Roxbury Holidays from £615

Book a Hotel + Flight or Car together to unlock savings

Photo by Jennifer Brokaw

  • Plan, book, travel with confidence

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    Better together

    Save up to £335 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Packages with flights are ATOL protected

Your Roxbury Holiday

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 holiday 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 Centre. Whatever your travel plans or budget, putting together a tailored Roxbury holiday is a cinch with Expedia.

Top Roxbury Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
Price was £692, price is now £615 per person
£615
per person
14 Oct - 19 Oct
found 8 hours ago
Return direct flight included
Birmingham (BHX) to New Haven (HVN)
7/10 Good! (892 reviews)
This was convenient to the highway and to a wedding we were attending at Water's Edge.

Reviewed on 15 Aug 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
Price was £1,602, price is now £1,342 per person
£1,342
per person
14 Oct - 19 Oct
found 8 hours ago
Return direct flight included
Birmingham (BHX) to New Haven (HVN)
9.4/10 Exceptional! (1,004 reviews)
Felt like loyalty. Spotless rooms and bathrooms. Restaurant staff treated us like old friends. We will be back. Thank you so much.

Reviewed on 21 Aug 2025

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was £717, price is now £657 per person
£657
per person
14 Oct - 19 Oct
found 8 hours ago
Return direct flight included
Birmingham (BHX) to New Haven (HVN)
7.8/10 Good! (1,001 reviews)
Good budget friendly hotel

Reviewed on 22 Aug 2025

Roxbury Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Lake Waramaug State Park, Lovers Leap State Park and Woodbury Ski Area

Top hotels in Roxbury

Litchfield County Four Season Country Paradise

Litchfield County Four Season Country Paradise

Roxbury, CT
9.4/10 Exceptional! (46 reviews)
"This property was perfect for our family. We had two littles and 6 adults. The grounds were amazing for the kids to run around on, the game room and children’s bedroom were endlessly entertaining, and the kitchen and dining area were perfect to cook and enjoy our meals. Check-in was seamless and ..."

Reviewed on 18 Aug 2025

Get rates
Litchfield County Four Season Country Paradise
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is £79 per night from 7 Sept to 8 Sept
£79
7 Sept - 8 Sept
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"It was great"

Reviewed on 21 Aug 2025

Wyndham Southbury
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd, Shelton, CT
Fully refundableReserve now, pay when you stay
The price is £94 per night from 31 Aug to 1 Sept
£94
31 Aug - 1 Sept
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Brief Stay
"Easy access and comfortable"

Reviewed on 11 Aug 2025

Hilton Garden Inn Shelton
See all 657 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Roxbury travel package cost?
From as little as £615, you can create your own Roxbury package. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
If I'm not able to travel, can I cancel my Roxbury travel package?
If your travel plans in Roxbury have changed, it's comforting to know that it's possible to cancel your booking. If your booking was made within the last 24 hours, you may be eligible for a refund. If your booking is older than that, your airline, hotel or car rental company may charge a cancellation fee. To learn more, visit our Customer Service Portal.
How do I get a cheap travel package to Roxbury?
It's easy. Just bundle everything together. Hotels, flights and rental cars — combine whatever you need into a Roxbury travel package and save. Score even more discounts when you add extras such as sightseeing tours to your booking. But that's not the only impressive part. You have the freedom to tailor your holiday your way. We offer more than 550 air carriers and 1,000,000 hotels worldwide, so that everyone has a chance to travel and live out those holiday fantasies.
Does Expedia offer Book Now, Pay Later Roxbury holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book your dream getaway without drying up your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna can help. Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.

What are the top hotels in Roxbury?
Book a room at The Litchfield Inn. It's one of this area's most popular hotels. Another top-rated option in Roxbury is Americas Best Value Inn Torrington CT.
How far in advance should I book my Roxbury holiday?
To land rock-bottom prices, book early. Airlines typically begin selling tickets, along with some of the lowest fares, nearly 12 months ahead of time. Hotels, car rental and activities should also be booked early to avoid disappointment. If you're in need of a last-minute getaway to Roxbury, there are always lots of great deals on Expedia. Book something in today!
What does an Expedia Roxbury travel package include?
Flights, rental cars and hotels, or any combination of the three — it's up to you! Whether you're exploring Roxbury on a family road trip or travelling by yourself, there's a bundle to fit your style and budget. Once you've made your booking, why not add on a couple of tours or activities?
What should I know before booking a Roxbury travel package?
Booking all the parts of your holiday together is a great way to save. Combine your flights, car rentals and hotels into a handy package. But hotels aren't your only option. Expedia offers all sorts of properties, including holiday rentals such as beach villas and serviced residences. You've got choices galore!
Can I choose my airline with a Roxbury Expedia travel package?
The choice is all yours! We offer more than 550 partner airlines throughout the world, so you can tailor your Roxbury getaway according to your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.