Guilford Vacations from $274

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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.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Oct 8 - Oct 10
found 1 day ago
Roundtrip flight included
Detroit (DTT) to New Haven (HVN)
8.8/10 Excellent! (1,002 reviews)
I had made reservation after midnight while tired on the road, needing a place to sleep, the night manager fixed my reservation so I could get a room immediately. Super helpful and much appreciated.

Reviewed on Jul 23, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Sep 18 - Sep 23
found 22 hours ago
Roundtrip flight included
Detroit (DTT) to New Haven (HVN)
8.8/10 Excellent! (1,023 reviews)
I inadvertently booked 2 reservations because the first one did not go thru properly. I feel they should have informed me about this before my arrival. I have received a cancellation notice. I want to make sure I am only. Barged for one room and a one night stay.

Reviewed on Jul 31, 2025

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 23
found 22 hours ago
Roundtrip flight included
Detroit (DTT) to New Haven (HVN)
8.6/10 Excellent! (550 reviews)
Check in girl was great.

Reviewed on Jul 26, 2025

The Surfside Hotel

The Surfside Hotel

2 out of 5
Lordship
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
9.2/10 Wonderful! (118 reviews)
I love the access to the beach and to convince of the restaurant downstairs.

Reviewed on Jul 27, 2025

Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
per person
Oct 8 - Oct 10
found 1 day ago
Roundtrip flight included
Detroit (DTT) to New Haven (HVN)
8.8/10 Excellent! (412 reviews)
Everything was good

Reviewed on Jul 25, 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

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
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $146 total per night from Aug 31 to Sep 1
$146 total
Aug 31 - Sep 1
Total includes taxes and fees
8.2/10 Very Good! (11 reviews)
Beach stay with Spark
"It was a beach getaway stay. Close to the State park/ beach. Very nice way to end the day at the beach. Hotel has every needed amenity. Staff is friendly and informative about the area."

Reviewed on Jul 27, 2025

Spark by Hilton Guilford
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 Aug 7 to Aug 8
$83 total
Aug 7 - Aug 8
Total includes taxes and fees
6.8/10 (1,002 reviews)
"Good place"

Reviewed on Jul 29, 2025

Motel 6 New Haven - Branford, CT
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $152 total per night from Aug 11 to Aug 12
$152 total
Aug 11 - Aug 12
Total includes taxes and fees
8.8/10 Excellent! (1,685 reviews)
"Very nice hotel but the control panel for ac did not work properly"

Reviewed on Jul 31, 2025

New Haven Hotel
See all 1,673 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.

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Frequently asked questions

How much does a Guilford vacation package cost?
Offering excellent value package deals from $274 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.