Book Holiday Homes in Guilford

February 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday

March 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Guilford

Enjoy Autumn with us.

Enjoy Autumn with us.

Southold
Stay at this vacation home in Southold. Enjoy free WiFi, a garden, and patios. Popular attractions The Old Field Vineyards and Sparkling Pointe are located ...
Enjoy Autumn with us.
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!
McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale

West Haven
Book a stay at this family-friendly vacation home in West Haven. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Connecticut ...
McAngel Haven: 5 mins from Yale
Save an average of 15% on thousands of hotels when you're signed in
Amazing Lakefront Property

Amazing Lakefront Property

Middlefield
Stay at this vacation home in Middlefield. Enjoy free WiFi, a garden, and patios. Popular attractions Lake Beseck Beach and Powder Ridge Mountain Park and Resort ...
Amazing Lakefront Property
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Riverhead
The price is NZ$1,644 per night from 2 Mar to 3 Mar
NZ$1,644
includes taxes & fees
2 Mar - 3 Mar
Stay at this vacation home in Riverhead. Enjoy patios, in-room jetted tubs, and an in-room coffeemaker. Popular attractions Roanoke Vineyards and Baiting Hollow ...
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
NEW-Another Fun Downtown Location 1st floor

NEW-Another Fun Downtown Location 1st floor

2 out of 5
Southington
Stay at this vacation home in Southington. Enjoy a water park, an in-room coffeemaker, and air conditioning. Popular attractions Barnes Museum and Southington ...
NEW-Another Fun Downtown Location 1st floor
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Durham
Stay at this vacation home in Durham. Enjoy free WiFi, a garden, and patios. Popular attractions Millers Pond State Park and Dooley Pond Public Access are located ...
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Bright Milford Beach House w/ Outdoor Shower

Bright Milford Beach House w/ Outdoor Shower

Milford
Book a stay at this beach vacation home in Milford. Enjoy a beach locale, a garden, and patios. Popular attractions Pond Point Beach and Bayview Beach are located ...
Bright Milford Beach House w/ Outdoor Shower
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Guilford Center
Book a stay at this family-friendly vacation home in Guilford. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Chaffinch Island State Park ...
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Don't see what you're looking for?
See all available properties in Guilford
View all properties
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
471 Holiday Homes
Lowest Price
NZ$175
Highest Price
NZ$1,644
Popular accommodation
Enjoy Autumn with us., Cozy Westbrook Vacation Rental - Walk to Beach!, McAngel Haven: 5 mins from Yale, Amazing Lakefront Property, Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons, NEW-Another Fun Downtown Location 1st floor, New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown., Bright Milford Beach House w/ Outdoor Shower, Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

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 NZ$237 per night from 16 Mar to 17 Mar
NZ$237
includes taxes & fees
16 Mar - 17 Mar
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
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 NZ$303 per night from 17 Mar to 18 Mar
NZ$303
includes taxes & fees
17 Mar - 18 Mar
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Omni New Haven Hotel at Yale
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$220 per night from 16 Mar to 17 Mar
NZ$220
includes taxes & fees
16 Mar - 17 Mar
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
Save an average of 15% on thousands of hotels when you're signed in
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Fully refundableReserve now, pay when you stay
The price is NZ$175 per night from 9 Mar to 10 Mar
NZ$175
includes taxes & fees
9 Mar - 10 Mar
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Executive Hotel Of New Haven - West Haven
Don't see what you're looking for?
See all available properties in Guilford
View all properties
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.