Guilford Vacation Packages
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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.
Top Guilford Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was CA $1,383, price is now CA $957 per person
CA $957
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
We have been coming here for years and it is the best it’s ever been! Staff is friendly and accommodating. The rooms have been renovated and clean.
Reviewed on May 17, 2026
Head of Pond House
Price was CA $3,985, price is now CA $3,270 per person
CA $3,270
per person
Jun 18 - Jun 21
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
10/10 Exceptional! (7 reviews)
Very special property. One of my favorites. Beautiful, exceptionally clean and in a gorgeous location. Host was exceptional and communication excellent.
Reviewed on May 9, 2026
The Scranton Seahorse Inn
Madison Center
Price was CA $2,011, price is now CA $1,785 per person
CA $1,785
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9/10 Wonderful! (242 reviews)
We had a wonderful stay. Perfect location, great staff, and check-in process, and our room was delightful.
Reviewed on Apr 22, 2026
Saybrook Point Resort & Marina
Old Saybrook Center
Price was CA $2,861, price is now CA $2,550 per person
CA $2,550
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.6/10 Exceptional! (1,002 reviews)
We ended up getting an upgrade into one of the two bedroom two bathroom pillows due to the renovation on the main hotel. We were pleasantly surprised we felt like we were home. It was so nice so relaxing. Everything was amazing and we could literally walk right across the street to get something to eat at fresh salt or at the choo-choo lounge views of the water at home field by having a full kitchen and laundry felt like a great little mini vacation we’ve been there before and we will be back again. Bravo.
Reviewed on May 17, 2026
Guilford Hotel Deals
Spark by Hilton Guilford
300 Boston Post Rd Guilford CT
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from May 31 to Jun 1
CA $168
CA $193 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (125 reviews)
"I stayed at the hotel for four nights and was pleasantly surprised with the room size, cleanliness, and comfort of the hotel, especially considering a very, very reasonable price. The whole area was very quiet and I slept with the windows opened, which is not a common thing anywhere:). It is a small ..."
Reviewed on May 18, 2026
TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12
Guilford CT
10/10 Exceptional! (43 reviews)
"Host was very communicative. The property was incredible and unique. One of the cozier spots I’ve stayed in. We loved every minute"
Reviewed on May 4, 2026
New Haven Hotel
229 George Street New Haven CT
The price is CA $174 per night from May 25 to May 26
CA $174
CA $200 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (2,140 reviews)
"Very clean and nice property. Uber does not go here and you have to use Lift."
Reviewed on May 19, 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.
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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.
