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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, (257)
"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, (22)
"We had a great time, the condo is lovely has great views, lots of space. The entire process from booking to checkout was a breeze! "
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)
"Excellent.communication with property manager. The house was beautiful with plenty of space for our group of 8."
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, (126)
"This was perfect for our group of friends and the hosts were very accommodating! "
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⭐️

9.6 out of 10, Exceptional, (29)
"Fantastic weekend at the beach watching football playoffs with the most beautiful woman in the world. Only issue was dead batteries in all the remotes. Quickly rectified by management "
⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️

Cottage near the Bay

8.8 out of 10, Excellent, (30)
"We enjoyed our stay. The host was very responsive to our needs and I appreciate her flexible schedule"
The price is AED 331
AED 724 total
includes taxes & fees
1 Apr - 2 Apr
Cottage near the Bay

Unit 1 South - End Unit Ocean Block Townhome

8.4 out of 10, Very Good, (45)
"We were in OC for the Country Calling concert, the location was great for us. Walking distance to Bad Monkey and Fagers Island was a plus! The host was very prompt in responding. "
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)
"This was our second time staying here. The place is a perfect spot- close to the beach, bars, restaurants and mini golf. Owners are very responsive. We look forward to retuning next year!!!"
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, (85)
"The owner lives next door and provides good introduction to our family. No issue. "
Welcome to Mabel Rose - Delightful 3 bedroom home on the Eastern Shore

Relaxing Breezy Seaside Retreat 3bd/2ba/2decks King Bed

10.0 out of 10, Exceptional, (21)
"This was a quick getaway for me and my kids but the house provided us with the R&R we needed. Location was wonderful being on the quiet end of the OC boardwalk. House was clean and had everything we needed. We enjoyed playing Ocean City Monopoly! Views of the beach were fantastic. We would love to stay here again."
Relaxing Breezy Seaside Retreat 3bd/2ba/2decks King Bed

Northside Park condo w/ Pool and Beach Supplies

10.0 out of 10, Exceptional, (5)
"We enjoyed our stay. Located right beside North Side Park with playground and much more. Kitchen was well stocked with things you need. If traveling with kids make sure to bring paper or plastic dishes for for them. I did bring my crock pot to make pulled pork while down at the beach. There is none in the kitchen. Plenty of hot water for showers.We would definitely stay here again."
Northside Park condo w/ Pool and Beach Supplies

Huge Boardwalk Direct Ocean Front Pool New Floor

9.8 out of 10, Exceptional, (90)
"A group of 10 came to OCMD to participate in the Ocean City Running Festival that occurred on Saturday,November 2nd. The condo was very accomodating to the group size. The living area was all open and we were able to relax and socialize comfortably. One drawback was only 2 bathrooms for a group this size but we made it work. The kitchen was well equiped, ice machine not working though. We were asked to wash linens prior to leaving if possible, but did not bring detergent with us since only...
Huge Boardwalk Direct Ocean Front Pool New Floor

Waterfront Ocean Pines Vacation Home w/ Boat Dock!

10.0 out of 10, Exceptional, (6)
"Rudy was a wonderful, caring, responsive and involved host. He contacted us frequently to make sure we were having a wonderful trip and made sure we had everything we needed for an enjoyable time. What a special person. The weather was above average the first 4 days so we got to enjoy the kayaks and we got to enjoy fishing off of the dock. The fireplace at night was beautiful. Great location to the area. Got to enjoy something different every day! Thank you so much… we will definitely be back ! "
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, (51)
"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)
"Location is perfect. The condo was very clean and Jennie was an awesome host. "
♡ 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)
"This met allour needs. Plenty of space for the whole family, awesome/new appliances. We enjoyed eating breakfast on the balcony watching the ocean. We've been coming to Ocean City for years and were staying in the condo high rises up in the 100 streets. We grew frustrated fighting for good beach space. You basically had to put you tent out at 7AM. Plenty of beach space in front of this place!"
EPIC RENOVATED PENTHOUSE Direct Oceanfront Huge Balcony View

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

9.8 out of 10, Exceptional, (34)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

The price is AED 496
AED 1,028 total
includes taxes & fees
3 Apr - 4 Apr
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

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (204)
"I love how quiet the place is. It gives you a remote feeling. A very nice getaway!"
Shore Point Cottages

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Great apartment "
Majestic Hotel & Apartments

Saint Tropez

3.0 star property
9.0 out of 10, Wonderful, (90)
"Relaxing and beautiful views with easy access to the beach. The room has all needed amenities: oven, coffee maker, microwave, washer and dryer. "
Saint Tropez
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.