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.
Liberty Inn

Liberty Inn

2 out of 5
Price was CA $792, price is now CA $763 per person
CA $763
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7.6/10 Good! (657 reviews)
I stayed here with my girlfriend over the July fourth weekend. It was inexpensive. Enjoyable. And the staff was super friendly. The television hadthebtelemundk channel which was awesome because it aired the word cup soccer games. The staff was excellent. Front desk help was superb.

Reviewed on Jul 10, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $4,279, price is now CA $3,302 per person
CA $3,302
per person
Aug 22 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to New Haven (HVN)
No reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Westbrook Center
Price was CA $1,588, price is now CA $1,575 per person
CA $1,575
per person
Aug 16 - Aug 20
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.8/10 Excellent! (1,000 reviews)
Very nice place would stay again.

Reviewed on Jul 14, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $1,027, price is now CA $910 per person
CA $910
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very good! (1,001 reviews)
Still the same wonderful little place as the last time I stayed here!

Reviewed on Jul 11, 2026

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Middlefield Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Jul 26 to Jul 27
CA $182
CA $209 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (2,231 reviews)
"The staff was nice but the room needs in improvement A.C was not working properly and the sheets and blankets needs to be changed."

Reviewed on Jul 14, 2026

New Haven Hotel
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
The price is CA $136 per night from Aug 9 to Aug 10
CA $136
CA $157 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (1,371 reviews)
"I rated this stay one star because myself and my teenage son were stuck in one of the two elevators for about 10 minutes. I called the hotel directly from inside the elevator and the operator/ front desk clerk proceeded to ask for my cell phone number, and that they will call me back. I did not think ..."

Reviewed on Jul 14, 2026

Holiday Inn Express Southington by IHG
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Jul 26 to Jul 27
CA $201
CA $232 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (1,059 reviews)
"Room was not ready after 4 pm. But hotel is nicely maintained"

Reviewed on Jul 12, 2026

Omni New Haven Hotel at Yale
See all 1,194 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.
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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.
See properties

Frequently asked questions

How much does a Middlefield vacation package cost?
Offering great value package deals from CA $763 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?

  1. 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.
  2. 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.
  3. 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.
  4. Combine your accommodations and airfare: After you've settled on your dates and duration, book the perfect Middlefield vacation package for you.

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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.