Roxbury Vacations from $308

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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 $400, price is now $308 per person
$308
per person
Jul 24 - Jul 26
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to New Haven (HVN)
9.2/10 Wonderful! (2,140 reviews)
Thin walls with horrible noise blocking. Otherwise is ok.

Reviewed on Jun 1, 2026

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $915, price is now $683 per person
$683
per person
Aug 21 - Aug 23
found 5 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.2/10 Wonderful! (31 reviews)
Great stay with many amenities to enjoy within the building!

Reviewed on Apr 3, 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 $951, price is now $719 per person
$719
per person
Aug 21 - Aug 23
found 5 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.6/10 Exceptional! (73 reviews)
Excellent communication and exceptionally clean. Highly recommended for safe and secure stay. We stayed for 3 weeks while my son recovered from surgery at Yale New Haven. A bit pricey for the area, but it felt very safe and comfortable.

Reviewed on Jun 3, 2026

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $1,354, price is now $1,027 per person
$1,027
per person
Aug 21 - Aug 23
found 5 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.4/10 Exceptional! (369 reviews)
Exceptionally clean and wonderful staff

Reviewed on May 10, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $514, price is now $400 per person
$400
per person
Aug 21 - Aug 23
found 5 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.2/10 Wonderful! (988 reviews)
Beautiful, boutique style hotel! Great cafe inside. Definitely worth the stay!

Reviewed on Jun 1, 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

Get rates
Litchfield County Four Season Country Paradise
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $119 total per night from Jun 21 to Jun 22
$119 total
Jun 21 - Jun 22
Total with taxes and fees
8/10 Very Good! (1,232 reviews)
"Our stay was only for one night, and I would stay there again."

Reviewed on Jun 3, 2026

Ethan Allen Hotel
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
$99 nightly
The price is $114 total per night from Jun 21 to Jun 22
$114 total
Jun 21 - Jun 22
Total with taxes and fees
8.4/10 Very Good! (1,232 reviews)
"Solo traveler I went for 4 days to hang out in CT. This location was close to what I needed. Staff are nice and property is definitely 3 star headed towards 2 stars .. but it gets the job done for the stay. There are no microwaves You can park in the garage for free if you don’t tell the front desk ..."

Reviewed on Jun 2, 2026

Courtyard by Marriott Waterbury Downtown
See all 695 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 $308 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.