Middlefield Vacations from $638

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $806, price is now $638 per person
$638
per person
Jun 26 - Jun 29
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (2,139 reviews)
Room was very clean. The only problem we had was that there were only 3 towels in the bathroom when the room was booked for four persons. Parking was great!

Reviewed on May 18, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,946, price is now $1,171 per person
$1,171
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
No reviews
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 $959, price is now $650 per person
$650
per person
Aug 1 - Aug 8
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
8/10 Very Good! (1,004 reviews)
We have been coming here for years and it is the best it’s ever been! Staff is friendly and accommodating. The rooms have been renovated and clean.

Reviewed on May 17, 2026

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $3,257, price is now $2,353 per person
$2,353
per person
Aug 1 - Aug 8
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
9.4/10 Exceptional! (369 reviews)
Exceptionally clean and wonderful staff

Reviewed on May 10, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $881, price is now $697 per person
$697
per person
Jun 26 - Jun 29
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Middlefield
View all trips

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
$115 nightly
The price is $132 total per night from May 24 to May 25
$132 total
May 24 - May 25
Total with taxes and fees
9.2/10 Wonderful! (2,139 reviews)
"Ver nice oroperty"

Reviewed on May 19, 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
$104 nightly
The price is $120 total per night from May 26 to May 27
$120 total
May 26 - May 27
Total with taxes and fees
7.4/10 Good! (1,309 reviews)
"The only positive of this place would be the view of the capitol building. The building and rooms are out-dated, but the worst part was the maintenance. The hotel has a lot of issues with hotel card readers on the room doors, which do not work or reset after a day. I had to get a new room the first ..."

Reviewed on May 19, 2026

The Capitol Hotel
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
$142 nightly
The price is $163 total per night from Jun 14 to Jun 15
$163 total
Jun 14 - Jun 15
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
"Frequent traveler here. This is not a 4-star hotel. During my stay, housekeeping took my newly purchased mascara ($40+) and one of my organic face towels. I spoke with several people, but no one followed up and no compensation was offered. Disappointing experience."

Reviewed on May 17, 2026

Omni New Haven Hotel at Yale
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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.