Middlefield Vacations from $570
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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.
Head of Pond House
$570
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to New Haven (HVN)
10/10 Exceptional! (13 reviews)
The cottage is quaint and old, it is showing its age. The beds were ever comfortable. The entertainment option was not a TV but a projector with a shoddy speaker. The spiral staircase to the upper level was treacherous to come down and several of the vertical supports were look making the decent and ascent scary. The pond side location was very nice and the little patio was special apart from the chainsaws from the unfortunately scheduled tree cutting by neighbors.
Reviewed on Sep 23, 2026
Landing Apartments New Haven Near Dixwell
Newhallville
$931
per person
Dec 17 - Dec 23
found 18 hours ago
Roundtrip flight included
Orlando (MCO) 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
Landing Furnished Apartment Near Yale University
Downtown New Haven
$810
per person
Dec 17 - Dec 23
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
2/10 (1 review)
Check in automated, but the key box was broken and it took me 30 on the phone with IT to get the keys. When I entered the apartment a water leak in the city had destroyed a chunk of the ceiling and there was a mess of drywall and dirty water on the floor. The firm tried to relocate me an hour away before promising to clean up and repair the problem while I was out, but maintenance never arrived. We had to book a hotel nearby. These people are incompetent
Reviewed on Sep 14, 2026
Hyatus Luxury Residences City Crossing
The Hill
$1,037
per person
Dec 17 - Dec 23
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (34 reviews)
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.
Reviewed on Aug 10, 2026
Don't see what you're looking for?
See all available trips from Columbus to Middlefield
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.
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.
Powder Hill Dinosaur Park
Walk among 200-million-year-old dinosaur footprints preserved in sandstone at Powder Hill Dinosaur Park. This free, open-air site offers a tangible connection to Connecticut's prehistoric past.
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 Sunflower Maze
Enjoy an outing to Lyman Orchards Sunflower Maze during your stay 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.
Middlefield Hotel Deals
The Capitol Hotel
440 Asylum St Hartford CT
$101 nightly
$116 total
Sep 30 - Oct 1
Total with taxes and fees
7.4/10 Good! (1,553 reviews)
"Easy check in and check out, clean room, nice views"
Reviewed on Sep 28, 2026
New Haven Hotel
229 George Street New Haven CT
$135 nightly
$155 total
Oct 27 - Oct 28
Total with taxes and fees
9.2/10 Wonderful! (2,359 reviews)
"Pleasant staff, nice facility"
Reviewed on Sep 29, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
$92 nightly
$106 total
Oct 4 - Oct 5
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 $570 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.
