Kent Island Romantic Holidays

Book a Romantic Hotel + Flight or Car together to unlock savings

Photo by Jennifer Crim
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How to find a romantic Kent Island holiday

How can I find the best Kent Island vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Kent Island. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Kent Island romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Kent Island that start from . Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Kent Island romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Kent Island?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Kent Island?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Kent Island that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Kent Island with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Kent Island romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

Top Romantic Kent Island Hotels

Kent Island Resort
Kent Island Resort
3.5 out of 5
500 Kent Manor Dr, Stevensville, MD
  • 29 min walk from Matapeake State Park
Stay at this golf hotel in Stevensville. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.2/10 Wonderful! (103 reviews)

Couples like: couples dining, champagne service

Travellers say...
"It was an amazing stay overall. Unfortunately the pool was drained and the bed was broken and very lose."

Reviewed on 13 Jun 2025

Kent Island Resort
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Stevensville, MD
  • 7 min drive from Matapeake State Park
Stay at this beach holiday home in Stevensville. Enjoy free Wi-Fi, a beach locale and breakfast (surcharge). Popular attractions Matapeake State Park and Romancoke ...

Couples like: hot tub, on the beach, fireplace

Family Reunion
"We were on Kent Island for a family reunion. This property comfortably accommodated our group of 6 adults and 4 children ages 10-16 (3 families). The bedrooms were large enough and spread out enough to allow for privacy and quiet spots. The volleyball court was a big hit with everyone. There were ..."

Reviewed on 20 Aug 2024

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4 out of 5
180 Pier One Road, Stevensville, MD
  • 4 min drive from Matapeake State Park
Stay at this 4-star spa hotel in Stevensville. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (398 reviews)

Couples like: full-service spa, bar

Travellers say...
"Staff was very polite and friendly."

Reviewed on 28 Jun 2025

The Inn at Chesapeake Bay Beach Club
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.

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.