is in a rural location, within a 15-minute walk of Green Mountain National Forest and North Branch Deerfield ...
Relaxing Retreat in the Heart of Dover
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

Wardsboro
Located in Wardsboro, this vacation home is in the mountains, within a 15-minute drive of Green Mountain National Forest and Wardsboro Public Library.
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Dover
The price is AU$556 per night from 24 Mar to 25 Mar
AU$556
per night
24 Mar - 25 Mar
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!
Bright three-level home with water views, jetted tub, firepit, and pool table

Bright three-level home with water views, jetted tub, firepit, and pool table

Jacksonville
Located in Jacksonville, this vacation home is on a lake, a 1-minute drive from Jacksonville Pond and 7 minutes from Honora Winery.
Bright three-level home with water views, jetted tub, firepit, and pool table
Cozy retreat near slopes

Cozy retreat near slopes

Dover
With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Cozy retreat near slopes
Wilmington Vacation Rental Near Hiking and Skiing!

Wilmington Vacation Rental Near Hiking and Skiing!

Wilmington
Located in Wilmington, this vacation home is a 1-minute drive from Green Mountain National Forest and 7 minutes from North Branch Deerfield River.
Wilmington Vacation Rental Near Hiking and Skiing!
Don't see what you're looking for?
See all available properties in Guilford
View all properties
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.

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

Holiday houses in Guilford 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 Guilford 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 Guilford adventures, obvs.

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

Guilford Holiday Homes essential information

Accommodation
367 Holiday Homes
Lowest Price
AU$190
Highest Price
AU$556
Popular accommodation
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck, 1810 Brook Side Mill/House / EV Level 2 Charging on Site, Relaxing Retreat in the Heart of Dover, Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!, Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!, Bright three-level home with water views, jetted tub, firepit, and pool table, Cozy retreat near slopes, Wilmington Vacation Rental Near Hiking and Skiing!

Top trending hotels in Guilford

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Stony Hill Rd South, Guilford, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$456 per night from 25 Mar to 26 Mar
AU$456
includes taxes & fees
25 Mar - 26 Mar
With a stay at Vikings Villages Resort in Brattleboro, you'll be 6.1 mi (9.8 km) from Vermont Marketplace and 7.5 mi (12.1 km) from The Stone Church.
Vikings Villages Resort
The Jelly Mill-A River Retreat

The Jelly Mill-A River Retreat

Guilford
When you stay at this vacation home in Brattleboro, you'll be on the waterfront and 7 minutes by car from Green River Wildlife Management Area.
The Jelly Mill-A River Retreat
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 16 Mar to 17 Mar
AU$190
includes taxes & fees
16 Mar - 17 Mar
A stay at Colonial Motel And Spa places you in the heart of Brattleboro, steps from Brattleboro Bowl and 11 minutes by foot from New England Center for Circus ...
Colonial Motel And Spa
Save an average of 15% on thousands of hotels when you're signed in
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 23 Mar to 24 Mar
AU$191
includes taxes & fees
23 Mar - 24 Mar
When you stay at Comfort Inn & Suites Brattleboro I-91 in Brattleboro, you'll be near ski lifts, within a 10-minute walk of Connecticut River and United States ...
Comfort Inn & Suites Brattleboro I-91
Don't see what you're looking for?
See all available properties in Guilford
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.