Search Vacation Homes in Eastern Shore

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Compare 595 Vacation Homes in Eastern Shore with updated reviews, rates, and availability.

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (184)
"My husband, children and grandchildren spent a wonderful 5 days at Love Point Idyll. The house is large and beautiful with great views of the bay and wildlife. We took many walks around the property when the weather permitted and when we weren’t visiting nearby DC. The house was well stocked with necessities and Hal was extremely gracious and quick to answer any questions. We had so much fun and the family is eager to go back for another visit. "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"The house was perfect. While the weather didn't really cooperate still had time to sit on the dock and the porch watching the eagles, osprey, geese, ducks, birds and fishermen. Location near Charlestiwn and NorthEast us freat fir restaurants and shopping "
Captivating Chesapeake experience

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

10.0 out of 10, Exceptional, (23)
"Our condo had it all; space, kitchen equipment, unbelievable views, and most of all a comfortable bed. The owner thought of everything to make our 4 day stay perfect."
PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

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!

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (27)
"Nice and peaceful stay for a quick local getaway. "
The price is SAR 232
SAR 898 total
includes taxes & fees
28 Apr - 29 Apr
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

9.8 out of 10, Exceptional, (128)
"Plenty of bedrooms for accomodations. Great location on the island. Host provided everything needed for a comfortable stay."
The price is SAR 732
SAR 1,832 total
includes taxes & fees
21 May - 22 May
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)
"Very nice property…one of the best. The host was very responsive and kind ! We are coming back this summer and hoping we can get this property again ! "
⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️

Cottage near the Bay

8.8 out of 10, Excellent, (29)
"We have stayed here before and will again."
The price is SAR 338
SAR 740 total
includes taxes & fees
3 May - 4 May
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

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

10.0 out of 10, Exceptional, (87)
"The owner was so kind and walked us through everything, even setting all of us up on the wifi and streaming apps. The house was really clean, and had a perfect location for our visit. Will definitely be back next year"
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, (23)
"Located almost right in the middle of the boardwalk. Perfect location. Perfect view and well kept house. Exactly as pictured. It was a very relaxing week and hope to get back there someday!"
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)
"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, (8)
"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

8.0 out of 10, Very Good, (1)
"Nice and quiet place to stay"
The price is SAR 506
SAR 1,066 total
includes taxes & fees
28 Apr - 29 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 Shore

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Great apartment "
The price is SAR 219
SAR 306 total
includes taxes & fees
19 May - 20 May
Majestic Hotel & Apartments

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (207)
"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

Saint Tropez

3.0 star property
9.2 out of 10, Wonderful, (98)
"We love waking up to the ocean views in a quiet area"
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.