Middlefield Vacations from $462

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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.
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
Price was $479, price is now $462 per person
$462
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.2/10 Very Good! (642 reviews)
Great room with comfortable beds.

Reviewed on Nov 5, 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 $941, price is now $817 per person
$817
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (1,018 reviews)
Clean rooms, a bit outdated and showing signs of wear. Sunrise was gorgeous from my balcony. Food and drinks at the restaurant are quality. Staff was incredibly friendly and helpful, especially Chris at the front desk. I would stay here again.

Reviewed on Nov 7, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $602, price is now $547 per person
$547
per person
Jan 2 - Jan 4
found 11 hours ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
9.2/10 Wonderful! (889 reviews)
Very happy with my stay here! The staff was super friendly, the coffee shop on property had the most deeeelicious latte that I had throughout my entire trip! Love how the whole property is decorated as well. Very charming!

Reviewed on Nov 6, 2025

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

2.5 out of 5
Price was $870, price is now $799 per person
$799
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
9/10 Wonderful! (1,059 reviews)
Room was clean, quiet.

Reviewed on Nov 7, 2025

HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
Price was $574, price is now $561 per person
$561
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
9/10 Wonderful! (1,008 reviews)
Easy check-in, everyone at the desk was very friendly and helpful. The room was clean and comfortable.

Reviewed on Nov 2, 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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
$83 nightly
The price is $95 total per night from Nov 16 to Nov 17
$95 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (1,144 reviews)
The staff was very nice and professional. The room though, toilet seat was loose, door stopper was hanging off the wall, and the mattresses were EXTREMELY soft. The breakfast was very good though.

Reviewed on Nov 3, 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
$89 nightly
The price is $102 total per night from Nov 16 to Nov 17
$102 total
Nov 16 - Nov 17
Total with taxes and fees
7.4/10 Good! (1,075 reviews)
Yes

Reviewed on Nov 3, 2025

The Capitol Hotel
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd, Hartford, CT
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $104 total per night from Nov 30 to Dec 1
$104 total
Nov 30 - Dec 1
Total with taxes and fees
7.6/10 Good! (1,000 reviews)
Great staff, very clean room

Reviewed on Oct 29, 2025

Best Western Hartford Hotel & Suites
See all 1,068 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 $462 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.