Middlefield Vacations from $638

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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.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $841, price is now $638 per person
$638
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,986, price is now $1,227 per person
$1,227
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,172, price is now $854 per person
$854
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $990, price is now $744 per person
$744
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.6/10 Exceptional! (73 reviews)
I had a great stay at this property overall. The room was clean, comfortable, and well-maintained, which made it easy to relax after a long day. The staff was friendly and helpful, always willing to answer questions and make sure everything was taken care of. The kitchen was stocked with the basics needed for cooking, which was convenient during the stay. Parking was also easy to access and felt safe, which was a big plus. The location was convenient, close to nearby attractions, restaurants, and stores. If I had to mention one thing for improvement, it would be minor updates to some areas to make the space feel a bit more modern. Overall, I would definitely recommend this property and would consider staying here again in the future.

Reviewed on May 5, 2026

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Discover the most popular places to visit in Middlefield

Lyman Orchards

Lyman Orchards

You can do some window-shopping at Lyman Orchards during your visit to Middlefield. Take in the entertainment venues while you're in the area.

Lyman Orchards

Indian Springs Golf Club

Enjoy a round of golf in Middlefield at Indian Springs Golf Club. Take in the entertainment venues while you're in the area.

Indian Springs Golf Club

Lyman Meadow Golf Club

Enjoy a round of golf in Middlefield at Lyman Meadow Golf Club. Take in the entertainment venues while you're in the area.

Lyman Meadow Golf Club

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
$132 nightly
The price is $152 total per night from Jun 7 to Jun 8
$152 total
Jun 7 - Jun 8
Total with taxes and fees
9.2/10 Wonderful! (2,143 reviews)
"Easy check in. Super clean hotel. Friendly staff."

Reviewed on May 25, 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
$89 nightly
The price is $103 total per night from May 28 to May 29
$103 total
May 28 - May 29
Total with taxes and fees
7.4/10 Good! (1,334 reviews)
"Perfect spot to stay in Hartford right in front of the capital"

Reviewed on May 26, 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
$121 nightly
The price is $139 total per night from May 31 to Jun 1
$139 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (1,313 reviews)
"The staff was welcoming and friendly. The property was very clean, my only problem(s) was the room smelled like smoke for a non smoking room. The other problem was the mold on the ceiling in the bathroom it’s not healthy. It was a good stay for what it was needed for a weekend stay to spend time ..."

Reviewed on May 26, 2026

Holiday Inn Express Southington by IHG
See all 1,194 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 $638 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.