Middlefield Vacation Packages
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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.
Top Middlefield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Cheshire Welcome Inn
CA $1,208
per person
Oct 30 - Nov 5
found 4 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to New Haven (HVN)
8.4/10 Very good! (864 reviews)
The cleanliness of the room did not feel very reassuring. The sound insulation was extremely poor, and there was constant traffic on the road directly in front of the property, which made the room very noisy and difficult to sleep in. The air conditioner was also quite old and loud, adding even more noise during the night. Overall, the stay was much less comfortable than expected.
Reviewed on Aug 29, 2026
New Haven Hotel
Downtown New Haven
CA $888
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (2,262 reviews)
Very spacious room. Tired and a bit musty but clean and well-maintained. Lots of room to spread out; bathroom more than adequate. I really appreciated the enclosed, secure garage so close with the use of the footbridge. I do wish I'd been told I needed my room key to get out of the garage - I'd already turned it in. If it wasn't for the parking attendant letting me out, I'd have been stuck running across the street to get my key back from the front desk, all while blocking the exit.
Reviewed on Aug 30, 2026
Ready to book your vacation to Middlefield?
Middlefield Hotel Deals
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
CA $141
CA $162 total
Aug 31 - Sep 1
includes taxes & fees
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
CA $89
CA $104 total
Sep 3 - Sep 4
includes taxes & fees
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
CA $166
CA $191 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (2,290 reviews)
"Very spacious room. Tired and a bit musty but clean and well-maintained. Lots of room to spread out; bathroom more than adequate. I really appreciated the enclosed, secure garage so close with the use of the footbridge. I do wish I'd been told I needed my room key to get out of the garage - I'd already ..."
Reviewed on Aug 30, 2026
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.
Stay near popular Middlefield attractions
Lyman Orchards
8.4/10 (5 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.
Lake Beseck Beach
Why not spend a lazy afternoon at Lake Beseck Beach during your trip to Middlefield? Discover the area's waterfalls and mountain views.
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 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
Enjoy a round of golf in Middlefield at Indian Springs Golf Club. Take in the entertainment venues while you're in the area.
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.
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.
Powder Hill Dinosaur Park
Explore the great outdoors at Powder Hill Dinosaur Park, a lovely green space in Middlefield. Discover the area's waterfalls and mountain views.
Frequently asked questions
How much does a Middlefield vacation package cost?
Offering great value package deals from CA $658 on Expedia, you'll be pleasantly surprised at how much a vacation to Middlefield costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Middlefield?
Plan your trip for the low or shoulder season and you're likely to score cheap Middlefield vacation packages. Keep in mind that public holidays and major local events can impact prices, so do your research before booking.
How many days is enough for Middlefield?
Middlefield vacations come in various shapes and sizes, but to really get a feel for this place, we'd suggest 4 days is a good ballpark. In this timeframe, you can visit top attractions like Silver Lake State Access Area and Connecticut River State Wildlife Area and track down some hidden gems. Don't forget to visit neighbourhoods such as Washington Street Historic District and Main Street Historic District either. If you're clever with your time, you can even schedule a day trip outside of Middlefield too.
Is it worth booking a vacation package to Middlefield?
Popular for its skiing, nature and family-friendly attractions, a Middlefield vacation is a hit with all kinds of visitors. Be sure to visit leading sights like Lake Beseck Beach and Black Pond State Wildlife Area, and consider renting some wheels for day trips to experience even more.
How to find the best Middlefield package deals?
Use Expedia's filters to find some fabulous Middlefield package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Middlefield package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Middlefield vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights separately. Better still, you can customize your Middlefield escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Middlefield?
If you're planning an impromptu Middlefield getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Middlefield?
- Choose when to get away: Check your diary and get packing. Your preferred season and the available activities will also help you decide when to vacation in Middlefield.
- Plan your budget wisely: As well as the price of your hotel, you'll need to consider other expenses too. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Middlefield.
- Decide how many days away: Start by listing all the activities and sights you'd like to experience in Middlefield. Then, estimate how long you'll need for each, including any travel time.
- Combine your accommodations and airfare: After you've settled on your dates and duration, book the perfect Middlefield vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
