Thomaston Vacations from $316

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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.

Landing Modern 2bd, Gym

3 out of 5
West New Haven
Save 100% on your flight
Price was $401, price is now $316 per person
$316
per person
Feb 12 - Feb 14
found 5 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
No reviews
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $645, price is now $489 per person
$489
per person
Mar 31 - Apr 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Great staff, convenient central location, and tasteful retro-collegiate decor in a renovated historic building.

Reviewed on Jan 1, 2026

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $523, price is now $408 per person
$408
per person
Mar 31 - Apr 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
8.6/10 Excellent! (1,184 reviews)
The front desk employees were very nice and the room was clean and comfortable. Breakfast was just okay.

Reviewed on Jan 11, 2026

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was $455, price is now $379 per person
$379
per person
Mar 31 - Apr 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
8/10 Very Good! (1,457 reviews)
Good spot can’t complain about it

Reviewed on Jan 10, 2026

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $685, price is now $575 per person
$575
per person
Feb 13 - Feb 16
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
Clean and nice! Really appreciated the bath robes.

Reviewed on Jan 2, 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 refundable
$87 nightly
The price is $100 total per night from Feb 1 to Feb 2
$100 total
Feb 1 - Feb 2
Total with taxes and fees
8.6/10 Excellent! (1,195 reviews)
Clean comfortable room, friendly staff, great breakfast

Reviewed on Jan 2, 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 Jan 25 to Jan 26
$102 total
Jan 25 - Jan 26
Total with taxes and fees
8.2/10 Very Good! (1,101 reviews)
The staff were great I had a problem with my first room and had to change rooms. I wasn’t happy about the inconvenience but overall my stay was good. The parking was a pain to far in the cold.

Reviewed on Jan 9, 2026

Courtyard by Marriott Waterbury Downtown
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd Farmington CT
$80 nightly
The price is $92 total per night from Feb 2 to Feb 3
$92 total
Feb 2 - Feb 3
Total with taxes and fees
7.8/10 Good! (999 reviews)
Great place.

Reviewed on Jan 2, 2026

Extended Stay America Suites Hartford Farmington
See all 699 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 $316 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.