Oxford Vacation Packages
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Your Oxford Vacation
With every last detail planned before you take off, our Oxford vacation packages mean you can focus more on having fun. Whether you're going to be based in the neighborhood of Cheshire Historic District, which is great for history, or somewhere else in town, this lively city offers a wealth of discoveries. Eager to get out and explore? Southford Falls State Park, Hop Brook Lake and Kettletown State Park are just three of the top-rated places to visit during a trip to Oxford. Browse Expedia's wide range of travel options and start planning your perfect vacation to Oxford now.
Top Oxford Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was CA $1,383, price is now CA $957 per person
CA $957
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
We have been coming here for years and it is the best it’s ever been! Staff is friendly and accommodating. The rooms have been renovated and clean.
Reviewed on May 17, 2026
Head of Pond House
Price was CA $3,985, price is now CA $3,270 per person
CA $3,270
per person
Jun 18 - Jun 21
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
10/10 Exceptional! (7 reviews)
Very special property. One of my favorites. Beautiful, exceptionally clean and in a gorgeous location. Host was exceptional and communication excellent.
Reviewed on May 9, 2026
The Scranton Seahorse Inn
Madison Center
Price was CA $2,011, price is now CA $1,785 per person
CA $1,785
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9/10 Wonderful! (242 reviews)
We had a wonderful stay. Perfect location, great staff, and check-in process, and our room was delightful.
Reviewed on Apr 22, 2026
Saybrook Point Resort & Marina
Old Saybrook Center
Price was CA $2,861, price is now CA $2,550 per person
CA $2,550
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.6/10 Exceptional! (1,002 reviews)
We ended up getting an upgrade into one of the two bedroom two bathroom pillows due to the renovation on the main hotel. We were pleasantly surprised we felt like we were home. It was so nice so relaxing. Everything was amazing and we could literally walk right across the street to get something to eat at fresh salt or at the choo-choo lounge views of the water at home field by having a full kitchen and laundry felt like a great little mini vacation we’ve been there before and we will be back again. Bravo.
Reviewed on May 17, 2026
Oxford Hotel Deals
New Haven Hotel
229 George Street New Haven CT
The price is CA $174 per night from May 25 to May 26
CA $174
CA $200 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (2,140 reviews)
"Very clean and nice property. Uber does not go here and you have to use Lift."
Reviewed on May 19, 2026
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
The price is CA $209 per night from May 24 to May 25
CA $209
CA $240 total
May 24 - May 25
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Frequent traveler here. This is not a 4-star hotel. During my stay, housekeeping took my newly purchased mascara ($40+) and one of my organic face towels. I spoke with several people, but no one followed up and no compensation was offered. Disappointing experience."
Reviewed on May 17, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from May 28 to May 29
CA $148
CA $171 total
May 28 - May 29
includes taxes & fees
8.6/10 Excellent! (1,304 reviews)
"Staff was attentive and professional. Will go back again"
Reviewed on May 16, 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.
