Plymouth Vacation Packages
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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!
Top Plymouth Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Old Saybrook
Price was CA $994, price is now CA $945 per person
CA $945
per person
Jul 28 - Aug 3
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
7/10 Good! (921 reviews)
This is exactly what I would expect from a super eight. It was clean safe comfortable bed. Also AC worked good bathroom was cleaned. They don’t have breakfast being served there, but that’s not an issue for me. It’s in a safe location. Very close to downtown old Saybrook that has a lot of beautiful restaurants and shopping for the value. I would stay here again.
Reviewed on Jun 7, 2026
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was CA $1,408, price is now CA $1,116 per person
CA $1,116
per person
Jul 28 - Aug 3
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very Good! (1,004 reviews)
Friendly staff, clean room, nice location
Reviewed on Jun 3, 2026
Quality Inn Old Saybrook - Westbrook
Price was CA $1,145, price is now CA $1,142 per person
CA $1,142
per person
Jul 28 - Aug 3
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
7.8/10 Good! (1,002 reviews)
The room was very clean and quiet. The interior was modern and very well laid out. The breakfast was very good.
Reviewed on Jun 8, 2026
Plymouth Hotel Deals
Cozy Lakefront Bungalow w firepit/dock/kayaks
Plymouth CT
10/10 Exceptional! (46 reviews)
"This place was absolutely amazing! First and foremost, its pet-friendly! The views are breathtaking and the master bedroom is everything you could dream of. The hosts were so friendly and easy to communicate with. There really is everything youd need to enjoy some time away. Everything was very neat ..."
Reviewed on Apr 27, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundable
The price is CA $131 per night from Jun 28 to Jun 29
CA $131
CA $150 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (1,329 reviews)
","
Reviewed on Jun 10, 2026
Courtyard by Marriott Waterbury Downtown
63 Grand St Waterbury CT
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Jun 21 to Jun 22
CA $138
CA $159 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (1,239 reviews)
"Overall a good stay with attentive staff"
Reviewed on Jun 7, 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.
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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.
