Book Holiday Homes in Guilford

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Featured Holiday Homes in Guilford

Waterfront House with picture-perfect views from all 3 levels.

Waterfront House with picture-perfect views from all 3 levels.

Westbrook
Located in Westbrook (Westbrook Center), this vacation home is within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.
Waterfront House with picture-perfect views from all 3 levels.
Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton
With a stay at this vacation home in Clinton, you'll be near the beach, just a 4-minute walk from Adam Stanton House and General Store Museum and 12 minutes ...
Large Charming Historic House close to Beaches
Cozy Westbrook Vacation Rental - Walk to Beach!

Cozy Westbrook Vacation Rental - Walk to Beach!

Westbrook
With a stay at this vacation home in Westbrook (Westbrook Center), you'll be a 1-minute drive from Westbrook Town Beach and 6 minutes from Tanger Outlets.
Cozy Westbrook Vacation Rental - Walk to Beach!
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New Madison beach house - Ocean front- Great views- booking Summer 2025

New Madison beach house - Ocean front- Great views- booking Summer 2025

Madison
Located in Madison, this vacation home is by the ocean, within a 10-minute drive of Deacon John Grave House and Anna Mia's.
New Madison beach house - Ocean front- Great views- booking Summer 2025
Waterfront Beach House

Waterfront Beach House

Clinton
Located in Clinton, this vacation home is by the ocean, within a 5-minute drive of Clinton Plaza Shopping Center and Adam Stanton House and General Store ...
Waterfront Beach House
Luxe Lake House in Connecticut

Luxe Lake House in Connecticut

Haddam
The price is AU$1,832 per night from 15 Apr to 16 Apr
AU$1,832
includes taxes & fees
15 Apr - 16 Apr
Located in Higganum, this vacation home is on the waterfront, a 2-minute drive from Millers Pond State Park and 7 minutes from Ron McCutcheon Park.
Luxe Lake House in Connecticut
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Clinton
When you stay at this vacation home in Clinton, you'll be near the beach and 11 minutes by foot from Clinton Town Beach.
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge

Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge

Westbrook
With a stay at this vacation home in Westbrook (Westbrook Center), you'll be a 5-minute drive from Westbrook Town Beach and 5 minutes from Tanger Outlets.
Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge
Magic Place

Magic Place

Southold
The price is AU$1,470 per night from 14 Apr to 15 Apr
AU$1,470
includes taxes & fees
14 Apr - 15 Apr
With a stay at this vacation home in Southold, you'll be within a 5-minute drive of Sparkling Pointe and Horton Point Park.
Magic Place
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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
594 Holiday Homes
Lowest Price
AU$155
Highest Price
AU$1,832
Popular accommodation
Waterfront House with picture-perfect views from all 3 levels., Large Charming Historic House close to Beaches, Cozy Westbrook Vacation Rental - Walk to Beach!, New Madison beach house - Ocean front- Great views- booking Summer 2025, Waterfront Beach House, Luxe Lake House in Connecticut, Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included, Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge, Magic Place

Top trending hotels in Guilford

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 20 Apr to 21 Apr
AU$216
includes taxes & fees
20 Apr - 21 Apr
New Haven Hotel is centrally located in New Haven, a 4-minute walk from Shubert Theater and 5 minutes by foot from New Haven Green.
New Haven Hotel
Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
The price is AU$155 per night from 6 Apr to 7 Apr
AU$155
includes taxes & fees
6 Apr - 7 Apr
With a stay at Clarion Inn in North Haven, you'll be within a 15-minute drive of Yale University and Quinnipiac University.
Clarion Inn
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is AU$263 per night from 28 Apr to 29 Apr
AU$263
includes taxes & fees
28 Apr - 29 Apr
With a stay at Omni New Haven Hotel at Yale, you'll be centrally located in New Haven, steps from New Haven Green and within a 5-minute walk of Yale University ...
Omni New Haven Hotel at Yale
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Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$392 per night from 6 Apr to 7 Apr
AU$392
includes taxes & fees
6 Apr - 7 Apr
With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing ...
Water's Edge Resort & Spa
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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.