Middlefield Vacations from $499

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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.
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
Price was $601, price is now $499 per person
$499
per person
Jul 17 - Jul 20
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,012 reviews)
We were in town for a funeral. It was a quiet, clean place to stay. Close to everywhere we needed to be. We had a family group staying and it was nice to be able to catch up before and after scheduled activities. I would definitely stay here again.

Reviewed on Jun 12, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Save 100% on your flight
Price was $767, price is now $534 per person
$534
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8/10 Very Good! (1,006 reviews)
The place wasn't terrible and the staff was pleasant. The name and photos are misleading. This is basically a motel trying to seem like an inn or small hotel. It looks like the type of place that attracts a questionable clientele, but because it's Old Saybrook, they probably get a lot of wedding/event guests. The room itself was clean and pleasantly furnished, but the one easily accessible outlet was worn out and chargers kept falling out. The tub had a large crack in it (we did not use it). It was overall fine if you're staying for those reasons or a long distance travel break, but if you're looking for a couples weekend/nice place to stay, this isn't it.

Reviewed on Jun 13, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,086, price is now $1,680 per person
$1,680
per person
Jul 17 - Jul 20
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
No reviews
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $711, price is now $577 per person
$577
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
2/10 (1 review)
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Price was $1,430, price is now $1,188 per person
$1,188
per person
Aug 7 - Aug 10
found 21 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (78 reviews)
I loved that it was super clean, comfortable, and looked just like the photos. Parking was great as well, thank you for a nice stay.

Reviewed on Jun 13, 2026

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Discover the most popular places to visit in Middlefield

Lyman Orchards

Lyman Orchards

4/5(4 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.

Lyman Orchards

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.

Lyman Meadow Golf Club

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.

Indian Springs Golf Club

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
$107 nightly
The price is $123 total per night from Jun 14 to Jun 15
$123 total
Jun 14 - Jun 15
Total with taxes and fees
9.2/10 Wonderful! (2,184 reviews)
"I love this hotel. It is beautiful, great staff, walking distance to the best of New Haven and affordable. We have stayed there before and will be back again and again! FYI for those of you planning on sampling the “pizza”. It’s called appiza (ah beets) and there is nothing like it in the world. ..."

Reviewed on Jun 12, 2026

New Haven 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
$65 nightly
The price is $75 total per night from Jun 23 to Jun 24
$75 total
Jun 23 - Jun 24
Total with taxes and fees
7.2/10 Good! (1,018 reviews)
"Clean room plenty of parking air conditioning & heat No refrigerator or microwave in room ice machine on 2nd floor a plus a small microwave on 1st floor. I got a break on price through Expedia a plus"

Reviewed on Jun 12, 2026

Motel 6 New Haven - Branford, CT
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $127 total per night from Jun 14 to Jun 15
$127 total
Jun 14 - Jun 15
Total with taxes and fees
7.4/10 Good! (1,373 reviews)
"I checked into the hotel and unfortunately fell in the room, had a knot on the back of my head and broke 2 toes. My cousin contacted the Front Desk and an ambulance came and took me to the hospital. I never had a chance to unpack and stayed in the hospital for 6 days. When I contacted the hotel on ..."

Reviewed on Jun 12, 2026

The Capitol Hotel
See all 1,192 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 $499 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.