Roxbury Vacations from $263

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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.
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 $310, price is now $263 per person
$263
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8/10 Very Good! (1,409 reviews)
My 3, well (2½) day stay was overall not bad untill........ On My 2 day of booking the room i was asked by the the woman with a clip board who im assuming was the head of in house keeping if i was staying for another day which i had told her yes and she asked would i be needing house keeping to go in my room which i replied no alls i need is fresh towels......

Reviewed on Oct 30, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $1,626, price is now $1,057 per person
$1,057
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
The Surfside Hotel

The Surfside Hotel

2 out of 5
Lordship
Price was $394, price is now $323 per person
$323
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.4/10 Exceptional! (163 reviews)
Everyone was friendly and the facility was nice and clean. We would stay again.

Reviewed on Oct 20, 2025

Sleep Inn & Suites Niantic

Sleep Inn & Suites Niantic

2.5 out of 5
Price was $406, price is now $348 per person
$348
per person
Jan 21 - Jan 24
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
8.4/10 Very Good! (1,008 reviews)
Small breakfast area lacked enough seating but otherwise a great stop near the casino.

Reviewed on Oct 15, 2025

The Niantic Inn

The Niantic Inn

2 out of 5
Price was $554, price is now $480 per person
$480
per person
Jan 21 - Jan 24
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
9/10 Wonderful! (113 reviews)
The boardwalk and beach can be reached a short walk across Main street through a parking lot and the "hole in the wall" under railroad tracks. Thisisnot the season for lounging on a beach but a walk on the boardwalk is nice. I always enjoy watching the trains go by.

Reviewed on Oct 26, 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! (50 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 Nov 3 to Nov 4
$102 total
Nov 3 - Nov 4
Total with taxes and fees
8/10 Very Good! (1,035 reviews)
Nice clean hotel
The room was clean and well maintained. The only problem was that the fan in the bathroom came on when the light was turned on which made it noisy. It may have been hooked in wrong because there was a switch next to it but it didn’t do anything when it was turned on.

Reviewed on Oct 27, 2025

Microtel Inn & Suites by Wyndham Bethel/Danbury
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 Nov 9 to Nov 10
$107 total
Nov 9 - Nov 10
Total with taxes and fees
8/10 Very Good! (1,010 reviews)
Room & Building were very clean. Staff was friendly.

Reviewed on Oct 24, 2025

Wyndham Southbury
See all 651 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 $263 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.