Middlefield Vacations from $459

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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.

The Latest Middlefield vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was $582, price is now $459 per person
$459
per person
Oct 6 - Oct 12
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8/10 Very Good! (1,687 reviews)
Hotel was quiet. Staff was great. Parking is limited and congested due to big truck parking

Reviewed on Jul 14, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $1,760, price is now $1,206 per person
$1,206
per person
Oct 6 - Oct 12
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Las Flores Villa

Las Flores Villa

5 out of 5
Save 100% on your flight
Price was $850, price is now $584 per person
$584
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to New Haven (HVN)
10/10 Exceptional! (1 review)

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Save 100% on your flight
Price was $673, price is now $520 per person
$520
per person
Oct 6 - Oct 12
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) 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

Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

2.5 out of 5
Price was $851, price is now $660 per person
$660
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to New Haven (HVN)
8.4/10 Very Good! (1,003 reviews)
The staff was very friendly and the free breakfast was filled with different items. The hotel and property was very clean. The cleaning crew uses a very strong smelling carpet deodorizer which was also all over the countertops which I had to clean. It was obvious that they just throw it everywhere. The water pressure was more than lacking with a standard home shower head as well. Although there were 2 main complaints, for this price and location, this is a great place to book.

Reviewed on Jul 14, 2026

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Stay near popular Middlefield attractions

Lyman Orchards

8.4/10 (5 reviews)
This 12th-generation family farm offers seasonal fruit picking and country charm since 1741. Wander through apple orchards, navigate corn mazes, or savor fresh-baked pies at the historic Apple Barrel market.
See properties

Middlefield Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $155 total per night from Jul 26 to Jul 27
$155 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (2,231 reviews)
"The staff was nice but the room needs in improvement A.C was not working properly and the sheets and blankets needs to be changed."

Reviewed on Jul 14, 2026

New Haven 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
$97 nightly
The price is $112 total per night from Aug 9 to Aug 10
$112 total
Aug 9 - Aug 10
Total with taxes and fees
8.8/10 Excellent! (1,371 reviews)
"I rated this stay one star because myself and my teenage son were stuck in one of the two elevators for about 10 minutes. I called the hotel directly from inside the elevator and the operator/ front desk clerk proceeded to ask for my cell phone number, and that they will call me back. I did not think ..."

Reviewed on Jul 14, 2026

Holiday Inn Express Southington by IHG
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $162 total per night from Jul 26 to Jul 27
$162 total
Jul 26 - Jul 27
Total with taxes and fees
8.6/10 Excellent! (1,058 reviews)
"Room was not ready after 4 pm. But hotel is nicely maintained"

Reviewed on Jul 12, 2026

Omni New Haven Hotel at Yale
See all 1,193 properties in Middlefield
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.

Find the Best Middlefield Vacation Packages

Middlefield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Toyota Presents Oakdale Theatre, Brownstone Exploration & Discovery Park and Dinosaur State Park

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Frequently asked questions

How much does a Middlefield vacation package cost?
Offering great value package deals from $459 on Expedia, you'll be pleasantly surprised at how much a vacation to Middlefield costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Middlefield?
You're likely to find lower rates and better availability in December, January and February. Check out our cheap Middlefield vacation packages and you could land some excellent off-season deals.
How many days is enough for Middlefield?
To fully enjoy a Middlefield vacation, we recommend booking for 2 days. Divide your time between visiting Lyman Meadow Golf Club, Black Pond State Wildlife Area and other major sights, in addition to experiencing neighborhoods like Washington Street Historic District and Main Street Historic District. If you've got some spare time, include a day trip in your Middlefield vacation itinerary.
Is it worth booking a vacation package to Middlefield?
Whether you'd like to visit major sights such as Powder Ridge Mountain Park and Resort and Lake Beseck Beach on your Middlefield vacation, or coming for its great skiing, nature and family-friendly attractions, there's something for everyone here. With so many things to do, you'll soon learn why so many visitors think Middlefield is a good vacation destination.
How to find the best Middlefield package deals?
Use Expedia's filters to help you find some terrific Middlefield package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Middlefield package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Middlefield vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations individually. Better still, you can personalize your Middlefield escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Middlefield?
If you're considering a spur-of-the-moment Middlefield getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Middlefield vacation packages?
Your Middlefield getaway is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.