Plymouth Vacations from $302

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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.
Homewood Suites by Hilton Wallingford-Meriden

Homewood Suites by Hilton Wallingford-Meriden

3 out of 5
Save 100% on your flight
Price was $376, price is now $302 per person
$302
per person
Jan 10 - Jan 13
found 22 hours ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
9/10 Wonderful! (881 reviews)
Very clean and nice room with a decently appointed kitchen. Great friendly staff. The gym wasn’t so good as there was a loud beeping noise in there both days I went but apart from that everything was great.

Reviewed on Nov 24, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,116, price is now $1,313 per person
$1,313
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
No reviews
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Save 100% on your flight
Price was $631, price is now $424 per person
$424
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to New Haven (HVN)
9/10 Wonderful! (1,874 reviews)
Nice hotel walking distance to everything you might need front desk staff was great as well

Reviewed on Dec 4, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Save 100% on your flight
Price was $597, price is now $404 per person
$404
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
The staff were very friendly. The room was clean. It’s pet friendly which is a plus for us.

Reviewed on Dec 1, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $753, price is now $526 per person
$526
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Nice throwback hotel. Room was spotless, much old school charm. Check in was a little bumpy, otherwise a good stay.

Reviewed on Nov 17, 2025

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Plymouth 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
$82 nightly
The price is $94 total per night from Dec 20 to Dec 21
$94 total
Dec 20 - Dec 21
Total with taxes and fees
8.6/10 Excellent! (1,164 reviews)
Very good

Reviewed on Dec 1, 2025

Holiday Inn Express Southington by IHG
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd Farmington CT
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $105 total per night from Dec 13 to Dec 14
$105 total
Dec 13 - Dec 14
Total with taxes and fees
7.8/10 Good! (999 reviews)
Clean room with a good bed, good shower and an excellent TV

Reviewed on Nov 30, 2025

Extended Stay America Suites Hartford Farmington
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Jan 4 to Jan 5
$107 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8/10 Very Good! (1,057 reviews)
Dog friendly

Reviewed on Dec 1, 2025

Wyndham Southbury
See all 665 properties in Plymouth
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 $302 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.