Roxbury Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Roxbury Vacation
From its rich history to its spectacular views and beyond, there's a whole lot to like about Roxbury. Uncover the wonders of this fascinating city with a Roxbury vacation package that's tailored to you. You'll want to take in some sights during your trip to Roxbury. Don't miss big-name attractions such as Glebe House Museum and The Gertrude Jekyll Garden, Woodbury Ski Area and Pilgrim Mall Shopping Center. Whatever your travel plans or budget, putting together a tailored Roxbury vacation is a cinch with Expedia.
Top Roxbury Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Liberty Inn
Price was CA $755, price is now CA $682 per person
CA $682
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7.6/10 Good! (642 reviews)
The owners are very nice and helpful. The room was clean, the sheets and towels are good quality and were clean as well. There were more than enough pillows and blankets. There is a small table and 2 chairs to sit and look out the window. The bathroom is good size. The water pressure is good, with plenty of hot water. The floor is tiled, so it is very cold on bare feet. There is no breakfast, but they will get you bottled water if you ask. The parking is well lit. You can hear the traffic from the highway, especially the trucks. I like the sound. If sound bothers you, you, may want to bring ear plugs. Overall, this is a wonderful place to stay. I have been coming here for years.
Reviewed on Apr 7, 2026
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was CA $973, price is now CA $744 per person
CA $744
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very Good! (1,007 reviews)
Great place to stay on the shoreline. Privately owned so you.are supporting local businesses!
Reviewed on Apr 10, 2026
Roxbury Hotel Deals
Litchfield County Four Season Country Paradise
Roxbury CT
9.4/10 Exceptional! (51 reviews)
The good, the bad and the really ugly. The good: this house worked for our overall purpose; a family thanksgiving with the people who actually stayed in the house using the kitchen for turkey and pies. The rest of the meal was prepared off site. We were able to seat all sixteen people, and as hoped ...
Reviewed on Dec 15, 2025
Best Western Danbury/Bethel
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Apr 26 to Apr 27
CA $129
CA $148 total
Apr 26 - Apr 27
includes taxes & fees
7.8/10 Good! (1,001 reviews)
Breakfast was very good
Reviewed on Apr 15, 2026
Hilton Garden Inn Shelton
25 Old Stratford Rd Shelton CT
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Apr 26 to Apr 27
CA $169
CA $194 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (1,098 reviews)
satisfied
Reviewed on Apr 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
