Guilford Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Guilford Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Surfside Hotel
Lordship
CA $1,077
per person
Nov 26 - Nov 30
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (222 reviews)
More of a b&b feel of an old renovated motel. No closets, counters, desks or dressers. Basically just beds and a bathroom. Clean but upstairs rooms smell like there was a fire at some point. Attached restaurant and bar is very convenient and food was very good.
Reviewed on Oct 11, 2026
Ready to book your vacation to Guilford?
Guilford Hotel Deals
Spark by Hilton Guilford
300 Boston Post Rd Guilford CT
CA $130
CA $149 total
Nov 9 - Nov 10
includes taxes & fees
9/10 Wonderful! (217 reviews)
"Excellent room! Clean and good breakfast!"
Reviewed on Oct 10, 2026
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
CA $173
CA $199 total
Oct 27 - Oct 28
includes taxes & fees
9.2/10 Wonderful! (2,391 reviews)
"Spacious room, great location! Didn’t like the noisy bathroom fan and air conditioner."
Reviewed on Oct 14, 2026
Motel 6 Milford, CT
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
CA $100
CA $114 total
Oct 27 - Oct 28
includes taxes & fees
6.6/10 (1,055 reviews)
"The hotel is an apartment building basically drug deals in the parking lot police literally patrol the area constantly. The font desk is a joke. People are hanging around the lobby and outside. My impression is that this hotel is a half way house. I was talking to a person and he said he h1s been ..."
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.
Stay near popular Guilford attractions
Guilford Town Green
Explore the great outdoors at Guilford Town Green, a lovely green space in Guilford. While in this family-friendly area, you can enjoy the restaurants.
Bishops Orchard and Winery
8.4/10 (11 reviews)
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.
Sachem Head Harbor
You can learn about the history of Guilford with a visit to Sachem Head Harbor. While in this family-friendly area, you can enjoy the restaurants.
beach near Sachem Head
Why not spend a lazy afternoon at beach near Sachem Head during your trip to Guilford? While in this family-friendly area, you can enjoy the restaurants.
Chaffinch Island State Park
9.6/10 (4 reviews)
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.
Guilford Art Center
9.2/10 (5 reviews)
Enjoy an outing to Guilford Art Center during your stay in Guilford. Take in the art scene in this relaxing area.
Hyland House Museum
8.8/10 (3 reviews)
You can spend an afternoon browsing the exhibits at Hyland House Museum in Guilford. Take in the art scene in this relaxing area.
beach near Chaffinch Island State Park
Why not spend a lazy afternoon at beach near Chaffinch Island State Park during your trip to Guilford? While in this family-friendly area, you can enjoy the restaurants.
Frequently asked questions
How much does a Guilford vacation package cost?
You'll find cheap prices from CA $986 on Expedia for your Guilford break. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Guilford costs.
What are the cheapest months to go to Guilford?
If you're looking to book a cheap Guilford vacation package, consider visiting in January, February and March. You'll generally find better prices on flights and accommodations during these quieter months — perfect for a budget-friendly break.
How many days is enough for Guilford?
You can easily visit all the main sights in Guilford in a few days, including the must-see Orchard Hill Plaza Shopping Centre. If you're after a longer Guilford vacation, check out what sort of activities and excursions are available in the area.
Is it worth booking a vacation package to Guilford?
During your Guilford vacation, you can count on experiencing some excellent nature and history. Leave enough room in your itinerary to explore major sights like Bishops Orchard and Winery and Guilford Art Centre.
How to find the best Guilford package deals?
Bagging a cheap Guilford package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply a couple of filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Guilford package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Guilford vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking hotels and flights separately. Better still, you can tailor your Guilford escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Guilford?
If you're considering a spontaneous Guilford trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Guilford?
- Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Guilford.
- Plan your budget wisely: In addition to the cost of your stay, you'll need to consider other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Guilford.
- Work out your trip length: Consider how long you'd like to spend discovering Guilford. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Guilford vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
