Middlefield Vacations from $419

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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.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $502, price is now $419 per person
$419
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to New Haven (HVN)
9/10 Wonderful! (1,874 reviews)
They didn't have breakfast available

Reviewed on Jan 16, 2026

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 $658, price is now $510 per person
$510
per person
Mar 13 - Mar 16
found 24 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.4/10 Exceptional! (21 reviews)
Very quiet, clean and peaceful accommodation. Enjoyed our stay here. Very spacious apartment with everything you need for a comfortable stay. Felt right at home - away from home. Highly recommend.

Reviewed on Jan 7, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $624, price is now $487 per person
$487
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Older building with decent rooms, but definitely could use some more love

Reviewed on Jan 19, 2026

Landing Modern 2bd, Gym

3 out of 5
West New Haven
Price was $686, price is now $546 per person
$546
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to New Haven (HVN)
No reviews
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Westbrook Center
Save 100% on your flight
Price was $586, price is now $487 per person
$487
per person
Feb 27 - Mar 2
found 22 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
8.8/10 Excellent! (1,002 reviews)
It was perfect for an evening away, quiet, friendly staff, beautiful views, and great Sunday brunch

Reviewed on Dec 29, 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

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $108 total per night from Jan 27 to Jan 28
$108 total
Jan 27 - Jan 28
Total with taxes and fees
9/10 Wonderful! (2,004 reviews)
Staff was awesome.

Reviewed on Jan 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
$88 nightly
The price is $102 total per night from Jan 21 to Jan 22
$102 total
Jan 21 - Jan 22
Total with taxes and fees
7.4/10 Good! (1,142 reviews)
My son and I stayed here to be near the convention center which was a very convenient 6 minute drive. The hotel had a secure parking garage for just $15 per night which was great. The room had just enough space with all the amenities you need: microwave, fridge, hair dryer, iron, etc. There were ...

Reviewed on Jan 14, 2026

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
$86 nightly
The price is $99 total per night from Feb 7 to Feb 8
$99 total
Feb 7 - Feb 8
Total with taxes and fees
8.6/10 Excellent! (1,207 reviews)
The room was drafty around the heating unit. Additionally, this hotel, like most newly built hotels, uses an automatic thermostat for the heat and cool. When the thermostat is set and it gets a little too warm in the room, and you turn it down a couple degrees the AC kicks on rather than just allowing ...

Reviewed on Jan 14, 2026

Holiday Inn Express Southington by IHG
See all 1,149 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 $419 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.