Middlefield Vacations from $334

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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.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,052 reviews)
It was walking distance to Thompson’s point where the music festival I went to see was being held. The staff from the front desk to cleaning staff, were all very friendly. More hooks and/or towel bars in the bathroom. Other than the shelf/rack that all the towels were stored on that is IN THE SHOWER (i.e. not practical to keep your towels on while you’re staying for a few days) there was 1 hook with 2 prongs on the door. It was a pain enough for me, and I stayed in the room by myself. I can’t imagine how aggravating it would be for a couple or a family.

Reviewed on Aug 15, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
It use to be clean and quiet. Carpets are stained. Mattresses too soft. They book Art all teams so kids are running up and down the halls unsupervised. Plus- the families take over the lobby and outdoor space. It’s a zoo and trash barrels overflowing. They should post tournament weeks so others stay away.

Reviewed on Aug 15, 2025

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to New Haven (HVN)
8.4/10 Very Good! (1,004 reviews)
Very clean and quiet. Wonderful staff.

Reviewed on Aug 14, 2025

Clarion Inn

Clarion Inn

3 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to New Haven (HVN)
7.6/10 Good! (1,009 reviews)
Bed was super comfy!!

Reviewed on Aug 1, 2025

Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (423 reviews)
Everything was good

Reviewed on Jul 25, 2025

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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

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

The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $96 total per night from Aug 28 to Aug 29
$96 total
Aug 28 - Aug 29
Total includes taxes and fees
7.4/10 Good! (1,019 reviews)
"We lucked into finding this place with 4th of July Fireworks all around this was the perfect location."

Reviewed on Aug 12, 2025

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
$111 nightly
The price is $128 total per night from Aug 31 to Sep 1
$128 total
Aug 31 - Sep 1
Total includes taxes and fees
8.6/10 Excellent! (1,064 reviews)
"The convenience of the shopping mall with restaurants. There was plenty of parking without having to walk much to far from the hotel."

Reviewed on Aug 11, 2025

Holiday Inn Express Southington by IHG
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $136 total per night from Sep 1 to Sep 2
$136 total
Sep 1 - Sep 2
Total includes taxes and fees
8.6/10 Excellent! (852 reviews)
"The hotel staff, room and facilities was great. The breakfast service was VERY SLOW! Almost walked away without waiting. Would recommend visitors go out to eat instead."

Reviewed on Aug 14, 2025

Cambria Hotel New Haven University Area
See all 1,066 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.

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Frequently asked questions

How much does a Middlefield vacation package cost?
Offering great value package deals from $334 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.