Book Holiday Homes in Guilford

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Featured Holiday Homes in Guilford

FaLL Western Mass Getaway-Airhockey-Firepit

FaLL Western Mass Getaway-Airhockey-Firepit

Colrain MA
Located in Colrain, this vacation home is within a 5-minute drive of Arthur A. Smith Covered Bridge and G. William Pitt House and Collection.
Opens in a new windowFaLL Western Mass Getaway-Airhockey-Firepit
Amazing lake views & access,HotTub & sauna, quality game Rm.  190-5 star Reviews

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Wilmington VT
Located in Wilmington, this vacation home is on the waterfront, within a 5-minute walk of Deerfield River and Harriman Reservoir.
Opens in a new windowAmazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Dover VT
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.
Opens in a new window 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
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Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington VT
Located in Wilmington, this vacation home is on a lake, a 1-minute drive from Lake Raponda and 9 minutes from South Main Street.
Opens in a new windowBeautiful Custom Built Timber Frame Home, Sleeps 11
Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

West Dover Vermont VT
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.
Opens in a new windowLuxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!
Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont MA
The price is AU$613 per night from 11 Feb to 12 Feb
AU$613
11 Feb - 12 Feb
includes taxes & fees
With a stay at this vacation home in Charlemont, you'll be a 4-minute walk from Charlemont Federated Church and 5 minutes by foot from Charlemont Historical ...
Opens in a new windowRiverbend Berkshire East Basecamp - 3 bedrooms available
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2 out of 5
Shelburne Falls MA
With a stay at this vacation home in Shelburne Falls, you'll be a 1-minute walk from Deerfield River and 7 minutes by foot from Arms Cemetery.
Opens in a new windowStylish new 2 bedroom property in enchanting Shelburne Falls Village.
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Townshend VT
Located in Townshend, this vacation home is in the mountains, within a 15-minute drive of West River and Newfane Town Hall.
Opens in a new windowLuxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
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 VT
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.
Opens in a new windowBrand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
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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.

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
388 Holiday Homes
Lowest Price
AU$140
Highest Price
AU$613
Popular accommodation
FaLL Western Mass Getaway-Airhockey-Firepit, Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews, 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base, Beautiful Custom Built Timber Frame Home, Sleeps 11, Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!, Riverbend Berkshire East Basecamp - 3 bedrooms available, Stylish new 2 bedroom property in enchanting Shelburne Falls Village., Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Top trending hotels in Guilford

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
The price is AU$358 per night from 11 Mar to 12 Mar
AU$358
11 Mar - 12 Mar
includes taxes & fees
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.
Opens in a new windowVikings Villages Resort
Green River Bridge Inn

Green River Bridge Inn

3 out of 5
2435 Stage Rd Guilford VT
When you stay at Green River Bridge Inn in Brattleboro, you'll be 11 minutes by car from Green River Wildlife Management Area.
Opens in a new windowGreen River Bridge Inn
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd South Deerfield MA
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 1 Mar to 2 Mar
AU$140
1 Mar - 2 Mar
includes taxes & fees
With a stay at Red Roof Inn PLUS+ South Deerfield – Amherst in South Deerfield, you'll be within a 15-minute drive of University of Massachusetts Amherst and ...
Opens in a new windowRed Roof Inn PLUS+ South Deerfield – Amherst
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Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
The price is AU$537 per night from 4 Mar to 5 Mar
AU$537
4 Mar - 5 Mar
includes taxes & fees
Located in West Dover, Grand Summit Resort, A Vail Resorts Property is a 1-minute drive from Mount Snow and 7 minutes from Mount Snow Golf Course.
Opens in a new windowMount Snow Grand Summit 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.