
Roxbury Vacations from $867
Book a Hotel + Flight or Car together to unlock savings
Photo by Jennifer Brokaw
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.

Graduate by Hilton New Haven
Downtown New Haven
Save 100% on your flight
Price was $1,149, price is now $867 per person
$867
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (851 reviews)
Great hotel in the niddle of town. A block from the Museum of Art. Park around thr corner..no parking on site.
Reviewed on Aug 11, 2025

Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
Save 100% on your flight
Price was $1,671, price is now $1,222 per person
$1,222
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (51 reviews)
It was a great place. Highly recommend!
Reviewed on Jun 11, 2025

Madison Beach Hotel
Madison Center
Save 100% on your flight
Price was $2,006, price is now $1,470 per person
$1,470
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (305 reviews)
The hotel is beautiful and the grounds are wonderful. The staff was top notch. We will definitely stay again.
Reviewed on Aug 18, 2025

Luxury Apartments by Hyatus at Pierpont
The Hill
Save 100% on your flight
Price was $1,372, price is now $1,035 per person
$1,035
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (19 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.
Reviewed on Jun 27, 2025
Roxbury Hotel Deals

Wyndham Southbury
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Aug 26 to Aug 27
$107 total
Aug 26 - Aug 27
Total includes taxes and fees
8/10 Very Good! (1,009 reviews)
"Great location. Toilets flush slow and run too much. Otherwise very nice!"
Reviewed on Aug 17, 2025

Hilton Garden Inn Shelton
25 Old Stratford Rd, Shelton, CT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $126 total per night from Aug 31 to Sep 1
$126 total
Aug 31 - Sep 1
Total includes taxes and fees
7.8/10 Good! (1,000 reviews)
Brief Stay
"Easy access and comfortable"
Reviewed on Aug 11, 2025

Courtyard by Marriott Waterbury Downtown
63 Grand St, Waterbury, CT
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Sep 2 to Sep 3
$102 total
Sep 2 - Sep 3
Total includes taxes and fees
8.4/10 Very Good! (1,011 reviews)
Just ok.
"Hotel was ok. Locatuon was iffy. Front desk staff were cold. I had to be buzzed in the front entrance and waited a while. Room was ok. One bed great one bed bad. Bathroom was good. AC was loud but good. Expected more from CYM."
Reviewed on Aug 18, 2025
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.
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Bridgewater Hotels
- B&B in Bridgewater
- Condo Rentals in Bridgewater
- Hostels in Bridgewater
- 4 Star Hotels in Bridgewater
- Hotels near Woodbury Ski Area
- Hotels near Institute for American Indian Studies Museum and Research Center
- Hotels near Steep Rock Preserve
- Washington Hotels
- Cabin Rentals in Washington
- Hotels with Restaurants in Washington
- Historic Hotels in Washington
- Hotels with an Indoor Pool in Washington
- Relais & Chateaux Hotels in Washington
- B&B in Washington
- Luxury Hotels in Washington
- 5 Star Hotels in Washington
- Boutique Hotels in Washington
- Romantic Hotels in Washington
- Motels in Washington
- Winery Hotels in Washington
- Honeymoon Resorts & in Washington
- Ski Hotels in Washington
- Resorts & Hotels with Spas in Washington
- Hotels with Tennis Courts in Washington
- Guest Houses in Washington
- Hotels with an Outdoor Pool in Washington
- Hotels & Resorts for Couples in Washington
- Woodbury Hotels
- B&B in Woodbury
- 5 Star Hotels in Woodbury
- Historic Hotels in Woodbury
- Condo Rentals in Woodbury
- 4 Star Hotels in Woodbury
- Family Hotels in Woodbury
- Hotels with Free Breakfast in Woodbury
- Motels in Woodbury
- Lodges in Woodbury
- Ski Hotels in Woodbury
- Hotels with Bars in Woodbury
- Romantic Hotels in Woodbury
- Hotels near Glebe House Museum and The Gertrude Jekyll Garden
- Hotels near Hollow Park
- New Milford Hotels
- Hotels near Pilgrim Mall Shopping Center
- B&B in New Milford
- Cabin Rentals in New Milford
- Hotels with Hot Tubs in New Milford
- Cottages in New Milford
- Cheap Hotels in New Milford
- La Quinta Inn & Suites Hotels in New Milford
- Pet-friendly Hotels in New Milford
- Resorts & Hotels with Spas in New Milford
- Apartments in New Milford
- Best Western Hotels in New Milford
- 5 Star Hotels in New Milford
- Romantic Hotels in New Milford
- RV Parks in New Milford
- 4 Star Hotels in New Milford
- Motels in New Milford
- Hotels with Kitchenettes in New Milford
- Hotels with a Pool in New Milford
- Extended Stay Hotels in New Milford
- Hilton Hotels in New Milford
- 3 Star Hotels in New Milford
- Guest Houses in New Milford
- Hotels with Fireplaces in New Milford
- Luxury Hotels in New Milford
- Historic Hotels in New Milford
- Car rentals near Bridgewater
- Car rentals near Washington
- Airport Van Rental Rental Cars in Washington
- Car rentals near Woodbury
- Car rentals near New Milford
- Enterprise Rental Cars in New Milford
- Car rentals in Sixt Varna Airport, Int. Airport, Arrivals Hall 1
- Hertz Rental Cars in New Milford
- Budget Rental Cars in New Milford
- Van Car Rentals in New Milford
- Payless Rental Cars in New Milford
- Sixt Rental Cars in New Milford
- Avis Rental Cars in New Milford
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.