Discover a selection of 9,000 vacation rentals in Eastern Shore, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $96 per night, and houses and cottages are popular options for a stay in Eastern Shore. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Eastern Shore

What are the top vacation rentals in Eastern Shore?

Luxury villas, secluded treehouses and spacious homes — everyone's ideal escape is different. Whatever you're into, you're sure to find something that tempts you among these top vacation rentals in Eastern Shore:

  • "Gorgeous Direct Ocean Front Condo Overlooking Pool And Beach": If you're looking for somewhere in North Ocean City with 1 bedroom and the comforts of home, this escape is calling your name. Amenities include air conditioning and a toaster.
  • "Water Front Retreat - Sunrise And Sunset Water Views": Located in Chestertown, this sought-after getaway has 3 bedrooms and plenty of handy amenities. Internet services and a fireplace are just a couple you'll find here.

For even more great options, use the search bar at the top of the page to find the perfect Eastern Shore vacation rental for you.

What are the best tiny house vacation rentals in Eastern Shore?

For a memorable experience, book a tiny house rental in Eastern Shore. We warn you though — after you've stayed in a tiny house, the temptation to move into one of these cute-as-a-button digs will be tough to resist!

  • Unwind and reenergize at "Annapolis Waterfront "tiny House" In Garden Setting". Located in Parole, a boat and a blender are just a couple of the amenities you can expect here.
  • Alternatively, make yourself at home at "Tiny House On Ranch Minutes To Beaches". Located in Selbyville, this teensy abode comes with high-speed internet services and a boat.

What are the top-rated vacation rentals for weekend getaways in Eastern Shore?

Waltz out of work on Friday and think no more about deadlines and meetings. Get ready for a few days of good old-fashioned R&R — with a side of adventure — at one of these irresistible weekend getaways in Eastern Shore:

  • "Nancy’s Touch, A Waterfront Paradise" in North East is an excellent choice if you adore the great outdoors. Get out and see the area's natural hot spots, like East Meadow Park and Gunpowder Falls State Park, or try some activities. Hiking and biking and water skiing will keep you busy around these parts.
  • You'll be able to cram a whole lot into your quick break at "Peaceful Cambridge Home On Jenkins Creek". This property is located in Cambridge and is within reach of impressive sights like Adkins Arboretum and Chesapeake Exploration Center. Hiking and biking and golf are some fun experiences also on your doorstep.

Can I find studio apartments for rent in Eastern Shore?

Easy to keep clean and tidy and with everything you need within arm's reach, studio apartments are a terrific option if you're traveling by yourself or with your significant other. If you're after somewhere small and comfortable to call home, consider one of these studio apartments for rent in Eastern Shore:

  • "Gorgeous Direct Ocean Front Condo Overlooking Pool And Beach" in North Ocean City puts you near some of the area's well-known cultural attractions, including Ward Museum of Wildfowl Art and Bishop's Stock Fine Art, Craft & Wine. A nearby bay and free WiFi are a couple of handy amenities here.
  • Located in Ocean City, "Commanding View From Direct Oceanfront Condo" is another terrific base for your adventure. When you've finished checking out hot spots like Ward Museum of Wildfowl Art and Bishop's Stock Fine Art, Craft & Wine, make use of an iron and ironing board and a living room back at your apartment.

Can I find short term rentals in Eastern Shore?

Short-term rentals come in all shapes, sizes and budgets in Eastern Shore. Whether you're organizing a quick trip with the family or a few nights with your partner, we'll help you find the ideal retreat. Here are some popular options:

  • "Nancy’s Touch, A Waterfront Paradise" in North East will put out the welcome mat for you. Spend your vacation doing little else except chilling here or get out and explore. Elk Neck State Park and Bohemia Vista Marina are among the top things to check out nearby.
  • Come for the home comforts of "Peaceful Cambridge Home On Jenkins Creek", stay for the intriguing sights scattered around it. This getaway in Cambridge puts you close to Harriet Tubman Museum and Educational Center, Bay Country Shop and other highlights.

What are the best romantic weekend getaways in Eastern Shore?

A romantic weekend getaway in Eastern Shore is sure to reignite your passion. Light some scented candles, take your love by the hand and get set to send sparks flying at one of these vacation rentals:

  • "Gorgeous Direct Ocean Front Condo Overlooking Pool And Beach" in North Ocean City will convince you to make romantic weekends away a regular thing. This retreat is full of nice touches, including a nearby bay and a fireplace.
  • Alternatively, treat you and your love to an amorous weekend break at "Water Front Retreat - Sunrise And Sunset Water Views". Located in Chestertown, it offers winery tours, a fireplace and more.

Are there mansions for rent in Eastern Shore?

Whether you're in search of somewhere luxurious and spacious for a family getaway, a reunion with friends or a special event, we've got mansions for rent in Eastern Shore to suit everyone. Here are a couple that'll knock your socks off:

  • Spend a few nights or longer enjoying the high life at "Chesapeake Mansion - New Pool/12" in Sherwood. A swimming pool and a firepit are just a couple of the premium amenities waiting for you here.
  • "Kingsbay Mansion Bayhouse" is another fancy option that's hard to overlook. It's located in Marion Station and comes with plenty of highlights your guests will love, including a swimming pool and a garden.

What are the best large group vacation rentals in Eastern Shore?

If you're thinking about taking that special trip away, don't go by yourself; take the whole gang. It's always more fun to share the experience with the people you love. These vacation rentals in Eastern Shore are perfect for larger groups:

  • "5 - 6br, 5ba And Boat Slip In Bayside Retreat With Community Pools": This getaway is a terrific choice for larger groups planning a visit to North Ocean City. It has 6 bedrooms and lots of great amenities, including a swimming pool and a nearby waterfront.
  • "240' Private Beachfront @kent Island Love Point": Located in Stevensville, this spacious stay has 5 bedrooms and is another favorite for a get-together with the family. There's a whole lot to keep guests content and comfortable, including a firepit and a kitchen.

Are there large vacation rentals that sleep 30 or more in Eastern Shore?

Whether you're planning a vacation with a large group of friends, a big birthday bash or even a wedding, we'll help you find the perfect space. Round up your best buds and look at these large vacation rentals in Eastern Shore:

  • "Large Group And Families - To 30 With 8 To 12 Bedrooms": This vacation rental in Ocean City has 12 bedrooms and can accommodate up to 30 people. As well as ample space, it comes with a water park and a kitchen.
  • "5eastern Shore/cambridge 250 Acres On Chesapeake Bay Vacation": Situated in Mid-Atlantic, this spacious option features a garden and a firepit. It has 12 bedrooms and can comfortably accommodate up to 40 guests.

What are the best houses for rent with a pool in Eastern Shore?

You'll have your choice of houses with a pool in Eastern Shore, so pull on your swimsuit and get ready to spend your days splashing about. Here are two top options to get you inspired:

  • Parents, kids, uncles, aunts — everyone will enjoy the pool at "Premier St. Michaels Cottage - T. Blades House". Take the family on a trip to this St. Michaels rental house which also comes with a swimming pool and free toiletries.
  • "Dune Residence Glowe House Luisa To The Beach 200 M" in Glowe is another popular pick. There's a whole lot to love about this property apart from its pool, such as towels and a pool table.