Plymouth Vacations from $489
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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.
Hyatus Luxury Residences City Crossing
The Hill
Price was $860, price is now $692 per person
$692
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
9.2/10 Wonderful! (35 reviews)
Bed had no mattress cover but was very comfortable. Only one working lamp. Vents could use a good cleaning. I would recommend it and would stay again.
Reviewed on Oct 25, 2026
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
Price was $831, price is now $681 per person
$681
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
9.6/10 Exceptional! (91 reviews)
We stayed for a week and had a great trip, apartment was clean and cozy and the bathroom was very big. When we come back we will consider staying here again
Reviewed on Oct 26, 2026
Landing Apartments New Haven Near Dixwell
Newhallville
Price was $1,016, price is now $881 per person
$881
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.
Reviewed on May 25, 2026
Plymouth Hotel Deals
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundable
$96 nightly
The price is $110 total per night from Dec 4 to Dec 5
$110 total
Dec 4 - Dec 5
Total with taxes and fees
8.6/10 Excellent! (1,467 reviews)
"Room was clean, desk staff was very helpful. Needed to change our room do to a crying baby. The front desk was very accommodating in finding a quieter room. There was plenty of breakfast options. Lots of parking. Would highly recommend !"
Reviewed on Nov 2, 2026
Heritage Hotel, Golf & Conference Center
522 Heritage Road Southbury CT
$130 nightly
The price is $149 total per night from Nov 5 to Nov 6
$149 total
Nov 5 - Nov 6
Total with taxes and fees
Courtyard by Marriott Waterbury Downtown
63 Grand St Waterbury CT
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Nov 5 to Nov 6
$102 total
Nov 5 - Nov 6
Total with taxes and fees
8.6/10 Excellent! (1,293 reviews)
"I would definitely stay there again"
Reviewed on Nov 3, 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
