Eastern Shore Romantic Vacations
Book a Hotel + Flight or Car together to unlock savings
Top Romantic vacation packages in Eastern Shore
Price found within the past 48 hours. Click for updated prices.
- Kent Island Resort
Sep 5 - Sep 7Kent Island Resort + Flight
Stevensville2 nights3.5 star property9.2/10 - Wonderful (165 reviews)"We booked Kent Island Resort for our anniversary because it looked beautiful online. We even paid extra for a balcony room because we pictured ourselves ending the night sitting outside with a glass of wine, enjoying the water. The grounds? Beautiful. Seriously. Whoever takes care of the landscaping deserves a raise. The room? A completely different story. Kent Island Resort advertises itself as a luxury boutique resort. Luxury isn't just beautiful landscaping and a nice website. Luxury means..."Reviewed July 20, 2026Roundtrip • Miami (MIA) - Baltimore (BWI)MIA - DCA • Nonstop BWI - MIA • Nonstop$530$415found 11 hours agoper traveler - Grand Hotel Ocean City Oceanfront
Aug 24 - Aug 27Grand Hotel Ocean City Oceanfront + Flight
Downtown Ocean City3 nights3.0 star property9.0/10 - Wonderful (3,705 reviews)"1. Upon arrival at 1:30 am the desk attendant was very high. He booked us in the incorrect room leading to housekeeping and security banging on the door at 7:00 am the next morning asking why we were in said room. 2. After checking in at 1:30 am I proceeded to the bar for a wind down and attempted to use the in lobby ATM. To my surprise it did not work and lock my bank card. When I asked the highly intoxicated desk personnel he was no help when he suggested that I “just hang out” until..."Reviewed July 22, 2026Roundtrip • Boston (BOS) - Salisbury (SBY)BOS - SBY • 1 stop SBY - BOS • 1 stop$1,103$862found 1 day agoper traveler - Princess Royale Oceanfront Resort
Sep 24 - Sep 27Princess Royale Oceanfront Resort + Flight
North Ocean City3 nights3.0 star property8.8/10 - Excellent (2,536 reviews)Roundtrip • Boston (BOS) - Salisbury (SBY)BOS - SBY • 1 stop SBY - BOS • 1 stop$1,635$1,362found 1 day agoper traveler - Holiday Inn Ocean City by IHG
Sep 24 - Sep 27Holiday Inn Ocean City by IHG + Flight
North Ocean City3 nights3.0 star property8.6/10 - Excellent (1,001 reviews)"Great"Reviewed July 23, 2026Roundtrip • Boston (BOS) - Salisbury (SBY)BOS - SBY • 1 stop SBY - BOS • 1 stop$1,730$1,593found 1 day agoper traveler - Carousel Resort Hotel & Condominiums
Sep 24 - Sep 27Carousel Resort Hotel & Condominiums + Flight
North Ocean City3 nights3.0 star property7.8/10 - Good (1,412 reviews)"Hotel was great! The only downside was the air did not work the greatest and they had a box fan in the closet to assist."Reviewed July 22, 2026Roundtrip • Boston (BOS) - Salisbury (SBY)BOS - SBY • 1 stop SBY - BOS • 1 stop$1,295$1,198found 1 day agoper traveler
Discover the most popular places to visit in Eastern Shore
Top Romantic Eastern Shore Hotels
Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & Suites2.5 star property
13.9 mi from Eastern Shore
9.2 out of 10, Wonderful, (1,003 reviews)
9.2/10
Wonderful
(1,003 reviews)
$139 nightly
The price is $153
$153 total
Jul 26 - Jul 27
Total with taxes and fees
Holiday Inn Express Easton by IHG
Holiday Inn Express Easton by IHG3.0 star property
13.8 mi from Eastern Shore
9.0 out of 10, Wonderful, (621 reviews)
9.0/10
Wonderful
(621 reviews)
$149 nightly
The price is $164
$164 total
Jul 26 - Jul 27
Total with taxes and fees
Hampton Inn & Suites Salisbury/Fruitland
Hampton Inn & Suites Salisbury/Fruitland2.5 star property
26.6 mi from Eastern Shore
9.0 out of 10, Wonderful, (1,000 reviews)
9.0/10
Wonderful
(1,000 reviews)
"Everything was awesome. Pool, breakfast and room. Toilet stopped working though but front desk fixed it for us quickly!"
$106 nightly
The price is $118
$118 total
Aug 16 - Aug 17
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
Fairfield Inn & Suites by Marriott Easton3.0 star property
14.3 mi from Eastern Shore
9.6 out of 10, Exceptional, (381 reviews)
9.6/10
Exceptional
(381 reviews)
"Just went in to get some sleep. Staff booked me far from noisy areas. I was able to sleep peacefully all night"
$135 nightly
The price is $149
$149 total
Aug 2 - Aug 3
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Newark - Elkton
La Quinta Inn & Suites by Wyndham Newark - Elkton3.0 star property
67.6 mi from Eastern Shore
9.0 out of 10, Wonderful, (1,000 reviews)
9.0/10
Wonderful
(1,000 reviews)
$93 nightly
The price is $104
$104 total
Aug 9 - Aug 10
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina3.0 star property
29.7 mi from Eastern Shore
9.4 out of 10, Exceptional, (793 reviews)
9.4/10
Exceptional
(793 reviews)
"ROOM WAS VERY CLEAN. WATER PRESSURE WAS THE BEST I'VE EXPERIENCED! PROPERTY WAS WELL MAINTAINED AND VERY CONVENIENT TO RESTAURANTS,"
$169 nightly
The price is $188
$188 total
Jul 30 - Jul 31
Total with taxes and fees
8.6 out of 10, Excellent, (615 reviews)
8.6/10
Excellent
(615 reviews)
$138 nightly
The price is $153
$153 total
Aug 2 - Aug 3
Total with taxes and fees
Comfort Inn & Suites Cambridge
Comfort Inn & Suites Cambridge2.5 star property
12 mi from Eastern Shore
8.2 out of 10, Very Good, (864 reviews)
8.2/10
Very Good
(864 reviews)
$116 nightly
The price is $129
$129 total
Aug 17 - Aug 18
Total with taxes and fees
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.
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.
How to find a romantic Eastern Shore vacation
How can I find the best Eastern Shore vacation packages for couples?
To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.
How can I find cheap Eastern Shore romantic packages for two?
For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.
How can I plan a great romantic trip to Eastern Shore?
Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.
How much is a trip for two to Eastern Shore?
Put a price on love with stunning deals for duos starting at just $415. Prices and availability are subject to change. Additional terms may apply.
Can I book Eastern Shore spa packages for couples?
Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.
How can I book romantic weekend getaway packages in Eastern Shore?
To book a loved-up break in Eastern Shore, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).
Can I book a romantic trip to Eastern Shore with free cancellation and/or flexible dates?
The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.
Why should I book my Eastern Shore romantic holiday with Expedia?
If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?