Guilford Vacations from $376

Book a Hotel + Flight or Car together to unlock savings

Your Guilford Vacation

With all the details organized before you take off, our Guilford vacation packages mean you can focus more on enjoying your getaway. No matter if you're based in the neighborhood of Madison Center, which is good for golfing, or somewhere else, this fun city promises an array of discoveries. If taking in sights is part of the plan during your trip to Guilford, swing by top attractions like Bill Miller’s Castle, Bishops Orchard and Winery and Guilford Art Center. A couple of clicks is all it takes to put together your ideal Guilford vacation on Expedia.

The Latest Guilford vacation packages

Price found within the past 48 hours. Click for updated prices.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $489, price is now $376 per person
$376
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (2,167 reviews)
Always feel back home when I see the smiles of the front desk staffs. Great location, convenient to everything! Clean rooms with decent space for travelers like me.

Reviewed on Jun 16, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,524, price is now $1,102 per person
$1,102
per person
Jul 20 - Jul 23
found 17 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
No reviews
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $1,166, price is now $867 per person
$867
per person
Jul 17 - Jul 19
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.6/10 Exceptional! (78 reviews)
Everything was PERPECT!

Reviewed on Jun 13, 2026

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Price was $827, price is now $643 per person
$643
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
2/10 (1 review)
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $636, price is now $499 per person
$499
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (31 reviews)
Great stay with many amenities to enjoy within the building!

Reviewed on Apr 3, 2026

Don't see what you're looking for?
See all available trips from Columbus to Guilford
View all trips

Stay near popular Guilford attractions

Guilford Town Green

The Guilford Town Green, one of New England's largest historic commons, offers shade trees perfect for relaxation. Explore surrounding boutiques or time your visit for farmers' markets and summer concerts.
See properties

Guilford Hotel Deals

Spark by Hilton Guilford

Spark by Hilton Guilford

2.5 out of 5
300 Boston Post Rd Guilford CT
$119 nightly
The price is $136 total per night from Jun 24 to Jun 25
$136 total
Jun 24 - Jun 25
Total with taxes and fees
9/10 Wonderful! (141 reviews)
"The room was good. It's a glorified motel. They lost me when I was told that I need to pay for Wi-Fi. They also put me next to the elevator. Every time it stopped there was a bell I could hear. Why ? "I see that you paid through a third party"."

Reviewed on Jun 16, 2026

Spark 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
$124 nightly
The price is $143 total per night from Jul 4 to Jul 5
$143 total
Jul 4 - Jul 5
Total with taxes and fees
9.2/10 Wonderful! (2,197 reviews)
"Always feel back home when I see the smiles of the front desk staffs. Great location, convenient to everything! Clean rooms with decent space for travelers like me."

Reviewed on Jun 16, 2026

New Haven Hotel
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Fully refundable
$72 nightly
The price is $83 total per night from Jun 22 to Jun 23
$83 total
Jun 22 - Jun 23
Total with taxes and fees
7.2/10 Good! (1,023 reviews)
"Exactly what I was looking for and an incredibly pleasant stay for a business trip, cheers!"

Reviewed on Jun 15, 2026

Motel 6 New Haven - Branford, CT
See all 1,756 properties in Guilford
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.

Find the Best Guilford Vacation Packages

Guilford Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
22,500
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Hammonasset Beach State Park, East Haven Town Beach and Hammonasset Beach

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Guilford vacation package cost?
Offering excellent value package deals from $376 on Expedia, you'll be thrilled with how little a vacation to Guilford costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Guilford?
If you're hoping to snag a cheap Guilford vacation package, consider traveling in November, December and January. You'll usually find better rates on hotels and flights during these months — perfect for travelers wishing to save money.
How many days is enough for Guilford?
You can visit all the major attractions in Guilford within a few days, including the popular Hyland House Museum. If you're looking for a longer Guilford vacation, look at what kind of activities and day trips are available in the area.
Is it worth booking a vacation package to Guilford?
Whether you're planning to check out attractions like Bishops Orchard and Winery and Guilford Art Center, or want to experience its terrific nature and history, a Guilford vacation guarantees an unforgettable adventure. Book your getaway with Expedia and find out why Guilford is such a good vacation destination.
How to find the best Guilford package deals?
Use Expedia's handy filters to find some fabulous Guilford package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Guilford package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Guilford vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights separately. Better still, you can customize your Guilford escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Guilford?
If you have your Guilford vacation dates locked in, book as early as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for traveling on a whim.
Does Expedia offer Book Now, Pay Later Guilford vacation packages?
If you're anything like us, you love going away but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Guilford break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.