Guilford Vacations from $797
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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.
Landing Apartments New Haven Near Dixwell
Newhallville
$1,025
per person
Nov 24 - Dec 1
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.
Reviewed on May 25, 2026
Hyatus Luxury Residences City Crossing
The Hill
$1,306
per person
Nov 24 - Dec 1
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (34 reviews)
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.
Reviewed on Aug 10, 2026
Stay near popular Guilford attractions
Guilford Town Green
The Guilford Town Green, one of New England's largest historic commons, offers shade trees perfect for relaxation. Explore surrounding boutiques or time your visit for farmers' markets and summer concerts.
Bishops Orchard and Winery
8.4/10 (11 reviews)
This historic family farm has cultivated Connecticut's finest fruits since 1871. Sample estate-made wines, pick seasonal berries, or browse the market's fresh produce and artisanal goods.
Chaffinch Island State Park
9.6/10 (4 reviews)
This serene 22-acre coastal park offers picturesque views of Long Island Sound and rocky shores to explore. Bring binoculars for exceptional birdwatching while enjoying the peaceful tidal pools and grassy picnic areas.
Guilford Art Center
9.2/10 (5 reviews)
This creative hub offers classes in ceramics, blacksmithing, painting, and jewelry making for all skill levels. Explore the gallery's rotating exhibits or find unique handcrafted treasures in the artisan shop.
Henry Whitfield State Museum
10.0/10 (3 reviews)
Built in 1639, this stone house stands as Connecticut's oldest dwelling and New England's oldest stone home. Explore three floors of period furnishings that showcase nearly four centuries of fascinating American history.
Sachem Head Harbor
This serene coastal harbor showcases New England's maritime heritage with its historic yacht club dating to the 19th century. Enjoy panoramic water views while watching sailboats glide across the picturesque bay.
Hyland House Museum
8.8/10 (3 reviews)
This beautifully preserved 1713 saltbox house showcases colonial life through period furnishings. Guided tours reveal historical details while surrounding gardens complement your journey.
Medad Stone Tavern Museum
Find out about the history of Guilford when you take a trip to Medad Stone Tavern Museum. While in this family-friendly area, you can enjoy the restaurants.
Guilford Hotel Deals
Spark by Hilton Guilford
300 Boston Post Rd Guilford CT
Fully refundableReserve now, pay when you stay
$116 nightly
$133 total
Sep 21 - Sep 22
Total with taxes and fees
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$135 nightly
$155 total
Sep 27 - Sep 28
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$91 nightly
$104 total
Sep 21 - Sep 22
Total with taxes and fees
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 $797 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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- Chaffinch Island State Park
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- Double Beach
- Hyland House Museum
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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.
