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.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
CA $765
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very good! (1,009 reviews)
It was a clean area , walking distance to lots of restaurants and my dog walks were very relaxing morning and late afternoon… I would recommend 100% and will return..
Thank you ..
Reviewed on Aug 12, 2026
Hyatus Luxury Residences City Crossing
The Hill
CA $2,389
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
9.4/10 Exceptional! (33 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
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
CA $2,378
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
9.6/10 Exceptional! (85 reviews)
I had an amazing stay at the Hyatus. The property was exceptionally clean and well maintained, which made me feel comfortable from the moment I arrived.
The location was perfect—convenient to everything I needed while still being quiet and peaceful, making it easy to relax after a busy week. Overall, it was a wonderful experience, and I would absolutely stay here again. Highly recommend!
Reviewed on Jul 6, 2026
Ready to book your vacation to Middlefield?
Middlefield Hotel Deals
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
CA $88
CA $103 total
Sep 3 - Sep 4
includes taxes & fees
7.2/10 Good! (1,027 reviews)
"My stay was ok will stay there again cheapest around and they are very helpful"
Reviewed on Aug 11, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
CA $128
CA $147 total
Aug 16 - Aug 17
includes taxes & 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
CA $198
CA $227 total
Sep 2 - Sep 3
includes taxes & fees
8.6/10 Excellent! (1,083 reviews)
"Some of the staff in the front office and f&b. Eugene at the door and Trisha at the desk ate amazing. Theirs another name in the restaurant, It'll come to me on my next review."
Reviewed on Aug 12, 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.
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 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.
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.
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.
Frequently asked questions
How much does a Middlefield vacation package cost?
Offering great value package deals from CA $765 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.
