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
The price is NZ$1,590 per night from 6 May to 7 May
NZ$1,590
includes taxes & fees
6 May - 7 May
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
The price is NZ$1,535 per night from 7 May to 8 May
NZ$1,535
includes taxes & fees
7 May - 8 May
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$196
Highest Price
NZ$1,590
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$227 per night from 28 Apr to 29 Apr
NZ$227
includes taxes & fees
28 Apr - 29 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
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
The price is NZ$196 per night from 4 May to 5 May
NZ$196
includes taxes & fees
4 May - 5 May
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Express Southington by IHG
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
The price is NZ$353 per night from 6 May to 7 May
NZ$353
includes taxes & fees
6 May - 7 May
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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Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is NZ$259 per night from 13 May to 14 May
NZ$259
includes taxes & fees
13 May - 14 May
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Cambria Hotel New Haven University Area
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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.