Roxbury Vacations from $223

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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.

The Latest Roxbury vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $261, price is now $223 per person
$223
per person
Oct 26 - Oct 28
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
8.4/10 Very Good! (1,004 reviews)
I enjoyed my stay at the holiday inn Cheshire location. It is in a great location with plenty of options for food, drinks, and things to do near by. Easy access to the highway which is a plus. The gym is limited with not too many options to get in a good workout but, enough to get some cardio in. The staff is excellent very pleasant and kind. The hotel bar offers a good list of different beer wine and liquor to enjoy as well as some food options. I stayed for a total of 5 nights and it went great! The only complaint I have is my room key did not always work to enter my room. The staff mentioned they have been having issues and are working on getting it resolved it was just inconvenient when coming back to my room with my hands full and having to go back downstairs to get my key reactivated. Overall I really enjoyed my stay and looking forward to staying again when I am back in town!

Reviewed on Sep 18, 2025

Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
Price was $625, price is now $510 per person
$510
per person
Oct 23 - Oct 27
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (432 reviews)
Went for a wedding and was stranded at the venue from the hotel! It wasn’t until I threatened them with a lawsuit and amazingly they found a way to get back to the venue but that was after I spent $40 on an Uber. The hotel was nice but extremely noisy with the highway right next door. If you build a hotel next to a highway you should sound proof your property!!

Reviewed on Sep 18, 2025

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $792, price is now $676 per person
$676
per person
Nov 25 - Nov 30
found 14 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.6/10 Excellent! (1,102 reviews)
Bulbs in the elevator need replacing

Reviewed on Sep 18, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $577, price is now $510 per person
$510
per person
Oct 23 - Oct 27
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,083 reviews)
Easy access from the interstate. Very close to the cute downtown with nice restaurants

Reviewed on Sep 16, 2025

Clarion Inn

Clarion Inn

3 out of 5
Price was $588, price is now $523 per person
$523
per person
Nov 11 - Nov 15
found 19 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
7.6/10 Good! (1,015 reviews)
It was an average place to stay, staff were friendly

Reviewed on Sep 16, 2025

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Roxbury Hotel Deals

Litchfield County Four Season Country Paradise

Litchfield County Four Season Country Paradise

Roxbury
9.4/10 Exceptional! (48 reviews)
"Great time for all. Hosts were great."

Reviewed on Sep 3, 2025

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Litchfield County Four Season Country Paradise
Microtel Inn & Suites by Wyndham Bethel/Danbury

Microtel Inn & Suites by Wyndham Bethel/Danbury

2 out of 5
80 Benedict Rd, Bethel, CT
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Sep 22 to Sep 23
$102 total
Sep 22 - Sep 23
Total with taxes and fees
8/10 Very Good! (1,008 reviews)
"Clean room but terrible breakfast."

Reviewed on Sep 12, 2025

Microtel Inn & Suites by Wyndham Bethel/Danbury
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd, Shelton, CT
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $146 total per night from Sep 28 to Sep 29
$146 total
Sep 28 - Sep 29
Total with taxes and fees
7.8/10 Good! (1,010 reviews)
"The whole experience was great. Staff was friendly and helpful. Sitting area outside and inside was perfect, very good bacon,egg and chesse on a roll cooked made to order"

Reviewed on Sep 14, 2025

Hilton Garden Inn Shelton
See all 660 properties in Roxbury
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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Frequently asked questions

How much does a Roxbury vacation package cost?
You can snap up a vacation package to this popular destination from $223 on Expedia. But how much your vacation to Roxbury costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Roxbury?
If you'd like to score a cheap Roxbury vacation package, consider traveling in November, December and January. You'll generally find better prices on accommodations and flights during these months — perfect for budget-conscious travelers.
How many days is enough for Roxbury?
With a well-organized schedule, you can easily hit the main Roxbury attractions in a handful of days. But if you'd like to explore off the beaten track or take day trips, think about booking your Roxbury vacation for longer.
How to find the best Roxbury package deals?
Use Expedia's filter tool to help you find some great Roxbury package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Roxbury package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Roxbury vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights separately. Better still, you can personalize your Roxbury getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Roxbury?
Land fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Roxbury getaway.
Does Expedia offer Book Now, Pay Later Roxbury vacation packages?
Your Roxbury break should be a relaxing escape from your daily routine, not a reason for money worries. So to allow you extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

Explore a world of travel with Expedia

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.