Middlefield Vacations from $603
Book a Hotel + Flight or Car together to unlock savings
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.
The Scranton Seahorse Inn
Madison Center
$603
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9/10 Wonderful! (245 reviews)
Excellent B&B. Great breakfast. Lovely area. Walk around to local stores and restaurants. And beach is nearby.
Reviewed on Aug 1, 2026
Landing Furnished Apartment Near Yale University
Downtown New Haven
$625
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
2/10 (1 review)
Was unable to enter the unit as the key was not available in the Lockbox. Landing (the rental company) was unable to locate the key, which was apparently with the cleaning staff, who were unavailable. We ended up having to rent another property for our visit.
Reviewed on Jun 2, 2026
Landing Apartments New Haven Near Dixwell
Newhallville
$876
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.
Reviewed on May 25, 2026
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View all tripsStay near popular Middlefield attractions
Lyman Orchards
8.4/10 (5 reviews)
This 12th-generation family farm offers seasonal fruit picking and country charm since 1741. Wander through apple orchards, navigate corn mazes, or savor fresh-baked pies at the historic Apple Barrel market.
Lake Beseck Beach
This exclusive lakeside retreat offers Middlefield residents a peaceful swimming spot with clear waters. Reserve the beach pavilion for private gatherings while enjoying scenic views of Lake Beseck.
Beseck Lake
Commune with nature and explore the great outdoors at Beseck Lake during your travels in Middlefield. Discover the area's waterfalls and mountain views.
Indian Springs Golf Club
This scenic 9-hole course challenges players with blind shots and elevation changes across immaculate fairways. Enjoy a post-round meal at the Fairweather Cafe while overlooking the meticulously maintained grounds.
Lyman Meadow Golf Club
Two championship courses by legends Robert Trent Jones Sr. and Gary Player grace Connecticut's rolling hills. Enjoy strategic play on meticulously maintained fairways before unwinding at the on-site 1741 Pub & Grill.
Black Pond State Wildlife Area
This tranquil wildlife area features a picturesque pond and scenic Mattabesett Trail with stunning overlooks. Explore by kayak from the boat launch or hike to the ridge for breathtaking sunset views.
Lyman Orchards Corn Maze
Enjoy an outing to Lyman Orchards Corn Maze during your stay in Middlefield. Discover the area's waterfalls and mountain views.
Lyman Orchards Sunflower Maze
Enjoy an outing to Lyman Orchards Sunflower Maze during your stay in Middlefield. Discover the area's waterfalls and mountain views.
Middlefield Hotel Deals
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
$72 nightly
$83 total
Sep 1 - Sep 2
Total with taxes and fees
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
$95 nightly
$109 total
Sep 7 - Sep 8
Total with taxes and fees
8.6/10 Excellent! (1,416 reviews)
"It was ok a little dated breakfast was pretty good coffee was excellent ..."
Reviewed on Aug 11, 2026
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
Fully refundableReserve now, pay when you stay
$142 nightly
$163 total
Sep 2 - Sep 3
Total with taxes and fees
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 $603 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.