Middlefield Vacations from $430

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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 $589, price is now $430 per person
$430
per person
Aug 6 - Aug 9
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
Comfortable for a nights stay. Close to nice restaurants and shopping.

Reviewed on May 21, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $3,074, price is now $1,859 per person
$1,859
per person
Jul 7 - Jul 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
No reviews
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $947, price is now $758 per person
$758
per person
Jun 25 - Jun 28
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $792, price is now $643 per person
$643
per person
Jun 25 - Jun 28
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.6/10 Excellent! (1,019 reviews)
Front desk reception team is amazing. Breakfast was excellent and the server remembered my preferences from my last stay.

Reviewed on May 20, 2026

Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
Price was $834, price is now $679 per person
$679
per person
Jun 25 - Jun 28
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.6/10 Excellent! (1,006 reviews)
I only wish I could have stayed longer. I was injured shortly before my stay, and everything about Hilton Garden Inn was a balm. For the first time, I enjoyed their sizeable pool, which really calmed me. The staff is attentive and caring. The TV is large and boasts many channels. The mirrors are a good size and the chair and desk quite helpful. I slept like a queen. I hope to get this room again because it had a tub.

Reviewed on May 24, 2026

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Discover the most popular places to visit in Middlefield

Lyman Orchards

Lyman Orchards

4/5(4 reviews)

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
$122 nightly
The price is $140 total per night from May 26 to May 27
$140 total
May 26 - May 27
Total with taxes and fees
9.2/10 Wonderful! (2,138 reviews)
"The complimentary coffee was much appreciated. The staff were so great and helpful, and genuinely want your stay to be as perfect as possible. One thing that was repeatedly bothersome, even at 7:00 a.m., was the overly loud music in the back of the lobby area, and it was not calming music, it was ..."

Reviewed on May 22, 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
$92 nightly
The price is $105 total per night from May 25 to May 26
$105 total
May 25 - May 26
Total with taxes and fees
7.4/10 Good! (1,326 reviews)
"Bathroom door is broken. One roll of toilet paper and the other place to put toilet paper is broken and missing. There was no facial tissues at all. Bathroom need serious repairs in corners and was dingy."

Reviewed on May 24, 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 refundableReserve now, pay when you stay
$111 nightly
The price is $128 total per night from May 28 to May 29
$128 total
May 28 - May 29
Total with taxes and fees
8.8/10 Excellent! (1,310 reviews)
"Clean room, bathroom and bedding! Good breakfast! But the walls and doors were very noisy, it was annoying, so it wasn't soundproof. Overall, the location and atmosphere of the hotel were nice."

Reviewed on May 23, 2026

Holiday Inn Express Southington by IHG
See all 1,213 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 $430 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.