What are the top rated Cottage Rentals in Maryland?

There are a lot of options in Maryland. If you plan on staying in the Maryland area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Maryland: <a href="/property/annapolis-waterfront-tiny-house-in-garden-setting/HA-3211152603" class="class="static-page-link"">Annapolis waterfront &#34;tiny house&#34; in garden setting</a> <a href="/property/potomac-river-getaway-at-mckays-beach/HA-3211570197" class="class="static-page-link"">Potomac River Getaway at McKays Beach</a> <a href="/property/st-michael-s-premier-in-town-rental-with-heated-pool/HA-121287681" class="class="static-page-link"">St. Michael&#39;s Premier In-Town Rental with heated pool.</a> <a href="/property/blissful-retreat-in-rock-hall/HA-3211606636" class="class="static-page-link"">Blissful Retreat In Rock Hall</a> <a href="/property/life-is-better-at-the-river-cozy-waterfront-cottage/HA-3211596624" class="class="static-page-link"">Life is better at the RIVER!-Cozy waterfront cottage</a> <a href="/property/charming-waterfront-cottage-outside-st-michaels-close-to-the-oaks/HA-321558222" class="class="static-page-link"">Charming Waterfront Cottage Outside St. Michaels Close to the Oaks</a> <a href="/property/chesapeake-bay-cottage/HA-3211869065" class="class="static-page-link"">Chesapeake Bay Cottage</a> <a href="/property/stone-riverside-cottage-is-just-a-few-steps-from-the-sassafras-rivers-edge/HA-3213422043" class="class="static-page-link"">STONE RIVERSIDE COTTAGE is just a few steps from the SASSAFRAS RIVERS edge</a> <a href="/property/truly-waterfront-cottage/HA-3211995833" class="class="static-page-link"">Truly Waterfront Cottage</a> <a href="/property/the-cove-on-the-waterfront/HA-3212826658" class="class="static-page-link"">The Cove On The Waterfront</a>

How much does it cost to rent a cottage in Maryland?

The average cost for a cottage rental in Maryland is $337 per night. Trippymates has a wide list of great cottages near Maryland that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Maryland that allow pets?

Yes, here are the top cottage rentals in Maryland that allow you to bring your pet: Eastern Shore beach cottage get-away Cozy Cottage with Yard Less Than 2 Mi to Choptank River Moonlight Ridge by Taylor Made Deep Creek Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch <a href="/all/usa/maryland" class="class="static-page-link"">See all pet-friendly vacation rentals in Maryland on Trippymates</a>

Do you have any rental cottages in Maryland that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Maryland to find one that works for you.

Are there quality cottages in Maryland that have indoor swimming pools?

As of 2025, the data from Trippymates shows that there are Over 456 private swimming pools or cottages with indoor pools in the Maryland area along with other great amenities.

Maryland Cottage Rentals By Owner

From US $312

10.0 (138 Reviews)

Cottage

Eastern Shore beach cottage get-away

Air Conditioner
Parking
Pet Friendly

Maryland Cottage Rentals & Holiday Homes

Find the best cottages in Maryland - We found 456 exact matches

When do you want to travel?