Middlefield Vacations from $260

Book a Hotel + Flight or Car together to unlock savings

Photo by Chris Kailher

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.
Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
Price was $307, price is now $260 per person
$260
per person
Nov 14 - Nov 16
found 24 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (432 reviews)
The rooms were clean and the area was nice as well. Would stay again.

Reviewed on Sep 1, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,915, price is now $1,809 per person
$1,809
per person
Nov 28 - Dec 3
found 23 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to New Haven (HVN)
No reviews
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $832, price is now $633 per person
$633
per person
Nov 24 - Nov 30
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (1,014 reviews)
Clean room, and friendly service - Good breakfast offered. Nice overall!

Reviewed on Sep 15, 2025

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
Price was $511, price is now $433 per person
$433
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
9/10 Wonderful! (1,009 reviews)
It was extremely convenient since the car rentals are closed when we get in. Shuttle to the hotel, and back the next day to the airport for car rental. Very easy. Good breakfast too.

Reviewed on Sep 16, 2025

Simsbury Inn

Simsbury Inn

3.5 out of 5
Simsbury Center
Price was $1,294, price is now $1,123 per person
$1,123
per person
Nov 24 - Nov 30
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
9.2/10 Wonderful! (267 reviews)
The staff was super friendly. Our room was large and immaculate. The free breakfast had more items than I usually eat going out for breakfast (not and cold items). The pool and whirlpool were awesome, had great music playing and no one was there. Will definitely go back.

Reviewed on Sep 5, 2025

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 is lovely any time of year, but especially in spring when the apples and peaches are in bloom. These are their peach trees. Plus, Lyman orchard's store has great cider, sandwiches, and snacks.

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
$148 nightly
The price is $170 total per night from Sep 28 to Sep 29
$170 total
Sep 28 - Sep 29
Total with taxes and fees
8.8/10 Excellent! (1,766 reviews)
"Hotel was nice. Service was good"

Reviewed on Sep 15, 2025

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 $106 total per night from Sep 21 to Sep 22
$106 total
Sep 21 - Sep 22
Total with taxes and fees
7.4/10 Good! (1,033 reviews)
Overnight stay
"The staff is very polite and helpful. Breakfast was very good. I would recommend"

Reviewed on Sep 14, 2025

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
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $183 total per night from Oct 5 to Oct 6
$183 total
Oct 5 - Oct 6
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
"Great location for a parent of Yale student. Front desk staff were not very welcoming or friendly whenever questions were asked of them about the hotel and area. I felt like an inconvenience - same with room Service staff. Door gentlemen were all lovely as were the cleaning staff."

Reviewed on Sep 13, 2025

Omni New Haven Hotel at Yale
See all 1,081 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.

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 $260 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

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.