Guilford Vacations from $413
Book a Hotel + Flight or Car together to unlock savings
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.
Hyatus Luxury Residences City Crossing
The Hill
$413
per person
Dec 4 - Dec 6
found 22 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (34 reviews)
Fast and effective check-in, great amenities in the building. Kitchen well furnished.
Overall great experience.
Reviewed on Oct 11, 2026
Landing Apartments New Haven Near Dixwell
Newhallville
$512
per person
Dec 4 - Dec 6
found 22 hours ago
Roundtrip non-stop 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
Stay near popular Guilford attractions
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.
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.
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.
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.
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
$91 nightly
$105 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (218 reviews)
"Clean room especially for a room that allows dogs. :)"
Reviewed on Oct 14, 2026
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$127 nightly
$146 total
Oct 27 - Oct 28
Total with taxes and fees
Motel 6 Milford, CT
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
$70 nightly
$80 total
Nov 5 - Nov 6
Total with taxes and fees
6.6/10 (1,051 reviews)
"We arrived on a pouring rainy day. Staff was great, got into our room and right away I noticed it needed some updating. No coffee maker in the room, had to ask for extra towels and wash clothes even though it was booked for 3 people. Room was clean and beds had clean sheets. Pool and gym signs were ..."
Reviewed on Oct 14, 2026
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
What's the best vacation package for Guilford?
Guilford's appeal for romantic getaways means the best vacation packages in Guilford often center on a comfortable base for exploring the charming coastal area. A package with a stay at Spark by Hilton Guilford, rated 8.2 out of 10, places you about 1 mile from central Guilford and about 5 miles from Hammonasset Beach State Park. Travelers frequently praise the friendly staff and the spacious rooms, making it a pleasant choice for couples.For travelers seeking a comfortable and value-focused Guilford vacation package, consider a stay at Red Roof Inn PLUS+ & Suites Guilford. Located about 3 miles from central Guilford, this hotel offers free breakfast, free WiFi, and rooms with kitchenettes, providing added convenience. Guests often highlight the great staff and comfortable overall experience.
How can I save money on a Guilford vacation package?
When you bundle, you can save up to 30%*. To save money on a Guilford package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
Is Guilford better suited for a beach vacation or a cultural trip?
Guilford is primarily a beach and outdoor destination, offering a relaxing Guilford vacation with scenic views and natural attractions. You can spend time at Hammonasset Beach State Park, about 13 miles from central Guilford, or explore the coastal beauty of Chaffinch Island State Park.Beyond its natural appeal, Guilford also has a rich historical and cultural side. The town is home to a notable collection of historic homes, including the Henry Whitfield House, which is the oldest stone house built by English settlers in North America. A Guilford vacation package can easily combine these outdoor pursuits with visits to cultural sites like the Guilford Art Center or the historic Guilford Town Green.
What are the top things to do in Guilford?
A Guilford vacation offers a mix of coastal relaxation, historical exploration, and local charm. Consider these top activities:Browse and book things to do in Guilford on Expedia.
Do you need to rent a car in Guilford, or is public transport enough?
For a Guilford vacation package, a rental car offers the most flexibility for exploring the area, especially since Guilford is a beach destination outside a major city. While the Shore Line East train provides service to nearby towns like New Haven and New London, and the Connecticut Transit S bus connects Guilford to New Haven, many of Guilford's attractions and scenic spots are spread out. Having a car allows you to easily reach places like Hammonasset Beach State Park, about 13 miles away, or the Bishops Orchard and Winery, about 2 miles from central Guilford. For Guilford vacation packages with flights, a car rental can be bundled to allow you to fully experience the region at your own pace.
Are Guilford vacation package hotels conveniently located?
Guilford vacation package hotels are generally conveniently located, offering easy access to the town center and nearby attractions. For instance, Spark by Hilton Guilford, rated 8.2 out of 10, is situated about 1 mile from central Guilford, and about 5 miles from Hammonasset Beach State Park. Similarly, Tower Inn And Suites Of Guilford - Madison is also about 1 mile from central Guilford, placing you close to local shops and dining. Even properties slightly further out, like Red Roof Inn PLUS+ & Suites Guilford, about 3 miles from the center, still provide good access to the area's sights. This means you can choose a Guilford vacation package that keeps you close to the heart of the town or offers a bit more space while remaining accessible.
Can I change or cancel my Guilford vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Guilford vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Guilford vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Guilford vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Guilford?
To find last-minute vacation packages to Guilford, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Guilford vacation packages?
Free cancellation on a Guilford vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Guilford vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Guilford getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Guilford vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.
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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.