Middlefield Vacations from $239

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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.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Save 100% on your flight
Price was $344, price is now $239 per person
$239
per person
Dec 11 - Dec 14
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (1,164 reviews)
Noisy - mostly because of road but the facility itself was really nice and I loved the room itself

Reviewed on Oct 19, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $399, price is now $293 per person
$293
per person
Dec 11 - Dec 14
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (889 reviews)
The bar downstairs is so fun, and their pizza night provided us with the best pizza in New Haven (better than the famous spots we all know). The bartenders made our trip, and showed us the warmth of the people of New Haven. Do not skip the bar! Even if you do not drink, the games are great and the food is even better.

Reviewed on Oct 17, 2025

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $564, price is now $418 per person
$418
per person
Dec 11 - Dec 14
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (21 reviews)
The apartment was very clean, well maintained and beautiful decor. The golf simulator was much enjoyed by my son. It's close to the train station, but more of a 20 minute walk to the center of Yale. If you are looking for space and comfort, this is a great place, but just not as close to Yale as other options (though close to Yale medical school).

Reviewed on Sep 16, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $435, price is now $340 per person
$340
per person
Dec 11 - Dec 14
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,016 reviews)
Everything was great!

Reviewed on Oct 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 $708, price is now $563 per person
$563
per person
Dec 24 - Dec 29
found 5 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,018 reviews)
Access to airport and service for my early Lyft was great

Reviewed on Oct 17, 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

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Fully refundable
$70 nightly
The price is $81 total per night from Oct 26 to Oct 27
$81 total
Oct 26 - Oct 27
Total with taxes and fees
7/10 Good! (1,020 reviews)
"Easy to get to, clean and affordable. The pizza bar at the end of the property is huge plus. Could use a hair dryer or coffee in the room but considering the price still an excellent choice."

Reviewed on Oct 11, 2025

Motel 6 New Haven - Branford, CT
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
$98 nightly
The price is $113 total per night from Nov 16 to Nov 17
$113 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (1,139 reviews)
"The room was clean and staff was friendly. We enjoyed the queen beds."

Reviewed on Oct 19, 2025

Holiday Inn Express Southington by IHG
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $118 total per night from Oct 26 to Oct 27
$118 total
Oct 26 - Oct 27
Total with taxes and fees
7.4/10 Good! (1,042 reviews)
"Perfect for our stay convenient location"

Reviewed on Oct 18, 2025

The Capitol Hotel
See all 1,078 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 $239 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.