Roxbury Vacations from $362

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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.
Clarion Inn

Clarion Inn

3 out of 5
Price was $415, price is now $362 per person
$362
per person
May 17 - May 19
just found
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
7.6/10 Good! (1,002 reviews)
Amazing staff and rooms

Reviewed on Feb 15, 2026

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $1,880, price is now $1,419 per person
$1,419
per person
May 17 - May 19
just found
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (21 reviews)
The place could have been a little cleaner I found hair in the bed and crumbs and dirt in the couch and under it as well the walls were stained and the carpet was stained in the bedroom it definitely was a big difference from the first time I stayed there

Reviewed on Feb 16, 2026

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was $494, price is now $406 per person
$406
per person
May 17 - May 19
just found
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8/10 Very Good! (1,457 reviews)
everything in the hotel was amazing until the night staff arrived i went down to ask for another roll of toilet paper and he said he couldn’t go get any and told us we could use the downstairs lobby bathroom if we needed to use it

Reviewed on Feb 24, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $2,047, price is now $1,778 per person
$1,778
per person
May 17 - May 19
just found
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (60 reviews)
Everything here has been excellent. I am a travel nurse and they have really helped to make my trip here the best.

Reviewed on Feb 27, 2026

Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

3 out of 5
The Centre
Price was $622, price is now $545 per person
$545
per person
May 17 - May 19
just found
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (428 reviews)
The room was good sized and clean. The body wash was empty in the bathroom. Otherwise we had a great dtay

Reviewed on Mar 1, 2026

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Roxbury Hotel Deals

Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road Danbury CT
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $180 total per night from Mar 10 to Mar 11
$180 total
Mar 10 - Mar 11
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
Room was spotless, staff were friendly. The only thing that I disliked about the experience was the noise coming from other rooms. Also there was no ice dispenser on the 2nd floor so you had to walk all the way back to the lobby or 3rd floor to get a bucket of ice. They could install better shower ...

Reviewed on Feb 20, 2026

Hotel Zero Degrees Danbury
Hyatt House Shelton

Hyatt House Shelton

3 out of 5
830 Bridgeport Ave Shelton CT
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $132 total per night from Mar 8 to Mar 9
$132 total
Mar 8 - Mar 9
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
Nice size room

Reviewed on Feb 28, 2026

Hyatt House Shelton
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St Waterbury CT
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Mar 2 to Mar 3
$102 total
Mar 2 - Mar 3
Total with taxes and fees
8.4/10 Very Good! (1,139 reviews)
The room was a little chilly. The heat couldn’t keep up.

Reviewed on Feb 24, 2026

Courtyard by Marriott Waterbury Downtown
See all 676 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 $362 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.

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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.