Guilford Vacations from $390

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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.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $468, price is now $390 per person
$390
per person
Mar 15 - Mar 18
found 4 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
clean room, helpful staff

Reviewed on Jan 4, 2026

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $613, price is now $490 per person
$490
per person
Mar 15 - Mar 18
found 4 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
Clean and nice! Really appreciated the bath robes.

Reviewed on Jan 2, 2026

Landing Modern 2bd, Gym

3 out of 5
West New Haven
Price was $739, price is now $592 per person
$592
per person
Mar 15 - Mar 18
found 4 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to New Haven (HVN)
No reviews
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Price was $926, price is now $749 per person
$749
per person
Mar 15 - Mar 18
found 4 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to New Haven (HVN)
9.6/10 Exceptional! (60 reviews)
Very clean, exactly as on website

Reviewed on Nov 2, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $556, price is now $454 per person
$454
per person
Mar 15 - Mar 18
found 4 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Great staff, convenient central location, and tasteful retro-collegiate decor in a renovated historic building.

Reviewed on Jan 1, 2026

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Discover the most popular places to visit in Guilford

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

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

Guilford Hotel Deals

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
$100 nightly
The price is $115 total per night from Jan 8 to Jan 9
$115 total
Jan 8 - Jan 9
Total with taxes and fees
7/10 Good! (431 reviews)
Very clean

Reviewed on Dec 8, 2025

Red Roof Inn PLUS+ & Suites Guilford
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
$101 nightly
The price is $116 total per night from Jan 31 to Feb 1
$116 total
Jan 31 - Feb 1
Total with taxes and fees
8.8/10 Excellent! (77 reviews)
The room was clean, check in was friendly and quick.

Reviewed on Jan 5, 2026

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
$102 nightly
The price is $118 total per night from Jan 25 to Jan 26
$118 total
Jan 25 - Jan 26
Total with taxes and fees
9/10 Wonderful! (1,988 reviews)
Customer service is top-notch, they are always very accommodating and friendly. We found the hotel to be very clean, the location is extremely convenient to dining shopping and the areas of New Haven. You would want to explore. Parking is extremely convenient and attached to the hotel. There are ...

Reviewed on Jan 4, 2026

New Haven Hotel
See all 1,704 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 $390 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.