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.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was CA $947, price is now CA $917 per person
CA $917
per person
Apr 14 - Apr 18
found 16 hours ago
Roundtrip flight included
Calgary (YYC) to New Haven (HVN)
8/10 Very Good! (1,002 reviews)
Very nice check in and check out
Room refurbished/clean and comfortable
Would stay again
Reviewed on Feb 16, 2026
Quality Inn Old Saybrook - Westbrook
Price was CA $1,032, price is now CA $1,027 per person
CA $1,027
per person
Apr 14 - Apr 18
found 16 hours ago
Roundtrip flight included
Calgary (YYC) to New Haven (HVN)
7.8/10 Good! (1,003 reviews)
Snow/ice removal was poor causing long walk to the room. Also, parking was at a premium b cause parts of the lot were not plowed well.
Everyone wanted to park on one quadrant of he lot since we all used the main lobby door. Room had a musty smell and tv was small and sound was not good. Only a half roll of tp
Reviewed on Feb 16, 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
Hotel Zero Degrees Danbury
15 Milestone Road Danbury CT
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Mar 1 to Mar 2
CA $202
CA $233 total
Mar 1 - Mar 2
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
Great room, beautiful facility, excellent restaurant, professional staff
Reviewed on Feb 17, 2026
Courtyard by Marriott Waterbury Downtown
63 Grand St Waterbury CT
The price is CA $121 per night from Mar 1 to Mar 2
CA $121
CA $140 total
Mar 1 - Mar 2
includes taxes & fees
8.4/10 Very Good! (1,135 reviews)
Clean and comfortable. Great stay.
Reviewed on Feb 15, 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.
