Middlefield Vacation Packages

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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.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
Price was CA $729, price is now CA $727 per person
CA $727
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
7/10 Good! (917 reviews)
Just motel , clean. No breakfast there, no coffee either. At 10 AM nobody showed up into front office for check out.

Reviewed on Jan 1, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $936, price is now CA $734 per person
CA $734
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8/10 Very Good! (1,004 reviews)
Parking was easy. Bed mattress terrible. Tired room and furnishings. Basic supplies.

Reviewed on Apr 28, 2026

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
Price was CA $1,563, price is now CA $1,540 per person
CA $1,540
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.6/10 Exceptional! (1,001 reviews)
Everything was super clean and staff was friendly and helpful.

Reviewed on Apr 14, 2026

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Middlefield Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
The price is CA $173 per night from May 25 to May 26
CA $173
CA $199 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (2,143 reviews)
We weren’t happy that parking was $24 a day and that the only part of the breakfast that was free was the coffee. Otherwise, everything else was fine.

Reviewed on May 12, 2026

New Haven Hotel
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from May 25 to May 26
CA $154
CA $177 total
May 25 - May 26
includes taxes & fees
7.4/10 Good! (1,297 reviews)
No breakfast noticed during check out.

Reviewed on May 12, 2026

The Capitol Hotel
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
The price is CA $142 per night from May 25 to May 26
CA $142
CA $163 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (1,297 reviews)
Comfortable beds

Reviewed on May 12, 2026

Holiday Inn Express Southington by IHG
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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.