Roxbury Holidays from £741

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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 £796, price is now £741 per person
£741
per person
26 Aug - 30 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to New Haven (HVN)
7/10 Good! (931 reviews)
We got in and had to wait nearly half an hour with small kids for the receptionist to show up to check us in. Then I was bitten by bed bugs.

Reviewed on 9 Jul 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was £925, price is now £808 per person
£808
per person
26 Aug - 30 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to New Haven (HVN)
8/10 Very good! (1,001 reviews)
The room was hot, and AC barely worked.

Reviewed on 10 Jul 2026

Liberty Inn

Liberty Inn

2 out of 5
Price was £786, price is now £761 per person
£761
per person
26 Aug - 30 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to New Haven (HVN)
7.6/10 Good! (657 reviews)
I stayed here with my girlfriend over the July fourth weekend. It was inexpensive. Enjoyable. And the staff was super friendly. The television hadthebtelemundk channel which was awesome because it aired the word cup soccer games. The staff was excellent. Front desk help was superb.

Reviewed on 10 Jul 2026

Spark by Hilton Guilford

Spark by Hilton Guilford

2.5 out of 5
Price was £896, price is now £888 per person
£888
per person
26 Aug - 30 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to New Haven (HVN)
9/10 Wonderful! (150 reviews)
Clean,well kept room. Nice bathroom, comfortable sorroundings.

Reviewed on 10 Jul 2026

Tower Inn And Suites Of Guilford - Madison

Tower Inn And Suites Of Guilford - Madison

2.5 out of 5
Price was £827, price is now £825 per person
£825
per person
26 Aug - 30 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to New Haven (HVN)
7.4/10 Good! (248 reviews)
air conditioning is great. Diner is across the street. Clean rooms. nice size rooms. Plenty of towels.

Reviewed on 14 Jun 2026

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! (52 reviews)
"Great spot. Have stayed here 2x. Once w college friends reunion. Once w fam reunion. Perfect for both."

Reviewed on 3 Jul 2026

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
The price is £94 per night from 23 Jul to 24 Jul
£94
23 Jul - 24 Jul
includes taxes & fees
8/10 Very good! (1,300 reviews)
"This really isn't a fancy hotel but it is very quaint and quite nice to stay."

Reviewed on 10 Jul 2026

Ethan Allen Hotel
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is £75 per night from 2 Aug to 3 Aug
£75
2 Aug - 3 Aug
includes taxes & fees
7.8/10 Good! (1,008 reviews)
"Never in my life that I experienced such horrible customer service. There was a male concierge with a ponytail who did not allow my friends to check in. One of them had their ID, but they weren’t allowed to check in because I wasn’t present. I explained to the concierge over the phone that my father ..."

Reviewed on 8 Jul 2026

Best Western Danbury/Bethel
See all 705 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 £741, 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.

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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. Flight-inclusive packages are ATOL protected.