Deals on vacations and trips to Roxbury

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Roxbury flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $584, price is now $499 per person
$499
per person
Dec 18 - Dec 20
just found
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,149, price is now $1,193 per person
$1,193
per person
Dec 27 - Dec 30
found 2 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Las Flores Villa

Las Flores Villa

5 out of 5
Save 100% on your flight
Price was $5,578, price is now $3,999 per person
$3,999
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This vacation home features an outdoor pool and a hot tub. Families will appreciate the playground and onsite laundry facilities. Enjoy the sauna and perks like free self parking.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $745, price is now $610 per person
$610
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $751, price is now $660 per person
$660
per person
Dec 18 - Dec 20
just found
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.

Top Roxbury hotels deals

Litchfield County Four Season Country Paradise

Litchfield County Four Season Country Paradise

Roxbury CT
Get rates
This vacation home features an outdoor pool and a gym. Families will appreciate the arcade/game room and barbecue grills. Enjoy the hot tub and conveniences like a garden and laundry facilities.
Pool
Hot Tub
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $119 total per night
$119 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free train station pick-up. Enjoy the seasonal outdoor pool and perks like free self parking.
Pool
Pet friendly
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $113 total per night
$113 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 2 conference rooms, along with the business center. Multilingual staff can provide around-the-clock assistance and free newspapers are on offer.
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St Waterbury CT
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $114 total per night
$114 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a 24-hour business center, and a coffee shop are also offered.
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
522 Heritage Road Southbury CT
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $140 total per night
$140 total
Nov 3 - Nov 4
Total with taxes and fees
A golf course and an indoor pool are featured at this smoke-free hotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and unwind at the bar/lounge and poolside bar.
Pool
Hot Tub
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road Southbury CT
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $100 total per night
$100 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking and a free area shuttle.
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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.

Frequently asked questions

How much are vacation packages to Roxbury?
$499 is all you'll need for an amazing break in Roxbury. Bundle your flights and hotel into a vacation package with Travelocity and see the savings start to grow. With such good prices, traveling has never been so accessible.
Where can I get the best vacation package deals for Roxbury?
Snapping up a great package deal to Roxbury couldn't be easier with Travelocity. With around 400 air carriers and 1,000,000 worldwide properties, the choice is yours when selecting your flights and hotels.
Why should I book my Roxbury vacation package with Travelocity?
The three S's — savings, support and a stress-free booking — are just the tip of the iceberg. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on round-the-clock support. With the Travelocity Price Match Guarantee, you know you'll always get the best deal available.
Can I save money on my Roxbury car rental if I bundle it with hotels and flights?
Combining your car, hotel and flight into a Roxbury vacation package is an easy way to score the best deal. Plus, having your own wheels gives you the freedom to make your way to all the landmarks you can't wait to explore. Situated 65 mi from Roxbury, Times Square is one attraction that should feature on your itinerary. Turn up the tunes and make a day trip of it.
Which airport is best for Roxbury?
LaGuardia Airport (LGA) is 60 mi from the city center and is the starting point for many fun adventures. Alternatively, Bradley Intl. Airport (BDL) is 40 mi away from central Roxbury and MacArthur Airport (ISP) is 55 mi away from central Roxbury.
Where should I stay when visiting Roxbury?
The Classic Roxbury Home w/ Picturesque Backyard! is the number one choice of many visitors. Book soon before it's too late.

Photos of local treasures

Browse Roxbury vacation photos for more inspiration

A waterfall cascading over rocks into a clear river surrounded by lush greenery and trees.
A stone structure in a forested area with autumn foliage.
A rural landscape with a road, a barn, and a field.