Middlefield Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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 Middlefield Vacation
Prepare to experience Middlefield on your terms with a custom Middlefield vacation package! Discovering the best parts of this captivating city is simple with a base in a neighborhood such as Washington Street Historic District, which is great for history, among many other things. Wesleyan University, Powder Ridge Mountain Park and Resort and Brownstone Exploration & Discovery Park are just a few of the many sights you'll want to check out during your trip to Middlefield. No matter your travel plans or the size of your budget, organizing your ultimate tailored Middlefield vacation is a cinch with Expedia.
Top Middlefield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Milford - New Haven
Price was CA $1,217, price is now CA $1,172 per person
CA $1,172
per person
Jun 27 - Jul 1
found 18 hours ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
7/10 Good! (1,003 reviews)
The ice machine wasn't working. Neither one. Bur the staff was so nice!! It was clean and close to everything.. I will definitely stay there again.
Reviewed on Apr 12, 2026
Springhill Suites Milford
Price was CA $1,567, price is now CA $1,527 per person
CA $1,527
per person
Jun 27 - Jul 1
found 18 hours ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
8.6/10 Excellent! (1,000 reviews)
Clean modern room. Spacious bathroom. Staff very friendly. Nice selection for breakfast.
Reviewed on Apr 8, 2026
Middlefield Hotel Deals
New Haven Hotel
229 George Street New Haven CT
Fully refundable
The price is CA $168 per night from May 3 to May 4
CA $168
CA $194 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (2,090 reviews)
The
Reviewed on Apr 13, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundable
The price is CA $149 per night from May 3 to May 4
CA $149
CA $172 total
May 3 - May 4
includes taxes & fees
8.6/10 Excellent! (1,271 reviews)
Goid complete breakfast, property was maintained , room was clean , but the hallway 2nd floor had a terrible bad fish smell! From elevators all the way down to end of hall to my room - terrible smell, i informed front desk- they dont have a clue- something fishy nasty smelling!
Reviewed on Apr 12, 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Apr 26 to Apr 27
CA $119
CA $137 total
Apr 26 - Apr 27
includes taxes & fees
7.6/10 Good! (1,237 reviews)
Convenient and clean. Staff was friendly and gave great suggestions.
Reviewed on Apr 13, 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.
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.
