Guilford Vacations from $197

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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
Price was $261, price is now $197 per person
$197
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (1,092 reviews)
Comfortable and quiet

Reviewed on Sep 23, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $1,985, price is now $1,206 per person
$1,206
per person
Nov 6 - Nov 10
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
No reviews
Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
Price was $278, price is now $208 per person
$208
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (434 reviews)
Went for a wedding and was stranded at the venue from the hotel! It wasn’t until I threatened them with a lawsuit and amazingly they found a way to get back to the venue but that was after I spent $40 on an Uber. The hotel was nice but extremely noisy with the highway right next door. If you build a hotel next to a highway you should sound proof your property!!

Reviewed on Sep 18, 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 $280, price is now $212 per person
$212
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (1,005 reviews)
Convenient to airport. Stayed overnight for a flight. Hotel is as expected. Staff at check in was a bit difficult to understand with hearing issues. One slight issue with our room key not working but otherwise would stay again in the future for airport closeness.

Reviewed on Sep 22, 2025

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
Price was $771, price is now $589 per person
$589
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
8.8/10 Excellent! (1,783 reviews)
Room seemed a little outdated and didn't match pictures I saw before booking the room.

Reviewed on Sep 25, 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
$135 nightly
The price is $155 total per night from Oct 5 to Oct 6
$155 total
Oct 5 - Oct 6
Total with taxes and fees
8.4/10 Very Good! (32 reviews)
Good, clean and has been updated
"Easy check-in and out. Friendly staff. Good location for what we needed. TV never worked but was not an issue for us. Breakfast offerings were somewhat limited but not a deal breaker. Would stay again."

Reviewed on Sep 23, 2025

Spark by Hilton Guilford
Red Roof Inn PLUS+ & Suites Guilford

Red Roof Inn PLUS+ & Suites Guilford

2.5 out of 5
2300 Boston Post Rd, Guilford, CT
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $138 total per night from Sep 28 to Sep 29
$138 total
Sep 28 - Sep 29
Total with taxes and fees
7/10 Good! (411 reviews)
"I had a large, clean room and check in was easy. The refrigerator in the room was very loud. The rooms also have hardwood floors and the people upstairs were incredibly loud."

Reviewed on Jul 4, 2025

Red Roof Inn PLUS+ & Suites Guilford
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $183 total per night from Oct 12 to Oct 13
$183 total
Oct 12 - Oct 13
Total with taxes and fees
8.4/10 Very Good! (1,012 reviews)
"Great location good view"

Reviewed on Sep 24, 2025

Omni New Haven Hotel at Yale
See all 1,664 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 $197 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

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.