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.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
Price was CA $595, price is now CA $555 per person
CA $555
per person
Aug 9 - Aug 12
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7/10 Good! (929 reviews)
Good area and served purpose for the price. Rooms could use some cosmetic updates.

Reviewed on Jul 6, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $717, price is now CA $619 per person
CA $619
per person
Aug 9 - Aug 12
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very good! (1,001 reviews)
Lage room, Clean and comfortable bed. Bathroom could use updating and an elevated toilet seat. Staff very nice. Would stay again.

Reviewed on Jul 7, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,037, price is now CA $1,873 per person
CA $1,873
per person
Aug 6 - Aug 9
found 11 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
No reviews

Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

3 out of 5
Price was CA $1,012, price is now CA $963 per person
CA $963
per person
Aug 14 - Aug 17
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
7.6/10 Good! (1,010 reviews)
The property is in the middle of upgrading...but it's quiet and location was perfect for me

Reviewed on Jul 5, 2026

Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

2.5 out of 5
Price was CA $942, price is now CA $911 per person
CA $911
per person
Aug 14 - Aug 17
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
6.8/10 (1,010 reviews)
I had booked a queen bed room at a lower price. I was given a king bed at much higher price

Reviewed on Jul 4, 2026

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Guilford Hotel Deals

Spark by Hilton Guilford

Spark by Hilton Guilford

2.5 out of 5
300 Boston Post Rd Guilford CT
The price is CA $162 per night from Jul 13 to Jul 14
CA $162
CA $186 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (153 reviews)
"Breakfast was great and appreciated when you don't know the area just yet! Great muffins, yogurt and bagels!"

Reviewed on Jul 6, 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
The price is CA $168 per night from Jul 26 to Jul 27
CA $168
CA $193 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (2,207 reviews)
"There was no complimentary coffee ( which is advertised in the hotel) this morning or bagels for breakfast. I was told by an employee that the “ran out”. However, they are delivered from an offsite location daily. I asked if I could get a cup of the “ gourmet” coffee from the Starbucks machine instead ..."

Reviewed on Jul 6, 2026

New Haven Hotel
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Jul 20 to Jul 21
CA $92
CA $106 total
Jul 20 - Jul 21
includes taxes & fees
6.6/10 (1,016 reviews)
"I enjoy my stay there very good but hard to get to places around the area for eating and dining."

Reviewed on Jul 6, 2026

Motel 6 Milford, CT
See all 1,744 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.
All Inclusive Vacations
All Inclusive Vacations
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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.
See properties

Frequently asked questions

How much does a Guilford vacation package cost?
You'll find cheap prices from CA $555 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

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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.