Title: Roxbury Vacation Packages 2026 from $396 | Expedia.com [Roxbury Travel Guide](https://expedia.com/Roxbury.dx153612)[Hotels in Roxbury](https://expedia.com/Roxbury-Hotels.d153612.Travel-Guide-Hotels)[Vacation Rentals in Roxbury](https://expedia.com/Roxbury-Vacation-Rentals.d153612.Travel-Guide-VacationRentals)[Flights to Roxbury](https://expedia.com/Cheap-Flights-To-Roxbury.d153612.Travel-Guide-Flights)[Car Rentals in Roxbury](https://expedia.com/Car-Rentals-In-Roxbury.d153612.Car-Rental-Guide) ![](https://images.trvl-media.com/place/153612/17e8b0b2-bf51-4bdc-95e1-af5aaf3f5198.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Roxbury Vacations from $396 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## 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](https://www.expedia.com/Glebe-House-Museum-And-The-Gertrude-Jekyll-Garden-Woodbury.d553248621532664756.Vacation-Attraction), [Woodbury Ski Area](https://www.expedia.com/Woodbury-Ski-Area-Woodbury.d6089861.Vacation-Attraction) and [Pilgrim Mall Shopping Center](https://www.expedia.com/Pilgrim-Mall-Shopping-Center-Woodbury.d553248621563220790.Vacation-Attraction). 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. ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/b7b5473a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni New Haven Hotel at Yale Downtown New Haven $396 per person Apr 24 - Apr 26 found 17 hours ago Roundtrip flight included Raleigh (RDU) to New Haven (HVN) 8.6/10 Excellent! (1,004 reviews) Will always book here it was beautiful and staff was great love it 10/10 Reviewed on Mar 7, 2026 ![Graduate by Hilton New Haven](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/d3190acf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Graduate by Hilton New Haven Downtown New Haven Save 100% on your flight $1,029 per person May 28 - May 31 found 18 hours ago Roundtrip flight included Tampa (TPA) to New Haven (HVN) 9.2/10 Wonderful! (958 reviews) Groovy, fun, comfortable hotel in a great location. Reviewed on Mar 3, 2026 ![Hyatus Luxury Residences City Crossing](https://images.trvl-media.com/lodging/77000000/76890000/76889000/76888939/2e7a06d9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatus Luxury Residences City Crossing The Hill Save 100% on your flight $1,446 per person May 17 - May 19 found 13 hours ago Roundtrip flight included Orlando (ORL) to New Haven (HVN) 9.2/10 Wonderful! (29 reviews) Communication and ease Reviewed on Mar 8, 2026 ![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ec18076_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Madison Beach Hotel Madison Center $818 per person May 17 - May 19 found 13 hours ago Roundtrip flight included Orlando (ORL) to New Haven (HVN) 9.4/10 Exceptional! (347 reviews) beautiful room and views Reviewed on Dec 13, 2025 ![Luxury Furnished Apartments by Hyatus Downtown at Yale](https://images.trvl-media.com/lodging/58000000/57250000/57240500/57240415/695af8be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Luxury Furnished Apartments by Hyatus Downtown at Yale The Hill Save 100% on your flight $1,459 per person May 17 - May 19 found 13 hours ago Roundtrip flight included Orlando (ORL) to New Haven (HVN) 9.6/10 Exceptional! (64 reviews) Everything here has been excellent. I am a travel nurse and they have really helped to make my trip here the best. Reviewed on Feb 27, 2026 Don't see what you're looking for? See all available trips from Columbus to Roxbury [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-15/2026-04-22/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=BDR&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_153612) ## Roxbury Hotel Deals ![Best Western Danbury/Bethel](https://images.trvl-media.com/lodging/1000000/10000/4900/4841/b09513bc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Danbury/Bethel 11 Stony Hill Road Bethel CT Fully refundableReserve now, pay when you stay $75 nightly $86 total Apr 5 - Apr 6 Total with taxes and fees 7.8/10 Good! (1,000 reviews) Average place to stay. Clean & quiet room on 1st floor. Staff at morning breakfast were very friendly & helpful. Reviewed on Mar 10, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=4841&PinnedHotelID=4841&HadPinnedHotel=true®ionId=153612) ![Hotel Zero Degrees Danbury](https://images.trvl-media.com/lodging/17000000/16270000/16263900/16263812/8667a2b4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Zero Degrees Danbury 15 Milestone Road Danbury CT Fully refundableReserve now, pay when you stay $161 nightly $185 total Mar 16 - Mar 17 Total with taxes and fees 9.2/10 Wonderful! (1,005 reviews) I put a note in my RSVP that I would arrive early and need to check in to get ready for a party we had at 2pm. At check in we waiting about 15 min until the one employee showed up to check us in. We were really annoyed at this point but he checked us in and gave us keys right away, well before check ... Reviewed on Mar 12, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%2F2026&selected=16263812&PinnedHotelID=16263812&HadPinnedHotel=true®ionId=153612) ![Hyatt House Shelton](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/a12e56fc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt House Shelton 830 Bridgeport Ave Shelton CT Fully refundableReserve now, pay when you stay $115 nightly $132 total Mar 22 - Mar 23 Total with taxes and fees 8.4/10 Very Good! (1,008 reviews) Clean room, plenty of amenities Reviewed on Mar 13, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=3482162&PinnedHotelID=3482162&HadPinnedHotel=true®ionId=153612) [See all 677 properties in Roxbury](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F16%2F2026&endDate=3%2F17%2F2026®ionId=153612) 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](https://www.expedia.com/Lake-Waramaug-State-Park-Kent.d553248621561735287.Vacation-Attraction), [Lovers Leap State Park](https://www.expedia.com/Lovers-Leap-State-Park-Danbury.d637209878835023872.Vacation-Attraction) and [Woodbury Ski Area](https://www.expedia.com/Woodbury-Ski-Area-Woodbury.d6089861.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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[](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Roxbury vacation package cost? ### What are the cheapest months to go to Roxbury? ### How many days is enough for Roxbury? ### How to find the best Roxbury package deals? ### Is it cheaper to book a Roxbury vacation as a package? ### When to book a vacation package to Roxbury? ### Does Expedia offer Book Now, Pay Later Roxbury vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - 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