Plymouth Vacations from $524
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Your Plymouth Vacation
With plenty of highlights as well as some hidden gems, this city is best experienced with a Plymouth vacation package. Look for places to stay in Litchfield Historic District, which is great for shopping, dining and history. If sightseeing is on the agenda during your trip to Plymouth, check out popular attractions like Black Rock State Park. Stop daydreaming and start traveling. Browse the range of options on Expedia today and put your Plymouth vacation plans into action!
The Latest Plymouth vacation packages
Price found within the past 48 hours. Click for updated prices.
New Haven Hotel
Downtown New Haven
$625
per person
Nov 25 - Nov 30
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (2,294 reviews)
The hotel is well located to all of downtown New Haven and Yale University. The staff is friendly and helpful. The parking garage across the streets that allow guests to park for $24 a day is connected by an enclosed bridge way that takes you to the second floor of the hotel. We chose a king standard room and the bed was extremely comfortable, with a duvet that was light but warm. I would absolutely stay here again.
Reviewed on Sep 19, 2026
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
$909
per person
Nov 25 - Nov 30
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (86 reviews)
Excellent value — a very thoughtfully decorated and well-maintained apartment, effective air conditioning, blackout curtains in every room — really helped the vacation to feel like a “treat”!
I did feel their app / web portal had “quite a lot” baked in it which could feel intimidating at first — vs. a “easy button” version at the top for simple functions like lock/unlock door — but would absolutely consider other Hyatus properties in the future!
Reviewed on Sep 18, 2026
Plymouth Hotel Deals
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
$92 nightly
$106 total
Sep 27 - Sep 28
Total with taxes and fees
Wyndham Southbury
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
$87 nightly
$100 total
Oct 19 - Oct 20
Total with taxes and fees
8.2/10 Very Good! (1,305 reviews)
"The staff were great. The on site restaurant was wonderful"
Reviewed on Sep 19, 2026
Clarion Inn North Haven - New Haven North
201 Washington Avenue North Haven CT
Fully refundable
$110 nightly
$126 total
Oct 11 - Oct 12
Total with taxes and fees
7.4/10 Good! (1,002 reviews)
"The TV didn’t work, it only said no signal on the screen"
Reviewed on Sep 18, 2026
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 Plymouth Vacation Packages
Plymouth Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Population | 12,300 |
Top Sights | Connecticut Valley Winery, Woodbury Ski Area and Pilgrim Mall Shopping Center |
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Frequently asked questions
How much does a Plymouth vacation package cost?
You can pick up a vacation package to this popular destination from $524 on Expedia. But how much your vacation to Plymouth costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Plymouth?
November, December and January are great times to look for cheap Plymouth vacation packages. Traveling in quieter months means you can typically find lower prices on flights and hotels.
How many days is enough for Plymouth?
With a well-planned itinerary, you can easily hit the main Plymouth attractions in a few days. But if you want to discover hidden spots or go on day trips, consider booking your Plymouth vacation for longer.
How to find the best Plymouth package deals?
Begin your search for a Plymouth package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune 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 Plymouth package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Plymouth getaway off to a flying start.
Is it cheaper to book a Plymouth vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Plymouth vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Plymouth?
If you're planning an impromptu Plymouth vacation, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Plymouth vacation packages?
Your Plymouth getaway is meant to be an escape from your busy life, not a reason for money worries. So to allow you that extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs 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.
