Roxbury Vacations from $370

Book a Hotel + Flight or Car together to unlock savings

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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 Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,014 reviews)
Everything was great, the rooms where clean, the staff was awesome

Reviewed on Jul 9, 2025

Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (412 reviews)
It was close to shopping and restaurants.

Reviewed on May 2, 2025

HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
9/10 Wonderful! (1,004 reviews)
Very easy navigation to the hotel. Got exactly the room that I reserved, and even a little bit better. The hotel staff from front desk agent to assistant general manager to bartender to the breakfast hostess Were all incredibly friendly and warm and responsive. It felt like staying at a friend's place. Their last act upon our checkout was reflective of the service throughout our Multi-day stay: I asked if the breakfast coffee was still out and the front desk agent told me it was not but then offered to get me a cup of coffee from the kitchen, which she did right away and with a smile. It was so nice and such a kind gesture to this weary traveler, and it's the little things like that that make this a great place to stay.

Reviewed on Jul 10, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
The view was stunning and the hotel was very clean. Would definitely stay again

Reviewed on Jun 18, 2025

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
8.6/10 Excellent! (548 reviews)
Overall, a great experience. Staff were professional and addressed every question. This Residence Inn allows pets, which was key.

Reviewed on Jun 14, 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! (40 reviews)
Great place
"As advertised, easy place to hang with friends."

Reviewed on Jul 6, 2025

Get rates
Litchfield County Four Season Country Paradise
Wyndham Southbury
Wyndham Southbury
3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Jul 27 to Jul 28
$107 total
Jul 27 - Jul 28
Total includes taxes and fees
8/10 Very Good! (1,010 reviews)
"The staff there was very helpful. The cleaning staff was excellent also. The rooms were beautiful. We loved the pool. Thank you to everyone."

Reviewed on Jul 10, 2025

Wyndham Southbury
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
$111 nightly
The price is $127 total per night from Jul 20 to Jul 21
$127 total
Jul 20 - Jul 21
Total includes taxes and fees
7.8/10 Good! (1,003 reviews)
"Great stay"

Reviewed on Jul 11, 2025

Hilton Garden Inn Shelton
See all 645 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.

Find the Best Roxbury Vacation Packages

Roxbury Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Lake Waramaug State Park, Lovers Leap State Park and Woodbury Ski Area

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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 $370 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.