Guilford Vacations from $411

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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.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to New Haven (HVN)
8.8/10 Excellent! (1,014 reviews)
It was clean staff was wonderful

Reviewed on Jul 2, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to New Haven (HVN)
8.4/10 Very Good! (1,003 reviews)
Great hotel. Will stay here again.

Reviewed on Jun 30, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to New Haven (HVN)
9.2/10 Wonderful! (824 reviews)
Room Cards are amazing and their pizza phone booth will have me coming back again

Reviewed on Jul 4, 2025

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to New Haven (HVN)
9.6/10 Exceptional! (16 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.

Reviewed on Jun 27, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to New Haven (HVN)
8.8/10 Excellent! (773 reviews)
Convenient location, excellent facility. Friendly staff.

Reviewed on Jul 5, 2025

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Discover the most popular places to visit in Guilford

Bishops Orchard and Winery

3/5(1 review)

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

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

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

Guilford Hotel Deals

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
$144 nightly
The price is $165 total per night from Jul 14 to Jul 15
$165 total
Jul 14 - Jul 15
Total includes taxes and fees
8.6/10 Excellent! (4 reviews)
"I wished you had some hair conditioner."

Reviewed on Jun 4, 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
$135 nightly
The price is $155 total per night from Jul 21 to Jul 22
$155 total
Jul 21 - Jul 22
Total includes taxes and fees
8.8/10 Excellent! (1,627 reviews)
"The property was very nice with great customer service.We stayed on a Friday night and we could hear the music from the night club behind the hotel late into the night. Other than that I have no complaints about the property."

Reviewed on Jul 3, 2025

New Haven Hotel
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Aug 3 to Aug 4
$116 total
Aug 3 - Aug 4
Total includes taxes and fees
7.4/10 Good! (1,013 reviews)
"It had a good vibe walking in, the only thing I disliked was the Queen size bed was definitely a full size bed, but was marked as a queen size bed."

Reviewed on Jul 1, 2025

Clarion Inn
See all 1,690 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 $411 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.