Title: Eastern Shore Luxury Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/6286116/d4aad82a-b6ac-4cb6-992a-8f51658bb937.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Eastern Shore Luxury Vacations ## Book a Luxury 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 ## Top Luxury vacation packages in Eastern Shore Price found within the past 48 hours. Click for updated prices. ![Hilton Ocean City Oceanfront Suites](https://images.trvl-media.com/lodging/1000000/30000/27700/27630/502613d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Ocean City Oceanfront Suites Midtown Ocean City $523 per person Mar 31 - Apr 4 found 1 day ago Roundtrip flight included Orlando (MCO) to Salisbury (SBY) 8.8/10 Excellent! (1,309 reviews) Location, cleanliness, and spacious rooms were the best. Ocean view was amazing fron the suit. Reviewed on Feb 17, 2026 ![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn at Perry Cabin Downtown St. Michaels Save 100% on your flight $668 per person Apr 3 - Apr 5 found 3 hours ago Roundtrip flight included New York (NYC) to Salisbury (SBY) 9.6/10 Exceptional! (369 reviews) Friendly and attentive staff, good cleaning services Reviewed on Oct 26, 2025 Don't see what you're looking for? See all available trips from Columbus to Eastern Shore [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-24/2026-03-31/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ILG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury vacations in Eastern Shore Price found within the past 48 hours. Click for updated prices. ![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn at Perry Cabin Downtown St. Michaels Save 100% on your flight $668 per person Apr 3 - Apr 5 found 3 hours ago Roundtrip flight included New York (NYC) to Salisbury (SBY) 9.6/10 Exceptional! (369 reviews) Friendly and attentive staff, good cleaning services Reviewed on Oct 26, 2025 Don't see what you're looking for? See all available trips from Columbus to Eastern Shore [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-24/2026-03-31/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ILG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury vacations in Eastern Shore Price found within the past 48 hours. Click for updated prices. ![Hilton Ocean City Oceanfront Suites](https://images.trvl-media.com/lodging/1000000/30000/27700/27630/502613d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Ocean City Oceanfront Suites Midtown Ocean City $751 per person Apr 4 - Apr 7 found 12 hours ago Roundtrip non-stop flight included Bangor (BGR) to Salisbury (SBY) 8.8/10 Excellent! (1,309 reviews) Location, cleanliness, and spacious rooms were the best. Ocean view was amazing fron the suit. Reviewed on Feb 17, 2026 Don't see what you're looking for? See all available trips from Columbus to Eastern Shore [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-24/2026-03-31/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ILG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury vacations in Eastern Shore Price found within the past 48 hours. Click for updated prices. ![Oceanic Motel](https://images.trvl-media.com/lodging/2000000/1570000/1565700/1565652/57c5109d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceanic Motel Downtown Ocean City $814 per person May 14 - May 18 found 1 day ago Roundtrip non-stop flight included Memphis (MEM) to Salisbury (SBY) 7/10 Good! (759 reviews) This is one of the oldest hotels left in Ocean City. It's an aging classy lady that we all know and love. The room was Bayside, small queen but it was meticulous and adequate. The staff was extremely friendly and helpful. But we came for the stunning views and the small private beach where you can relax or even fish or just sit for hours and watch the boats pass through the inlet. I'm sure during the summer it's full of families, however in October it was quiet and pleasant. All in all I was pleasantly surprised at a hotel I've passed by for 50 years and we're definitely stay again Reviewed on Oct 19, 2025 ![Princess Royale Oceanfront Resort](https://images.trvl-media.com/lodging/1000000/30000/22000/21981/b0fe2b94_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Princess Royale Oceanfront Resort North Ocean City $957 per person May 14 - May 18 found 1 day ago Roundtrip non-stop flight included Memphis (MEM) to Salisbury (SBY) 8.6/10 Excellent! (2,269 reviews) Spacious suite, very clean, will be back when it gets warm to enjoy the waterfront restaurant and beach access. Reviewed on Feb 22, 2026 ![Courtyard Ocean City Oceanfront](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/948c4eac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard Ocean City Oceanfront Downtown Ocean City $1,048 per person May 14 - May 18 found 1 day ago Roundtrip non-stop flight included Memphis (MEM) to Salisbury (SBY) 9.2/10 Wonderful! (995 reviews) clean hotel/room. Staff was amazing Reviewed on Jan 13, 2026 Don't see what you're looking for? See all available trips from Columbus to Eastern Shore [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-24/2026-03-31/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ILG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All you need to know about luxury vacations in Eastern Shore #### What can I expect from a luxury Eastern Shore vacation? Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Eastern Shore vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. #### How can I find all-inclusive luxury vacation packages in Eastern Shore? By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5\* filter to find truly sensational stays. You barely need to lift a finger. #### Can I book a cheap Eastern Shore luxury vacation? Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $523\. Prices and availability are subject to change. Additional terms may apply. #### How can I book a luxury family vacation in Eastern Shore? Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. #### Can I book a package in Eastern Shore with a luxury vacation home? A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package. #### How can I find the best luxury vacation deals in Eastern Shore? Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months. #### Can I book a luxury holiday in Eastern Shore with free cancellation and/or flexible dates? Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. #### Why should I book my luxury trip to Eastern Shore with Expedia? A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind. ## Top Luxury Eastern Shore Hotels ![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Inn at Perry Cabin 308 Watkins Ln St. Michaels MD - 2 hours drive from Ocean City Boardwalk Be treated to luxurious accommodations at Inn at Perry Cabin, where you can enjoy amenities like 24-hour room service, plush bedding, and more. Deluxe amenities ... 9.6/10 Exceptional! (374 reviews) We had a great stay, hotel was very clean and food was great Reviewed on Jan 3, 2026 [](https://expedia.com/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![Inn at 202 Dover](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/be8a1621_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Inn at 202 Dover 202 East Dover Street Easton MD - 2 hours drive from Ocean City Boardwalk Pamper yourself with an extravagant stay at Inn at 202 Dover, where you'll find jetted bathtubs and pillowtop beds. Deluxe amenities at this inn include a restaurant, ... [](https://expedia.com/Easton-Hotels-Inn-At-202-Dover.h5308723.Hotel-Information) ![Lighthouse Club Hotel](https://images.trvl-media.com/lodging/11000000/10420000/10418900/10418825/7f2da0de_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lighthouse Club Hotel 200 56th Street Ocean City MD - 8 min drive from Ocean City Boardwalk Pamper yourself with a luxury stay at Lighthouse Club Hotel, where you can enjoy amenities like massage services, Frette Italian sheets, and more. Notable amenities ... [](https://expedia.com/Ocean-City-Hotels-Lighthouse-Club-Hotel.h10418825.Hotel-Information) [See all 7,471 properties in Eastern Shore](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6025644) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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](https://expedia.com/Eastern-Shore-Vacation-Rentals.d6025644.Travel-Guide-VacationRentals)[ Car Rentals in Eastern Shore ](https://expedia.com/Car-Rentals-In-Eastern-Shore.d6025644.Car-Rental-Guide)[ Eastern Shore Vacations ](https://expedia.com/Eastern-Shore.d6025644.Destination-Travel-Guides)[ Things to do in Eastern Shore ](https://expedia.com/Things-To-Do-In-Eastern-Shore.d6025644.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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