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.
Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (2,473 reviews)
Very clean and very nice.

Reviewed on Aug. 2, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.8/10 Excellent! (1,047 reviews)
I see lot of bugs in the room

Reviewed on Aug. 2, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.8/10 Excellent! (827 reviews)
Very near Yale university. The hotel is very clean and the hotel staff were kind and helpful. I got a work out in their nice fitness room. I enjoyed my stay before making my self into NYC.

Reviewed on Aug. 2, 2025

Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.2/10 Very Good! (1,001 reviews)
Clean, professional

Reviewed on Jul. 21, 2025

Comfort Inn Naugatuck-Shelton, CT

Comfort Inn Naugatuck-Shelton, CT

2.5 out of 5
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
7.8/10 Good! (692 reviews)
The staff was friendly and the room was bigger then I thought it would be. Had a nice stay. No complaints.

Reviewed on Jul. 25, 2025

Ready to book your vacation to Middlefield?

 

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Middlefield Hotel Deals

The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Aug 24 to Aug 25
CA $105
CA $121 total
Aug 24 - Aug 25
includes taxes & fees
7.4/10 Good! (1,001 reviews)
"Each stuff member was very friendly"

Reviewed on Jul. 30, 2025

The Capitol Hotel
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Fully refundable
The price is CA $98 per night from Aug 12 to Aug 13
CA $98
CA $114 total
Aug 12 - Aug 13
includes taxes & fees
6.8/10 (1,003 reviews)
"Good place"

Reviewed on Jul. 29, 2025

Motel 6 New Haven - Branford, CT
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Aug 18 to Aug 19
CA $186
CA $214 total
Aug 18 - Aug 19
includes taxes & fees
8.6/10 Excellent! (827 reviews)
"The staff was very nice and accommodating. Parking on site was very easy and nice, though the cost seemed a little high. The hotel is walkable distance to a lot of the things we wanted to do / see and the restaurants we wanted to eat at."

Reviewed on Jul. 26, 2025

Cambria Hotel New Haven University Area
See all 1,063 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Middlefield vacation package cost?
Offering great value package deals from CA $539 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.