Middlefield Vacations from $407

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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 $609, price is now $407 per person
$407
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to New Haven (HVN)
9/10 Wonderful! (1,874 reviews)
The room was amazing the staff was great very helpful especially the desk attendant. Would stay here again.

Reviewed on Nov 28, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,729, price is now $1,072 per person
$1,072
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to New Haven (HVN)
No reviews
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $592, price is now $409 per person
$409
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
Absolutely loved this place. The lobby and room were great. I would stay at this location and with this chain again.

Reviewed on Nov 28, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $674, price is now $485 per person
$485
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Nice throwback hotel. Room was spotless, much old school charm. Check in was a little bumpy, otherwise a good stay.

Reviewed on Nov 17, 2025

The Blake Hotel

The Blake Hotel

4 out of 5
Downtown New Haven
Price was $684, price is now $504 per person
$504
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to New Haven (HVN)
9.4/10 Exceptional! (1,000 reviews)
Great ambiance, cozy decoration. Clean and comfortable rooms, love the kitchen, the bathroom on the room. Very spacious. Very friendly staff. Valet parking very convenient.

Reviewed on Nov 21, 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

Black Pond State Wildlife Area

Explore the great outdoors at Black Pond State Wildlife Area, a lovely green space in Middlefield. Take in the entertainment venues in this family-friendly area.

Black Pond State Wildlife Area

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
$89 nightly
The price is $102 total per night from Dec 14 to Dec 15
$102 total
Dec 14 - Dec 15
Total with taxes and fees
7.4/10 Good! (1,099 reviews)
This property has changed hands over the years. The management now is the best ever. The condition is good.

Reviewed on Nov 26, 2025

The Capitol Hotel
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $85 total per night from Dec 25 to Dec 26
$85 total
Dec 25 - Dec 26
Total with taxes and fees
9/10 Wonderful! (1,894 reviews)
Great location to restaurants and bars, room was clean, easy access to parking for fee

Reviewed on Nov 24, 2025

New Haven Hotel
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Fully refundable
$74 nightly
The price is $85 total per night from Dec 7 to Dec 8
$85 total
Dec 7 - Dec 8
Total with taxes and fees
7/10 Good! (1,008 reviews)
Stay here because it’s clean and the price is right for the money you can’t beat it plus you have excellent food at Capones restaurant 100 feet away for your convenience

Reviewed on Nov 25, 2025

Motel 6 New Haven - Branford, CT
See all 1,110 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 $407 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.