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 $710, price is now CA $627 per person
CA $627
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
7/10 Good! (931 reviews)
We got in and had to wait nearly half an hour with small kids for the receptionist to show up to check us in. Then I was bitten by bed bugs.

Reviewed on Jul 9, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $893, price is now CA $741 per person
CA $741
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8/10 Very good! (1,001 reviews)
Still the same wonderful little place as the last time I stayed here!

Reviewed on Jul 11, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,060, price is now CA $1,733 per person
CA $1,733
per person
Aug 11 - Aug 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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 $946, price is now CA $900 per person
CA $900
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
7.6/10 Good! (1,007 reviews)
Good hotel, especially for the price

Reviewed on Jul 10, 2026

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
Price was CA $751, price is now CA $721 per person
CA $721
per person
Aug 31 - Sep 4
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7.8/10 Good! (1,003 reviews)
Good stay accommodating, Staff

Reviewed on Jun 30, 2026

Ready to book your vacation to Guilford?

 

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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
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Jul 27 to Jul 28
CA $161
CA $186 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (157 reviews)
"Clean,well kept room. Nice bathroom, comfortable sorroundings."

Reviewed on Jul 10, 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 $167 per night from Jul 26 to Jul 27
CA $167
CA $193 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (2,217 reviews)
"The hotel feels a bit old and outdated. Service is basic and not particularly attentive."

Reviewed on Jul 10, 2026

New Haven Hotel
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Jul 19 to Jul 20
CA $146
CA $168 total
Jul 19 - Jul 20
includes taxes & fees
8/10 Very good! (1,718 reviews)
"Room was clean, parking was easy. The only complaint in which the hotel cannot remedy is the high traffic sounds from the highway."

Reviewed on Jul 10, 2026

Best Western Executive Hotel Of New Haven - West Haven
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 $627 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.