Book Holiday Homes in Guilford

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Featured Holiday Homes in Guilford

Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton CT
Stay at this holiday home in Clinton. Enjoy a garden, laundry facilities and patios. Popular attractions Adam Stanton House and General Store Museum and Indian ...
Opens in a new windowLarge Charming Historic House close to Beaches
Aqua Vista

Aqua Vista

Greenport, NY
Stay at this holiday home in Greenport. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Railroad Museum of Long Island and East End Seaport ...
Opens in a new windowAqua Vista
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

New Britain CT
The price is NZ$428 per night from 7 Dec to 8 Dec
NZ$428
7 Dec - 8 Dec
includes taxes & fees
Stay at this holiday home in New Britain. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions New Britain Stadium and New Britain Youth Museum ...
Opens in a new windowClean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
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Gorgeous 4BR Beach House with Private Beach Access.

Gorgeous 4BR Beach House with Private Beach Access.

Branford CT
Stay at this holiday home in Branford. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Foote Memorial Park Tennis Center and Stony Creek ...
Opens in a new windowGorgeous 4BR Beach House with Private Beach Access.
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Guilford CT
Stay at this holiday home in Guilford. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Chaffinch Island State Park and Guilford Town Green ...
Opens in a new windowA TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Old Lyme CT
Stay at this beach holiday home in Old Lyme. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Lyme Academy of Fine Arts and Rocky ...
Opens in a new windowBeachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
Private Apartment  in Berlin

Private Apartment in Berlin

2 out of 5
Berlin CT
The price is NZ$533 per night from 6 Jan to 7 Jan
NZ$533
6 Jan - 7 Jan 2026
includes taxes & fees
Stay at this holiday home in Berlin. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions New Britain Stadium and New Britain Museum ...
Opens in a new windowPrivate Apartment in Berlin
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Milford CT
Stay at this beach holiday home in Milford. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Robert Treat Farm and Bowlero Milford are located ...
Opens in a new windowBeach Front Arts & Crafts House With Gorgeous Views Of The Sound
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Branford CT
Stay at this holiday home in Branford. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Foote Memorial Park Tennis Center ...
Opens in a new windowBEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
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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
535 Holiday Homes
Lowest Price
NZ$157
Highest Price
NZ$533
Popular accommodation
Large Charming Historic House close to Beaches, Aqua Vista , Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage, Gorgeous 4BR Beach House with Private Beach Access., A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!, Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!, Private Apartment in Berlin, Beach Front Arts & Crafts House With Gorgeous Views Of The Sound, BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Top trending hotels in Guilford

Spark by Hilton Guilford

Spark by Hilton Guilford

2.5 out of 5
300 Boston Post Rd Guilford CT
Fully refundableReserve now, pay when you stay
The price is NZ$187 per night from 12 Dec to 13 Dec
NZ$187
12 Dec - 13 Dec
includes taxes & fees
Stay at this business-friendly hotel in Guilford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowSpark by Hilton 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 NZ$235 per night from 18 Dec to 19 Dec
NZ$235
18 Dec - 19 Dec
includes taxes & fees
Stay at this business-friendly hotel in New Haven. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff and the ...
Opens in a new windowNew Haven Hotel
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Fully refundable
The price is NZ$205 per night from 28 Dec to 29 Dec
NZ$205
28 Dec - 29 Dec
includes taxes & fees
Stay at this business-friendly hotel in New Haven. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff and the ...
Opens in a new windowCambria Hotel New Haven University Area
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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$157 per night from 4 Jan to 5 Jan
NZ$157
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Southington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowHoliday Inn Express Southington by IHG
Don't see what you're looking for?
See all available properties in Guilford
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.