Middlefield Vacations from $401

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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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $546, price is now $401 per person
$401
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
8/10 Very Good! (1,000 reviews)
Convenient, very outdated

Reviewed on Jun 22, 2026

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $577, price is now $435 per person
$435
per person
Aug 7 - Aug 10
found 7 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
9.2/10 Wonderful! (2,194 reviews)
Excellent staff & great location - close to many different restaurants & the hospital. Also the hotel has a parking garage across the street which is wonderful

Reviewed on Jun 28, 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 $791, price is now $611 per person
$611
per person
Aug 7 - Aug 10
found 7 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
2/10 (1 review)
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $982, price is now $767 per person
$767
per person
Aug 7 - Aug 10
found 7 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
9.2/10 Wonderful! (31 reviews)
Great stay with many amenities to enjoy within the building!

Reviewed on Apr 3, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $579, price is now $462 per person
$462
per person
Aug 7 - Aug 10
found 7 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
9.2/10 Wonderful! (995 reviews)
Beautiful, old building. Every thing was great from the room to the staff to breakfast. Cofee was awesome.

Reviewed on Jun 26, 2026

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Stay near popular Middlefield attractions

Lyman Orchards

8.4/5 (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
$127 nightly
The price is $146 total per night from Jul 6 to Jul 7
$146 total
Jul 6 - Jul 7
Total with taxes and fees
9.2/10 Wonderful! (2,206 reviews)
"For me, the highlight was the check-in staff and evening desk staff on June 28. They were upbeat, enthusiastic, engaging in a way that made me feel good being in this hotel. For the other two days of my stay the staff was fine, but did not equal the energy and personality of that first day. The room ..."

Reviewed on Jun 29, 2026

New Haven Hotel
Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

2 out of 5
1341 Silas Deane Hwy Wethersfield CT
Fully refundableReserve now, pay when you stay
$66 nightly
The price is $76 total per night from Jul 7 to Jul 8
$76 total
Jul 7 - Jul 8
Total with taxes and fees
7/10 Good! (1,201 reviews)
"This property was worn, but clean and quiet. There was some wear and tear in the bathroom, but nothing outrageous. Definitely a good cheap place to stay. There is a Mobil station and Red Lobster directly across the road, and plenty of shops of all kinds on the main road to either side of the motel. ..."

Reviewed on Jun 29, 2026

Motel 6 Wethersfield, CT - Hartford
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
$142 nightly
The price is $163 total per night from Jul 23 to Jul 24
$163 total
Jul 23 - Jul 24
Total with taxes and fees
8.6/10 Excellent! (1,038 reviews)
"Clean rooms, small. Outside of building looks horrible but inside everything is fine. Reasonable selection at the breakfast buffet ( although slimmer than in years past)."

Reviewed on Jun 28, 2026

Omni New Haven Hotel at Yale
See all 1,197 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 $401 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.