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.
Aderi Hotel Niantic

Aderi Hotel Niantic

2 out of 5
Price was CA $875, price is now CA $858 per person
CA $858
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
6.2/10 (673 reviews)
Front desk staff at check in was so polite and friendly!

Reviewed on Aug. 12, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was CA $2,382, price is now CA $1,863 per person
CA $1,863
per person
Oct 2 - Oct 5
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
No reviews
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
Price was CA $1,285, price is now CA $1,212 per person
CA $1,212
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
8.8/10 Excellent! (1,737 reviews)
Property was a little out dated.. you could see the damage in the hallway walls from the cleaners carts. I could hear the neighbor next room over enjoying herself. Overall it was a place to rest my head for the night and it served its purpose!

Reviewed on Aug. 27, 2025

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
Price was CA $1,343, price is now CA $1,304 per person
CA $1,304
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (2,537 reviews)
Very close to Moheagan Sun

Reviewed on Aug. 25, 2025

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

3 out of 5
Price was CA $1,335, price is now CA $1,335 per person
CA $1,335
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (1,006 reviews)
Breakfast was excellent. Pool could be a lot warmer. Multiple people came in to pool area, put feet in the water, tried to get into the water but then left a few minutes after not going in.

Reviewed on Aug. 23, 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 $117 per night from Aug 28 to Aug 29
CA $117
CA $134 total
Aug 28 - Aug 29
includes taxes & fees
7.6/10 Good! (1,009 reviews)
"It was good"

Reviewed on Aug. 24, 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 Sep 1 to Sep 2
CA $98
CA $115 total
Sep 1 - Sep 2
includes taxes & fees
6.8/10 (1,011 reviews)
"Great location, quiet & yet right near Rt 95. Clean, nice room, polite staff!!!"

Reviewed on Aug. 25, 2025

Motel 6 New Haven - Branford, CT
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 $198 per night from Sep 21 to Sep 22
CA $198
CA $228 total
Sep 21 - Sep 22
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Staff was amazing, from the lobby staff to the housekeeping and wonderful in room dining. Unfortunately I had a fall in front of the hotel, quite loud as I injured both knees and ankles, however no staff 😟came to assist me, despite having dropped all my packages and bloodied my knees. Please ask ..."

Reviewed on Aug. 23, 2025

Omni New Haven Hotel at Yale
See all 1,074 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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Frequently asked questions

How much does a Middlefield vacation package cost?
Offering great value package deals from CA $858 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.