Roxbury Vacations from $570

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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.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $741, price is now $570 per person
$570
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (2,115 reviews)
We weren’t happy that parking was $24 a day and that the only part of the breakfast that was free was the coffee. Otherwise, everything else was fine.

Reviewed on May 12, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $3,752, price is now $2,423 per person
$2,423
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
Las Flores Villa

Las Flores Villa

5 out of 5
Save 100% on your flight
Price was $3,881, price is now $2,517 per person
$2,517
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
10/10 Exceptional! (1 review)
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $1,371, price is now $998 per person
$998
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
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 $1,290, price is now $953 per person
$953
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.6/10 Exceptional! (69 reviews)
I had a great stay at this property overall. The room was clean, comfortable, and well-maintained, which made it easy to relax after a long day. The staff was friendly and helpful, always willing to answer questions and make sure everything was taken care of. The kitchen was stocked with the basics needed for cooking, which was convenient during the stay. Parking was also easy to access and felt safe, which was a big plus. The location was convenient, close to nearby attractions, restaurants, and stores. If I had to mention one thing for improvement, it would be minor updates to some areas to make the space feel a bit more modern. Overall, I would definitely recommend this property and would consider staying here again in the future.

Reviewed on May 5, 2026

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Roxbury Hotel Deals

Litchfield County Four Season Country Paradise

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

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Litchfield County Four Season Country Paradise
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $109 total per night from May 24 to May 25
$109 total
May 24 - May 25
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
Decent stay. Room was HUGE!

Reviewed on May 9, 2026

Best Western Danbury/Bethel
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St Waterbury CT
$89 nightly
The price is $102 total per night from May 26 to May 27
$102 total
May 26 - May 27
Total with taxes and fees
8.4/10 Very Good! (1,212 reviews)
My go to spot for family and friends when they come to visit.

Reviewed on May 11, 2026

Courtyard by Marriott Waterbury Downtown
See all 705 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 $570 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.