Guilford Vacations from $216

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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
Price was $278, price is now $216 per person
$216
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (1,018 reviews)
Access to airport and service for my early Lyft was great

Reviewed on Oct 17, 2025

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $1,035, price is now $726 per person
$726
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (1,164 reviews)
The staff was very friendly and helpful. There aren't any restaurants within walking distance, but they do have an option to order out that was pretty good. The one thing that surprised me about the room was that the furniture upholstery was somewhat tattered. I don't ever recall seeing that in a Hyatt property before.

Reviewed on Oct 15, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $1,068, price is now $793 per person
$793
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (889 reviews)
The bar downstairs is so fun, and their pizza night provided us with the best pizza in New Haven (better than the famous spots we all know). The bartenders made our trip, and showed us the warmth of the people of New Haven. Do not skip the bar! Even if you do not drink, the games are great and the food is even better.

Reviewed on Oct 17, 2025

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 $1,343, price is now $1,029 per person
$1,029
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (54 reviews)
Wonderful property- brand new building, nice spacious rooms perfect for family. Instructors for check in and out and everything in between very clear and helpful.

Reviewed on Oct 15, 2025

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $492, price is now $383 per person
$383
per person
Nov 25 - Nov 29
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (575 reviews)
Didn't get a chance to enjoy the breakfast or pool as intended, however customer service and cleanliness was outstanding! Plus they gave a small welcome bag with some water and little treats/snacks! Parking was easy, and location even though was by highway, was relatively quiet!

Reviewed on Oct 11, 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
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $130 total per night from Nov 2 to Nov 3
$130 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (43 reviews)
"Great"

Reviewed on Oct 12, 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
$70 nightly
The price is $81 total per night from Oct 23 to Oct 24
$81 total
Oct 23 - Oct 24
Total with taxes and fees
7/10 Good! (1,017 reviews)
"Easy to get to, clean and affordable. The pizza bar at the end of the property is huge plus. Could use a hair dryer or coffee in the room but considering the price still an excellent choice."

Reviewed on Oct 11, 2025

Motel 6 New Haven - Branford, CT
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
$98 nightly
The price is $113 total per night from Nov 16 to Nov 17
$113 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (1,119 reviews)
"The front and interior of the building is beautiful. The back parking lot was a bit overgrown and the rear entry didnt close automatically. Otherwise, a clean, comfortable place to sleep after a long day."

Reviewed on Oct 12, 2025

Holiday Inn Express Southington by IHG
See all 1,651 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.

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 $216 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.