Guilford Vacations from $287

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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.
Sleep Inn & Suites Niantic

Sleep Inn & Suites Niantic

2.5 out of 5
Price was $364, price is now $287 per person
$287
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
8.4/10 Very Good! (1,008 reviews)
Clean room. Good value for the money.

Reviewed on Nov 17, 2025

Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area

2.5 out of 5
Price was $407, price is now $311 per person
$311
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9/10 Wonderful! (398 reviews)
yes, very well maintianed

Reviewed on Nov 11, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $623, price is now $490 per person
$490
per person
Jan 29 - Feb 2
found 15 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
17.6/10 Exceptional! (1,004 reviews)
Great and clean place to stay in

Reviewed on Nov 16, 2025

Comfort Inn Naugatuck-Shelton, CT

Comfort Inn Naugatuck-Shelton, CT

2.5 out of 5
Price was $419, price is now $330 per person
$330
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
7.8/10 Good! (713 reviews)
Front desk and service were great, but the room could have been in cleaner

Reviewed on Nov 2, 2025

Homewood Suites by Hilton Southington, CT

Homewood Suites by Hilton Southington, CT

3 out of 5
Price was $507, price is now $404 per person
$404
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
18.4/10 Exceptional! (1,003 reviews)
Great staff, clean rooms

Reviewed on Nov 17, 2025

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Discover the most popular places to visit in Guilford

Bishops Orchard and Winery

You can enjoy a tasting or tour at Bishops Orchard and Winery during your travels to Guilford. While you're here, you can savor the top-notch restaurants.

Bishops Orchard and Winery

Hyland House Museum

You can spend an afternoon browsing the exhibits at Hyland House Museum in Guilford. Take in the art scene in this relaxing area.

Hyland House Museum

Chaffinch Island State Park

Commune with nature and explore the great outdoors at Chaffinch Island State Park during your travels in Guilford. Take in the art scene and stargazing spots in this relaxing area.

Chaffinch Island State Park

Guilford Hotel Deals

Spark by Hilton Guilford

Spark by Hilton Guilford

2.5 out of 5
300 Boston Post Rd Guilford CT
$90 nightly
The price is $104 total per night from Dec 7 to Dec 8
$104 total
Dec 7 - Dec 8
Total with taxes and fees
8.6/10 Excellent! (51 reviews)
The room was perfect, the beds were amazing, and the staff was top notch.

Reviewed on Nov 10, 2025

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
$89 nightly
The price is $103 total per night from Dec 18 to Dec 19
$103 total
Dec 18 - Dec 19
Total with taxes and fees
9/10 Wonderful! (1,870 reviews)
Always happy to be there! Great staff and convenient location, perfect for a short stay on campus.

Reviewed on Nov 8, 2025

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
$83 nightly
The price is $95 total per night from Nov 23 to Nov 24
$95 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,149 reviews)
The room was great and the staff was really helpful...

Reviewed on Nov 7, 2025

Holiday Inn Express Southington by IHG
See all 1,666 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

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Frequently asked questions

How much does a Guilford vacation package cost?
Offering excellent value package deals from $287 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.

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