Search Vacation Homes in Eastern Maryland

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Compare 570 Vacation Homes in Eastern Maryland with updated reviews, rates, and availability.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

10.0 out of 10, Exceptional, (26)
"Beautiful location and amazing views!"
PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Large 5 BR 4 BA Home is Ready for Family Fun!

10.0 out of 10, Exceptional, (6)
"Property was well maintained and very spacious. Would definitely return if in the area again."
Large 5 BR 4 BA Home is Ready for Family Fun!

Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!

9.8 out of 10, Exceptional, (79)
"Alway enjoy staying at this property. "
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!

DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

9.8 out of 10, Exceptional, (130)
"Great stay! Convention location, clean & spacious. Would definitely stay here again!"
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

5BR OceanView O/D Space/Movies, Pool, Bikes, Gear

9.6 out of 10, Exceptional, (27)
"The house was very nice, loaded with every thing needed for a pleasant stay. the kitchen had every appliance, silverware, gadget. The house was comfortable and decorated tastefully. The location was fabulous. The host was very attentive. It was an extremely pleasant stay. "
5BR OceanView O/D Space/Movies, Pool, Bikes, Gear

⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️

9.4 out of 10, Exceptional, (32)
"We enjoyed our stay in this condo with everything. Conveniently located, we loved the ocean views near the boardwalk. Restaurants and shops located nearby were a plus. The kitchen was well equipped and the bathrooms were spacious, not cramped. We would definitely stay here again!"
⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️

Cottage near the Bay

8.8 out of 10, Excellent, (29)
"Great time"
The price is SAR 338
SAR 740 total
includes taxes & fees
9 May - 10 May
Cottage near the Bay

Unit 1 South - End Unit Ocean Block Townhome

8.4 out of 10, Very Good, (45)
"Great location. Clean, steps to beach love this olace"
Unit 1 South - End Unit Ocean Block Townhome

Some Avail for 2025 Mid Town Ocean City on 69th St Townhome

9.6 out of 10, Exceptional, (56)
"The house was super cute- even more modern than the pics! Great location and cleanliness."
Some Avail for 2025 Mid Town Ocean City on 69th St Townhome

Welcome to Mabel Rose - Delightful 3 bedroom home on the Eastern Shore

10.0 out of 10, Exceptional, (88)
"Thoroughly enjoyed our stay here. EC was extremely helpful and a fantastic host."
Welcome to Mabel Rose - Delightful 3 bedroom home on the Eastern Shore

Relaxing Breezy Seaside Retreat Oceanfront, Boardwalk 3bd 2ba 2decks King Bed

10.0 out of 10, Exceptional, (24)
"This is an absolutely amazing place. Has everything you need. Very clean and excellent location. Highly recommend! "
Relaxing Breezy Seaside Retreat Oceanfront, Boardwalk 3bd 2ba 2decks King Bed

Northside Park condo w/ Pool and Beach Supplies

10.0 out of 10, Exceptional, (5)
"The place was beautiful. If we had any problems, the owner was a email away. We were close to restaurants and the beach. Definitely would rent this space again in the near future."
Northside Park condo w/ Pool and Beach Supplies

Huge Boardwalk Direct Ocean Front Pool New Floor

9.8 out of 10, Exceptional, (92)
"Our stay was absolutely amazing! The condo was huge plenty of room for all of our family. Kid friendly. Perfect placement on the boardwalk, close to everything! The hosts were wonderful and quick to respond with any questions. "
Huge Boardwalk Direct Ocean Front Pool New Floor

Waterfront Ocean Pines Vacation Home w/ Boat Dock!

10.0 out of 10, Exceptional, (9)
"Loved it!"
Waterfront Ocean Pines Vacation Home w/ Boat Dock!

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (53)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

♡ Brand New Modern & Luxury Beach Home Next to Boardwalk With Bay View

10.0 out of 10, Exceptional, (24)
"great location."
♡ Brand New Modern & Luxury Beach Home Next to Boardwalk With Bay View

EPIC RENOVATED PENTHOUSE Direct Oceanfront Huge Balcony View

9.4 out of 10, Exceptional, (13)
"Absolutely incredible spot. Location had an amazing view and beach access. Best place I’ve stayed at in a while!"
EPIC RENOVATED PENTHOUSE Direct Oceanfront Huge Balcony View

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (36)
"Very clean, great location"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

9.0 out of 10, Wonderful, (2)
"Nice and quiet place to stay"
The price is SAR 506
SAR 1,054 total
includes taxes & fees
14 May - 15 May
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
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.
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Other property types in Eastern Maryland

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Friendly staff and I was able to check in early. Would definitely stay here again next year!"
The price is SAR 243
SAR 333 total
includes taxes & fees
20 May - 21 May
Majestic Hotel & Apartments

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (212)
"The location is ideal for traveling to several towns in the area. We did find the sleeper sofa unusable (blocked the exit too much) and the kitchenette was lacking a few expected items. However, the unit was fantastic made for a great family vacation spot. We shall return."
Shore Point Cottages

Americana Condos 10th street

3.5 star property
8.4 out of 10, Very Good, (17)
"Just as seen in pictures very spacious and amazing location! Will definitely come back."
Americana Condos 10th street
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.