Terryville Vacations from $277

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Your Terryville Vacation

Say goodbye to planning hassles and hello to a Terryville vacation package. With everything organized before you go, you can focus on discovering this city, starting with Litchfield Historic District, which is good for shopping, dining and history. Fill your trip to Terryville with tours of its most popular attractions. First stop? Make a move for Black Rock State Park. Stop dreaming and start doing. Browse the many options on Expedia today and put your Terryville vacation plans into motion!

The Latest Terryville vacation packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
Price was $300, price is now $277 per person
$277
per person
Feb 27 - Mar 1
found 18 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
6.2/10 (1,000 reviews)
everything was very good.

Reviewed on Dec 17, 2025

The Surfside Hotel

The Surfside Hotel

2 out of 5
Lordship
Price was $422, price is now $359 per person
$359
per person
Feb 27 - Mar 1
found 18 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.4/10 Exceptional! (168 reviews)
Bed was very comfortable... TV was dysfunctional with 2 remotes. Restaurant / Bar attached to Hotel was nice.

Reviewed on Nov 20, 2025

Residence Inn by Marriott Milford

Residence Inn by Marriott Milford

3 out of 5
Price was $359, price is now $332 per person
$332
per person
Feb 27 - Mar 1
found 18 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (459 reviews)
Clean room friendly staff

Reviewed on Sep 30, 2025

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Terryville Hotel Deals

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

2.5 out of 5
325 Main St Terryville CT
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $86 total per night from Dec 29 to Dec 30
$86 total
Dec 29 - Dec 30
Total with taxes and fees
7.6/10 Good! (178 reviews)
Yea it was clean

Reviewed on Dec 7, 2025

PLYMOUTH MOTOR LODGE
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Dec 28 to Dec 29
$102 total
Dec 28 - Dec 29
Total with taxes and fees
7.4/10 Good! (1,119 reviews)
Great location and a very clean and comfortable room. The staff was very helpful and went out of their way to help me.

Reviewed on Dec 17, 2025

The Capitol 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
$82 nightly
The price is $94 total per night from Jan 2 to Jan 3
$94 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
8.6/10 Excellent! (1,178 reviews)
Front desk

Reviewed on Dec 22, 2025

Holiday Inn Express Southington by IHG
See all 769 properties in Terryville
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 Terryville Vacation Packages

Terryville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
5,400
Top Sights
Connecticut Valley Winery, Jerram Winery and Flanders Nature Center

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Frequently asked questions

How much does a Terryville vacation package cost?
You can grab a vacation package to this destination from $277 on Expedia. But how much your vacation to Terryville costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Terryville?
You can generally find reduced prices and better availability in November, December and January. Browse our cheap Terryville vacation packages and you could score some great off-season discounts.
How many days is enough for Terryville?
The ideal duration of your Terryville vacation depends on what you'd like to do. Typically, a few days to a week will give you time to check out all the top sights and explore some hidden gems along the way.
How to find the best Terryville package deals?
Use Expedia's handy filters to find some fabulous Terryville package deals. When you start your search, just 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 Terryville package deals in the low season. Play around with 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 as soon as possible.
Is it cheaper to book a Terryville vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations separately. Better still, you can personalize your Terryville getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Terryville?
If you're planning a spur-of-the-moment Terryville vacation, 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 find sensational deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Terryville vacation packages?
Your Terryville trip should be a relaxing escape from your busy life, not a source of money worries. So to give you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.