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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct
Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!
Fridge, microwave, oven, stovetop

Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!

9.6 out of 10, Exceptional, (109)
"Had a great time house was very clean!"
Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!
⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️
Property grounds

⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️

9.2 out of 10, Wonderful, (7)
"The location was amazing! Just steps from the beach! The condo was a perfect size for our family which was 5 adults and 2 young kids. It had everything we needed."
The price is HK$2,296
HK$5,173 total
includes taxes & fees
1 Sept - 2 Sept
⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️
Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (166)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach
Wave Watcher's Condo - Steps to the beach!
Interior

Wave Watcher's Condo - Steps to the beach!

9.8 out of 10, Exceptional, (7)
"The place was very clean and very cool, which was nice on the hot days. Some of my party slept on the floor so I'd say it sleeps 10 but overall, wonderful place would recommend to anyone!"
Wave Watcher's Condo - Steps to the beach!
Coastal Cottage - 2BR Home with 2 Pools, pond, & 1000ft pier in Assateague Point
Exterior detail

Coastal Cottage - 2BR Home with 2 Pools, pond, & 1000ft pier in Assateague Point

2.0 star property
10.0 out of 10, Exceptional, (17)
"Great place to stay great friendly people in neighorhood. Very clean and everything u need is right there in the house. Would definitely go back."
Coastal Cottage - 2BR Home with 2 Pools, pond, & 1000ft pier in Assateague Point
Sunset Island is Loved for it's Amazing Amenities
Exterior

Sunset Island is Loved for it's Amazing Amenities

Sunset Island is Loved for it's Amazing Amenities
Bayfront cottage offers amazing views of the water and Assateague Island
Terrace/patio

Bayfront cottage offers amazing views of the water and Assateague Island

9.6 out of 10, Exceptional, (40)
"Wonderful stay! Very clean and relaxing!"
Bayfront cottage offers amazing views of the water and Assateague Island
Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes
Fridge, microwave, oven, stovetop

Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes

8.8 out of 10, Excellent, (3)
"property was very clean, lot of space everything was equipped in kitchen for cooking. plus kids toys. We had a great time staying that the property."
Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes
Stay & Play at Our Beautiful Retreat
Pool

Stay & Play at Our Beautiful Retreat

10.0 out of 10, Exceptional, (3)
"This property has everything you need for a friends weekend. Pickelball, pool, basketball, even golf hitting net were all used by our group and we enjoyed the TV room and large outdoor space. Takes a little navigating to get there, but the directions were well done and communication with the owner was great. They were very responsive to all of our questions. Would highly recommend this place for groups."
Stay & Play at Our Beautiful Retreat
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Marina

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
⭐️Gorgeous Sunset Island Private Beach In/Outdoor Pools⭐️
Indoor pool, outdoor pool

⭐️Gorgeous Sunset Island Private Beach In/Outdoor Pools⭐️

9.4 out of 10, Exceptional, (13)
"My family loves Sunset Island. We thoroughly enjoyed staying at this condo. "
⭐️Gorgeous Sunset Island Private Beach In/Outdoor Pools⭐️
Pet-Friendly Home on Chester River w/ Dock!
Interior

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (13)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!
Historic home on Smith Island w/ dock!
Beach

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (43)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!
5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+
Outdoor dining

5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+

The price is HK$13,306
HK$21,104 total
includes taxes & fees
24 Aug - 25 Aug
5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+
Water front, open bay views from both decks!!
Interior

Water front, open bay views from both decks!!

10.0 out of 10, Exceptional, (70)
"Great place to stay!"
Water front, open bay views from both decks!!
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is HK$981
HK$2,546 total
includes taxes & fees
2 Sept - 3 Sept
Relax on Kent Island in 3 Bedroom Home w/Waterview
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!
Exterior detail

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

9.8 out of 10, Exceptional, (84)
"Alway enjoy staying at this property. "
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!
Charming dog-friendly townhouse with pool - near beach
Property grounds

Charming dog-friendly townhouse with pool - near beach

8.0 out of 10, Very good, (111)
"Fine stay nice house. Easy to use codes. Beds comfortable. "
Charming dog-friendly townhouse with pool - near beach
Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
Fridge, microwave, oven, stovetop

Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool

9.8 out of 10, Exceptional, (44)
"This is a nice property located a short drive or "
Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
Lord Guy Retreat in Ocean Pines 3bd
Microwave, dishwasher, coffee/tea maker

Lord Guy Retreat in Ocean Pines 3bd

2.0 star property
Lord Guy Retreat in Ocean Pines 3bd
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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Top Eastern Shore Hotel Reviews

Ashore Resort & Beach Club

Ashore Resort & Beach Club

10/10 Excellent
"Everything was excellent and the service could not have been better. Very attentive to our needs. Perfect size hotel that you are not just another guest."
Anonymous traveller 3-night trip
Posted 6 hours ago
Ashore Resort & Beach Club