Plymouth Vacations from $514

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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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $677, price is now $514 per person
$514
per person
Jun 1 - Jun 6
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
8/10 Very Good! (1,004 reviews)
Very welcoming staff. Average accommodations but comfortable and convenient to supermarket.

Reviewed on Mar 9, 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 $899, price is now $650 per person
$650
per person
Jun 11 - Jun 15
found 21 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
8.6/10 Excellent! (1,008 reviews)
My wife had a procedure at Yale New Haven and I only one night. It was very convenient and pleasant. I only used the room. Not the bar or restaurant.

Reviewed on Mar 18, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $755, price is now $556 per person
$556
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (958 reviews)
Groovy, fun, comfortable hotel in a great location.

Reviewed on Mar 3, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $1,159, price is now $867 per person
$867
per person
Jun 11 - Jun 15
found 21 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.6/10 Exceptional! (64 reviews)
Everything here has been excellent. I am a travel nurse and they have really helped to make my trip here the best.

Reviewed on Feb 27, 2026

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Save 100% on your flight
Price was $761, price is now $578 per person
$578
per person
Jun 11 - Jun 15
found 21 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
No reviews
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Plymouth Hotel Deals

Cozy Lakefront Bungalow w firepit/dock/kayaks

Cozy Lakefront Bungalow w firepit/dock/kayaks

Plymouth CT
10/10 Exceptional! (42 reviews)
Great location for a winter retreat! Property is as pictured. Host is prompt in communication for any questions. Home is well equipped. Bonus on New Years Eve after midnight - fireworks from other side of the lake!

Reviewed on Jan 4, 2026

Get rates
Cozy Lakefront Bungalow w firepit/dock/kayaks
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$116 nightly
The price is $133 total per night from Apr 3 to Apr 4
$133 total
Apr 3 - Apr 4
Total with taxes and fees
8.6/10 Excellent! (1,237 reviews)
Everything was clean and nice. The room was very large. The bed was very comfortable and the breakfast was a nice touch, would definitely stay there again if I’m in the area.

Reviewed on Mar 20, 2026

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
$103 nightly
The price is $118 total per night from Mar 29 to Mar 30
$118 total
Mar 29 - Mar 30
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
The rooms weren’t dirty, they were worn, old. I liked the setup. We had to be moved from our first room because the tv didn’t work. I would stay again but for a weekend tops. I have a bit of OCD so next time I would bring my own cleaning supplies and sheets. All in all the hotel was ok, the staff ...

Reviewed on Mar 19, 2026

Extended Stay America Suites Hartford Farmington
See all 698 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 $514 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.