Eastern Shore Romantic Vacations 2026

Plan, book, travel with confidence
Better together
Save up to $2,000 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 Romantic vacation packages in Eastern Shore

Price found within the past 48 hours. Click for updated prices.

Hyatt Regency Chesapeake Bay

$948

per person

Oct 21 - Oct 25

found 16 hours ago

Roundtrip flight included

New York (JFK) to Salisbury (SBY)

8.8/10 Excellent! (1,006 reviews)

Would definitely return in the near future. My family had fun.

Reviewed on Sep 5, 2026

Inn at Perry Cabin

Downtown St. Michaels

Save 100% on your flight

$2,379

per person

Oct 21 - Oct 25

found 16 hours ago

Roundtrip flight included

New York (JFK) to Salisbury (SBY)

9.6/10 Exceptional! (399 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

View all trips

5* Romantic vacations in Eastern Shore

Price found within the past 48 hours. Click for updated prices.

Inn at Perry Cabin

Downtown St. Michaels

Save 100% on your flight

$2,379

per person

Oct 21 - Oct 25

found 16 hours ago

Roundtrip flight included

New York (JFK) to Salisbury (SBY)

9.6/10 Exceptional! (399 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

View all trips

3 Night Romantic vacations in Eastern Shore

Price found within the past 48 hours. Click for updated prices.

Hyatt Regency Chesapeake Bay

$717

per person

Oct 28 - Oct 31

found 23 hours ago

Roundtrip flight included

San Francisco (SFO) to Salisbury (SBY)

8.8/10 Excellent! (1,006 reviews)

Would definitely return in the near future. My family had fun.

Reviewed on Sep 5, 2026

Inn at Perry Cabin

Downtown St. Michaels

$1,867

per person

Oct 28 - Oct 31

found 23 hours ago

Roundtrip flight included

San Francisco (SFO) to Salisbury (SBY)

9.6/10 Exceptional! (399 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

View all trips

4 Night Romantic vacations in Eastern Shore

Price found within the past 48 hours. Click for updated prices.

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$828

per person

Oct 19 - Oct 23

found 15 hours ago

Roundtrip non-stop flight included

Indianapolis (IND) to Salisbury (SBY)

9/10 Wonderful! (3,843 reviews)

Inn at Perry Cabin

Downtown St. Michaels

Save 100% on your flight

$2,379

per person

Oct 21 - Oct 25

found 16 hours ago

Roundtrip flight included

New York (JFK) to Salisbury (SBY)

9.6/10 Exceptional! (399 reviews)

Hyatt Regency Chesapeake Bay

$948

per person

Oct 21 - Oct 25

found 16 hours ago

Roundtrip flight included

New York (JFK) to Salisbury (SBY)

8.8/10 Excellent! (1,006 reviews)

Would definitely return in the near future. My family had fun.

Reviewed on Sep 5, 2026

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

View all trips

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 $717. 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?