Middlefield Vacations from $475

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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.

The Latest Middlefield vacation packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $570, price is now $475 per person
$475
per person
Dec 18 - Dec 20
found 8 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
8/10 Very Good! (1,005 reviews)
Unfortunately, the shower did not have hot water. The TV was way too far from the bed and was very small - of no use; Minimal items....a bit pathetic. The room had a kitchen - which was not requested. The price was too high, given the poor appearance and lack of essential hot water at 7:00 a.m. in the morning!

Reviewed on Oct 29, 2026

Las Flores Villa

Las Flores Villa

5 out of 5
Save 100% on your flight
Price was $12,409, price is now $8,015 per person
$8,015
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
10/10 Exceptional! (1 review)

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $1,854, price is now $1,570 per person
$1,570
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $7,101, price is now $6,031 per person
$6,031
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
9.4/10 Exceptional! (66 reviews)

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $674, price is now $573 per person
$573
per person
Dec 18 - Dec 20
found 10 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
9.2/10 Wonderful! (35 reviews)
Bed had no mattress cover but was very comfortable. Only one working lamp. Vents could use a good cleaning. I would recommend it and would stay again.

Reviewed on Oct 25, 2026

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Stay near popular Middlefield attractions

Lyman Orchards

8.4/10 (5 reviews)
This 12th-generation family farm offers seasonal fruit picking and country charm since 1741. Wander through apple orchards, navigate corn mazes, or savor fresh-baked pies at the historic Apple Barrel market.
See properties

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
$108 nightly
The price is $124 total per night from Nov 28 to Nov 29
$124 total
Nov 28 - Nov 29
Total with taxes and fees
7.2/10 Good! (1,608 reviews)
"Horrible ex"

Reviewed on Oct 28, 2026

The Capitol Hotel
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $155 total per night from Nov 25 to Nov 26
$155 total
Nov 25 - Nov 26
Total with taxes and fees
New Haven Hotel
Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

2 out of 5
1341 Silas Deane Hwy Wethersfield CT
Fully refundable
$64 nightly
The price is $74 total per night from Nov 24 to Nov 25
$74 total
Nov 24 - Nov 25
Total with taxes and fees
7/10 Good! (1,371 reviews)
"Not the greatest at all. Bath towels were the size of a bath mat, ice bucket in room but no ice machine, Nothing good out at all, staff wasn’t all that friendly or helpful or suggesting of anything to anticipate our needs at all."

Reviewed on Oct 29, 2026

Motel 6 Wethersfield, CT - Hartford
See all 1,245 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.

Find the Best Middlefield Vacation Packages

Middlefield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Toyota Presents Oakdale Theatre, Brownstone Exploration & Discovery Park and Dinosaur State Park

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Frequently asked questions

How much does a Middlefield vacation package cost?
Offering great value package deals from $475 on Expedia, you'll be pleasantly surprised at how much a vacation to Middlefield costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Middlefield?
You're likely to find lower rates and better availability in December, January and February. Check out our cheap Middlefield vacation packages and you could land some excellent off-season deals.
How many days is enough for Middlefield?
To fully enjoy a Middlefield vacation, we recommend booking for 2 days. Divide your time between visiting Lyman Meadow Golf Club, Black Pond State Wildlife Area and other major sights, in addition to experiencing neighborhoods like Washington Street Historic District and Main Street Historic District. If you've got some spare time, include a day trip in your Middlefield vacation itinerary.
Is it worth booking a vacation package to Middlefield?
Whether you'd like to visit major sights such as Powder Ridge Mountain Park and Resort and Lake Beseck Beach on your Middlefield vacation, or coming for its great skiing, nature and family-friendly attractions, there's something for everyone here. With so many things to do, you'll soon learn why so many visitors think Middlefield is a good vacation destination.
How to find the best Middlefield package deals?
Use Expedia's filters to help you find some terrific Middlefield package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Middlefield package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Middlefield vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations individually. Better still, you can personalize your Middlefield escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Middlefield?
If you're considering a spur-of-the-moment Middlefield getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Middlefield vacation packages?
Your Middlefield getaway is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.