Eastern Shore Vacation Rentals from CA $84: Short-Term Rentals for 2026

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Our top choices for Eastern Shore vacation rentals

A row of mobile homes with a one-way sign, a covered porch, and a street sign indicating 'Shore Point Lane'.

1. Shore Point Cottages

Berlin

Kelly

CA $165 total

includes taxes & fees

Nov 10 - Nov 11

A balcony with a view of a river, greenery, and distant buildings.

2. Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Midtown Ocean City

cara

CA $144 total

includes taxes & fees

Nov 28 - Nov 29

A room with a large bed, multiple windows, and a ceiling fan.

3. Salisbury Riverfront Lofts

Salisbury

Carmen

CA $355 total

includes taxes & fees

Nov 8 - Nov 9

A living room with two grey sofas, a coffee table, and a ceiling fan.

4. Cambridge Apt in Walkable Neighborhood

Cambridge

LOIS

CA $451 total

includes taxes & fees

Nov 9 - Nov 10

A deck with a view of a marina, including boats and docks.

5. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

CA $363 total

includes taxes & fees

Nov 12 - Nov 13

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

6. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

CA $210 total

includes taxes & fees

Nov 9 - Nov 10

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

7. Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Quinton

CA $163 total

includes taxes & fees

Nov 9 - Nov 10

A living room with a sofa, a coffee table, a chair, and a dining table. There are two windows with curtains, a lamp, and a painting on the wall.

8. On Main Street - Apartment C - Berlin, MD

Downtown Berlin

Christopher W.

CA $312 total

includes taxes & fees

Nov 9 - Nov 10

A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

9. Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

Michael V.

CA $417 total

includes taxes & fees

Nov 10 - Nov 11

A living room with a sofa, a coffee table, and a patterned rug. There is a window with curtains, a door, and a small table with chairs.

10. Historic Chesapeake City Stay

Chesapeake City

John P.

CA $400 total

includes taxes & fees

Nov 8 - Nov 9

A modern kitchen with white cabinets, a central island, and a dining area with a wooden table and chairs.

11. Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!

Midtown Ocean City

Ben P.

CA $281 total

includes taxes & fees

Nov 11 - Nov 12

A house with a paved walkway leading to the front door, surrounded by a landscaped garden with mulch and plants.

12. Country Get Away Studio Apartment

Elkton

JAMES V.

CA $130 total

includes taxes & fees

Nov 12 - Nov 13

A brick building with a white porch and a well-maintained lawn.

13. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

Mary Beth S.

CA $523 total

includes taxes & fees

Nov 11 - Nov 12

A waterfront property with multiple balconies, a dock with boats, and a clear blue sky.

14. Canal front with boat slip, boat ramp, WiFi, and roku streaming TV

Midtown Ocean City

Mindie F.

CA $214 total

includes taxes & fees

Nov 9 - Nov 10

A house with a blue front door, two windows, and a small porch.

15. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

lisa p.

CA $403 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

16. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

CA $338 total

includes taxes & fees

Nov 9 - Nov 10

A room with teal walls, a gray sofa, a white dresser, and a ceiling fan.

17. Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N

North Ocean City

Anonymous traveller

CA $274 total

includes taxes & fees

Nov 9 - Nov 10

A two-story house with a porch, two windows, and a door.

18. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Denton

Dallas S.

CA $492 total

includes taxes & fees

Dec 1 - Dec 2

A beachside table with a decorative centerpiece, two lanterns, and a view of the ocean.

19. BeachBox® III • Unreal Views • Oceanfront Balcony • Worcester House 401

Midtown Ocean City

Bethzaida

CA $316 total

includes taxes & fees

Nov 9 - Nov 10

A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

20. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

Anthony P.

CA $478 total

includes taxes & fees

Nov 23 - Nov 24

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Find vacation rentals that suit your style

Top Eastern Shore Hotel Reviews

A two-story house with a porch, a front door, and a small garden area.

The Wildset

Downtown St. Michaels

10/10 Excellent

Mairi

A beachfront property with a large tree, multiple buildings, and beach chairs.

Sandaway Suites & Beach

Oxford

10/10 Excellent

What a spectacular place. Rooms are somewhat colonial but so comfortable. The grounds are super and we got to drink wine and watch the sunset each night on Adaondak chairs. Each morning there was a basket at the door left quietly at 0700. Inside is a carafe of coffee, all the fixings, pastry, juice. Thete was also an area in the reception of help yourself to fruit, etc. I would give this higher than an excellent if I could. The town is cute and there is a ferry to the site as well. You'll love...

Elaine

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Anonymous traveller

A clear pool with palm trees, lounge chairs, and umbrellas.

Holiday Inn & Suites Ocean City by IHG

Downtown Ocean City

10/10 Excellent

Even though we visited during the off-season (October 22nd), one of the outdoor pools was still open and properly heated, and the entire property was well-maintained. The staff was top-notch! Our suite was spacious and clean, with all the amenities we needed for a great stay. Also worth mentioning: despite it being the off-season, the beaches were absolutely pristine! Just keep in mind that many of the surrounding attractions and restaurants on the island are closed during the off-season.

Carl

A hotel room with a bed, a desk, a chair, a TV, and a view of the ocean through a sliding door.

Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront

Downtown Ocean City

10/10 Excellent

The staff were friendly. The room was very clean. Housekeeping was very attentive and made sure to call and check up on us if we needed anything. My family and I really enjoyed the fact that the hotel was right on the boardwalk. Everything was close by. The food at the restaurant (Brother’s) in the lobby was also tasty. We didn’t use the hotel pool because my kids wanted to stay on the beach but it looked clean and well maintained. I recommend this hotel and I will definitely go back.

Natasha

Find out more about Eastern Shore

Everything you need to know about Eastern Shore vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Eastern Shore vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Eastern Shore vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Eastern Shore vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Eastern Shore. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Eastern Shore vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Eastern Shore vacation rentals we have selected for you start as low as CA $84 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Eastern Shore rentals

At Expedia, we put the best Eastern Shore vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Eastern Shore rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Eastern Shore vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Eastern Shore. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Eastern Shore Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Eastern Shore vacation rentals

1. Shore Point Cottages

2. Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

3. Salisbury Riverfront Lofts

4. Cambridge Apt in Walkable Neighborhood

5. Cass-N-Reel Luxury Houseboat

6. First Floor Studio Apartment in Historic Chestertown

7. Guest Suite for up to 2 in a Victorian on the Chester River

8. On Main Street - Apartment C - Berlin, MD

9. Charming Coastal/Country Home w/3 Acres & Sauna!

10. Historic Chesapeake City Stay

11. Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!

12. Country Get Away Studio Apartment

13. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

14. Canal front with boat slip, boat ramp, WiFi, and roku streaming TV

15. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

16. Sailwinds Loft at Cambridge Creek

17. Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N

18. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

19. BeachBox® III • Unreal Views • Oceanfront Balcony • Worcester House 401

20. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Find vacation rentals that suit your style

Top Eastern Shore Hotel Reviews

The Wildset

10/10 Excellent

Find out more about Eastern Shore

Eastern Shore vacation rentals: An excellent choice for every season

How to find incredible deals on Eastern Shore rentals

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