Middlefield Vacations from $257

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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
Price was $344, price is now $257 per person
$257
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (1,070 reviews)
Beds comfortable. Breakfast selection good.

Reviewed on Aug 19, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $1,352, price is now $962 per person
$962
per person
Oct 24 - Oct 27
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
9.4/10 Exceptional! (312 reviews)
The hotel is beautiful and the grounds are wonderful. The staff was top notch. We will definitely stay again.

Reviewed on Aug 18, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $563, price is now $447 per person
$447
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,007 reviews)
It would’ve been better that you had posted that the pool was closed since 2020. My Wife wasn’t too happy about that.

Reviewed on Aug 18, 2025

Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
Price was $603, price is now $479 per person
$479
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (429 reviews)
Everything was good

Reviewed on Jul 25, 2025

Comfort Inn Naugatuck-Shelton, CT

Comfort Inn Naugatuck-Shelton, CT

2.5 out of 5
Price was $456, price is now $376 per person
$376
per person
Oct 24 - Oct 27
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
7.8/10 Good! (697 reviews)
The staff was friendly and the room was bigger then I thought it would be. Had a nice stay. No complaints.

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

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
$84 nightly
The price is $97 total per night from Aug 25 to Aug 26
$97 total
Aug 25 - Aug 26
Total with taxes and fees
7.6/10 Good! (1,007 reviews)
"We needed a place to rest our head for the night"

Reviewed on Aug 21, 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
$143 nightly
The price is $165 total per night from Sep 21 to Sep 22
$165 total
Sep 21 - Sep 22
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
"Convenience"

Reviewed on Aug 20, 2025

Omni New Haven Hotel at Yale
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
$125 nightly
The price is $144 total per night from Sep 1 to Sep 2
$144 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (864 reviews)
"Like the hotel i will stay there again"

Reviewed on Aug 20, 2025

Cambria Hotel New Haven University Area
See all 1,074 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 $257 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.