Thomaston Vacations from $399

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Your Thomaston Vacation

Say bye-bye to the stress of planning and hello to a Thomaston vacation package. With your travel details organized before you go, you can focus on discovering this city, starting with Litchfield Historic District, which is good for shopping, dining and history. If sightseeing is on your list of things to do during your trip to Thomaston, check out well-known attractions like Black Rock State Park. Your Thomaston vacation is clicks away. Explore hotels, flights and more on Expedia for an adventure that's tailored to suit your travel style.

The Latest Thomaston vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Branford-New Haven by IHG

Holiday Inn Express Branford-New Haven by IHG

3 out of 5
Price was $438, price is now $399 per person
$399
per person
May 8 - May 10
found 10 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (1,001 reviews)
Booked specifically for the pool and it was out of service when we arrived.

Reviewed on Feb 22, 2026

Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

3.5 out of 5
Save 100% on your flight
Price was $703, price is now $557 per person
$557
per person
May 4 - May 11
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.4/10 Very Good! (1,004 reviews)
Room and hotel needs upgrade. Staff was very good. Breakfast overpriced, but nothing else close. If you are visiting Heritage Village, this is most convenient.

Reviewed on Feb 25, 2026

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $988, price is now $856 per person
$856
per person
May 4 - May 11
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
Comfortable, clean, quiet. Perfect atay

Reviewed on Feb 23, 2026

Homewood Suites by Hilton Orange New Haven

Homewood Suites by Hilton Orange New Haven

3 out of 5
Price was $485, price is now $457 per person
$457
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (1,000 reviews)
Hotel is clean, pool is nice, breakfast is good and staff are friendly!

Reviewed on Feb 26, 2026

Springhill Suites Milford

Springhill Suites Milford

3 out of 5
Price was $535, price is now $530 per person
$530
per person
Apr 1 - Apr 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.6/10 Excellent! (1,001 reviews)
This was my second time staying here, room was clean, staff was nice, and the breakfast was good, its a plus when breakfast is included.

Reviewed on Feb 24, 2026

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Thomaston Hotel Deals

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $100 total per night from Mar 3 to Mar 4
$100 total
Mar 3 - Mar 4
Total with taxes and fees
8.6/10 Excellent! (1,219 reviews)
Easy check in, rooms clean,

Reviewed on Feb 27, 2026

Holiday Inn Express Southington by IHG
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St Waterbury CT
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Mar 1 to Mar 2
$102 total
Mar 1 - Mar 2
Total with taxes and fees
8.4/10 Very Good! (1,139 reviews)
The room was a little chilly. The heat couldn’t keep up.

Reviewed on Feb 24, 2026

Courtyard by Marriott Waterbury Downtown
Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St Meriden CT
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $99 total per night from Feb 28 to Mar 1
$99 total
Feb 28 - Mar 1
Total with taxes and fees
Red Roof Inn Meriden
See all 719 properties in Thomaston
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 Thomaston Vacation Packages

Thomaston Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
1,900
Top Sights
Connecticut Valley Winery, Woodbury Ski Area and Pilgrim Mall Shopping Center

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Frequently asked questions

How much does a Thomaston vacation package cost?
Offering great value package deals from $399 on Expedia, you'll be thrilled with how little a vacation to Thomaston costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Thomaston?
You can typically find lower prices and greater availability in November, December and January. Take a look at our cheap Thomaston vacation packages and you could score some great off-season deals.
How many days is enough for Thomaston?
With a well-planned schedule, you can easily hit the most popular Thomaston attractions in a handful of days. But if you'd like to discover hidden gems or go on day tours, think about booking your Thomaston vacation for longer.
How to find the best Thomaston package deals?
Start your search for a Thomaston package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Thomaston package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Thomaston escape off to a flying start.
Is it cheaper to book a Thomaston vacation as a package?
You can enjoy significant savings on your next Thomaston retreat by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Thomaston?
If you've got your Thomaston vacation dates locked in, book as early as you can to grab some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Thomaston vacation packages?
If you're like us, you love discovering new places but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Thomaston vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.

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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.