Middlefield Vacations from $277

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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.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $363, price is now $277 per person
$277
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.2/10 Very Good! (1,008 reviews)
Nice size room and very clean. Great price!

Reviewed on Oct 13, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $1,639, price is now $954 per person
$954
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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 $487, price is now $367 per person
$367
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (877 reviews)
Loud tv in adjoining room, went on late, but i covered my head with a pillow

Reviewed on Oct 11, 2025

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $3,646, price is now $2,752 per person
$2,752
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (53 reviews)
Incredible place - will definitely return.

Reviewed on Aug 19, 2024

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $567, price is now $434 per person
$434
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
Bartenders and front desk staff were very friendly!

Reviewed on Oct 15, 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

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 19 to Oct 20
$118 total
Oct 19 - Oct 20
Total with taxes and fees
7.4/10 Good! (1,022 reviews)
"Room was clean and comfortable. Staff were amazing"

Reviewed on Oct 12, 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
$99 nightly
The price is $114 total per night from Oct 26 to Oct 27
$114 total
Oct 26 - Oct 27
Total with taxes and fees
7.6/10 Good! (1,019 reviews)
"Great"

Reviewed on Oct 12, 2025

Best Western Hartford Hotel & Suites
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $192 total per night from Oct 29 to Oct 30
$192 total
Oct 29 - Oct 30
Total with taxes and fees
8.4/10 Very Good! (1,011 reviews)
"Friendly staff, very clean and the bed was great. We had the king deluxe room. I’ve never stayed in a big fancy hotel like that before so it was a little overwhelming but I got through it. Would stay there again if I ever came back to the area."

Reviewed on Oct 11, 2025

Omni New Haven Hotel at Yale
See all 1,070 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.

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 $277 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.