Title: Windsor Vacation Packages 2026 | Expedia.com [Hotels in Windsor](https://expedia.com/Windsor-Hotels.d3000001822.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d3000001822.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d3000001822.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d3000001822.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor Vacations ## 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 ## Windsor Hotel Deals ![Brydone Hotel Oamaru](https://images.trvl-media.com/lodging/1000000/400000/393400/393302/5484cd94_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Brydone Hotel Oamaru 115 Thames Street Oamaru $79 nightly $92 total Mar 30 - Mar 31 Total with taxes and fees 8.6/10 Excellent! (595 reviews) It’s good overall accommodation Reviewed on Mar 13, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F30%2F2026&endDate=3%2F31%2F2026&selected=393302&PinnedHotelID=393302&HadPinnedHotel=true®ionId=3000001822) ![Poshtel](https://images.trvl-media.com/lodging/31000000/30990000/30982700/30982620/3a4c4236_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Poshtel 126 Thames Street Oamaru Otago $112 nightly $130 total Mar 27 - Mar 28 Total with taxes and fees 9.6/10 Exceptional! (389 reviews) Small but comfortable room. Good amenities and great location with the historical center, restaurants and shopping close by. Reviewed on Mar 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F27%2F2026&endDate=3%2F28%2F2026&selected=30982620&PinnedHotelID=30982620&HadPinnedHotel=true®ionId=3000001822) ![Criterion Boutique Hotel](https://images.trvl-media.com/lodging/120000000/119520000/119516300/119516212/5e727648_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Criterion Boutique Hotel 3 Tyne St Oamaru Otago Region Fully refundableReserve now, pay when you stay $55 nightly $63 total Mar 25 - Mar 26 Total with taxes and fees 7/10 Good! (36 reviews) Rooms need a good clean . No hand towels for use in shared bathroom. Garbage upstairs was not taken out we were their two days. Needs a bit of modernizing . Has charm and history could be a real busy little boutique . All the doors and windows need some oil . Might help prevent guests from being ... Reviewed on Mar 21, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F25%2F2026&endDate=3%2F26%2F2026&selected=119516212&PinnedHotelID=119516212&HadPinnedHotel=true®ionId=3000001822) [See all 69 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F24%2F2026&endDate=3%2F25%2F2026®ionId=3000001822) 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 Windsor Vacation Packages ## Windsor Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | New Zealand dollars | | Max Temp Winter | 50ºF | | Max Temp Summer | 60ºF | | Top Sights | [Oamaru Gardens](https://www.expedia.com/Oamaru-Gardens-Oamaru.d6112986.Vacation-Attraction), [Janet Frame House](https://www.expedia.com/Janet-Frame-House-Oamaru.d6112988.Vacation-Attraction) and [Totara Estate](https://www.expedia.com/Totara-Estate-Reidston.d6112994.Vacation-Attraction) | ## More vacations you might like 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Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app