Middlefield Vacations from $572

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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.
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
per person
Aug 8 - Aug 11
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
8.8/10 Excellent! (1,697 reviews)
Clean. Shuttle bus offered on Fridays and Saturdays to Mohegan. Room was good. Breakfast in the morning was good.

Reviewed on Jun 29, 2025

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
per person
Sep 19 - Sep 22
found 8 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (16 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.

Reviewed on Jun 27, 2025

Mayflower Inn & Spa, Auberge Resorts Collection

Mayflower Inn & Spa, Auberge Resorts Collection

5 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (53 reviews)
Incredible place - will definitely return.

Reviewed on Aug 19, 2024

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
Save 100% on your flight
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
We have visited Saybrook Point Resort several times and it is consistent in providing an excellent customer experience.

Reviewed on Jun 29, 2025

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.6/10 Exceptional! (50 reviews)
It was a great place. Highly recommend!

Reviewed on Jun 11, 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 Jul 1 to Jul 2
$118 total
Jul 1 - Jul 2
Total includes taxes and fees
7.4/10 Good! (1,004 reviews)
"It's not luxurious BUT it is upgraded with modern conveniences and is CLEAN. I had a good night's rest on a comfortable bed and a nice hot shower. Parking is a little scary to navigate at first underground, but it was secure and I appreciate that because I returned back to my room after 2a.m."

Reviewed on Jun 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
$127 nightly
The price is $146 total per night from Jul 13 to Jul 14
$146 total
Jul 13 - Jul 14
Total includes taxes and fees
8.8/10 Excellent! (1,607 reviews)
"It was clean and kept up well"

Reviewed on Jun 28, 2025

New Haven Hotel
La Quinta Inn & Suites by Wyndham New Haven
La Quinta Inn & Suites by Wyndham New Haven
3 out of 5
400 Sargent Dr, New Haven, CT
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $113 total per night from Jul 6 to Jul 7
$113 total
Jul 6 - Jul 7
Total includes taxes and fees
5.8/10 (1,009 reviews)
"I like the hotel."

Reviewed on Jun 28, 2025

La Quinta Inn & Suites by Wyndham New Haven
See all 1,069 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 $572 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.