Middlefield Vacations from $264

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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.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $320, price is now $264 per person
$264
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
Spotless, lovely room. Attentive staff.

Reviewed on Dec 26, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $1,732, price is now $952 per person
$952
per person
Feb 27 - Mar 2
found 10 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
No reviews
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $366, price is now $288 per person
$288
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Everything was amazing

Reviewed on Dec 14, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $404, price is now $319 per person
$319
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
Great stay overall. Wish it was easier to walk to good restaurants. Had to drive to good food.

Reviewed on Dec 27, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $641, price is now $507 per person
$507
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.4/10 Exceptional! (336 reviews)
beautiful room and views

Reviewed on Dec 13, 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

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

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $122 total per night from Jan 25 to Jan 26
$122 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
9/10 Wonderful! (1,967 reviews)
The staff at this hotel, including Stephanie at the front desk, could not have been nicer and more competent. They were incredibly helpful to my family. The hotel is also well situated to downtown and Yale university. We would stay here again.

Reviewed on Dec 30, 2025

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
$89 nightly
The price is $102 total per night from Jan 2 to Jan 3
$102 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
7.4/10 Good! (1,119 reviews)
Great location and a very clean and comfortable room. The staff was very helpful and went out of their way to help me.

Reviewed on Dec 17, 2025

The Capitol Hotel
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Fully refundable
$104 nightly
The price is $120 total per night from Jan 25 to Jan 26
$120 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
Great stay overall. Wish it was easier to walk to good restaurants. Had to drive to good food.

Reviewed on Dec 27, 2025

Cambria Hotel New Haven University Area
See all 1,148 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 $264 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.