Roxbury Vacation Packages
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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.
Red Roof Inn Milford - New Haven
Price was CA $1,217, price is now CA $1,172 per person
CA $1,172
per person
Jun 27 - Jul 1
found 14 hours ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
7/10 Good! (1,003 reviews)
The ice machine wasn't working. Neither one. Bur the staff was so nice!! It was clean and close to everything.. I will definitely stay there again.
Reviewed on Apr 12, 2026
Springhill Suites Milford
Price was CA $1,567, price is now CA $1,527 per person
CA $1,527
per person
Jun 27 - Jul 1
found 14 hours ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
8.6/10 Excellent! (1,000 reviews)
Clean modern room. Spacious bathroom. Staff very friendly. Nice selection for breakfast.
Reviewed on Apr 8, 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 $121 per night from Apr 19 to Apr 20
CA $121
CA $139 total
Apr 19 - Apr 20
includes taxes & fees
7.8/10 Good! (1,012 reviews)
Comfortable
Reviewed on Apr 12, 2026
Hilton Garden Inn Shelton
25 Old Stratford Rd Shelton CT
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Apr 27 to Apr 28
CA $168
CA $193 total
Apr 27 - Apr 28
includes taxes & fees
8/10 Very Good! (1,101 reviews)
The first room/first night the heater was stuck. It kept getting hotter and hotter and we couldn’t turn it off. Called the front desk and the only solution was to move rooms but it was 3ish in the morning. I finally googled how to turn it off manually and took off the front of the heater to find ...
Reviewed on Apr 13, 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.
