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
Book a stay at this beach vacation home in Westbrook. Enjoy free WiFi, a beach locale, and furnished patios. Popular attractions Westbrook Town Beach and Tanger ...
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
Stay at this vacation home in Clinton. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Adam Stanton House and General Store Museum and ...
Large Charming Historic House close to Beaches
Cozy Westbrook Vacation Rental - Walk to Beach!

Cozy Westbrook Vacation Rental - Walk to Beach!

Westbrook
Stay at this vacation home in Westbrook. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Westbrook Town Beach and Tanger ...
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
Book a stay at this beach vacation home in Madison. Enjoy free WiFi, a beach locale, and patios. Popular attractions Chaffinch Island State Park and Henry Whitfield ...
New Madison beach house - Ocean front- Great views- booking Summer 2025
Waterfront Beach House

Waterfront Beach House

Clinton
Stay at this vacation home in Clinton. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Clinton Plaza Shopping Center and Clinton Town ...
Waterfront Beach House
Luxe Lake House in Connecticut

Luxe Lake House in Connecticut

Haddam
Stay at this vacation home in Higganum. Enjoy free WiFi, a garden, and patios. Popular attractions Millers Pond State Park and Ron McCutcheon Park are located ...
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
Stay at this vacation home in Clinton. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Clinton Town Beach and Clinton Plaza Shopping ...
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
Stay at this vacation home in Westbrook. Enjoy free WiFi, a garden, and patios. Popular attractions Chalker Beach and Tanger Outlets are located nearby.
Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge
Magic Place

Magic Place

Southold
Stay at this vacation home in Southold. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Sparkling Pointe and The Old Field Vineyards are ...
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
575 Holiday Homes
Lowest Price
NZ$170
Highest Price
NZ$431
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
The price is NZ$238 per night from 20 Apr to 21 Apr
NZ$238
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
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 NZ$170 per night from 6 Apr to 7 Apr
NZ$170
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Clarion Inn
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 NZ$431 per night from 14 Apr to 15 Apr
NZ$431
includes taxes & fees
14 Apr - 15 Apr
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
Water's Edge Resort & Spa
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Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane, Milford, CT
Fully refundableReserve now, pay when you stay
The price is NZ$240 per night from 14 Apr to 15 Apr
NZ$240
includes taxes & fees
14 Apr - 15 Apr
Stay at this 3-star business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hyatt Place Milford / New Haven
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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.