Book Holiday Homes in Guilford
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Featured Holiday Homes in Guilford

The Jelly Mill-A Peaceful River Retreat

Private Family Estate for any Season

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Story Book Lake Front Chateau with Private Beach!

Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

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

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Lovely 2nd Floor Apartment
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 | 446 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | The Jelly Mill-A Peaceful River Retreat, Private Family Estate for any Season, Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort.., Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included, Story Book Lake Front Chateau with Private Beach!, Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!, Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!, Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort, Lovely 2nd Floor Apartment |
Top Locations for Holiday Homes in Guilford
More accommodations in Guilford
Top trending hotels in Guilford

Vikings Villages Resort

The Jelly Mill-A Peaceful River Retreat

Red Roof Inn PLUS+ South Deerfield – Amherst

Colonial Motel And Spa
More ways to explore Guilford
Top picks
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^Subject to availability and chosen travel dates.