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Compare 478 Vacation Homes in Eastern Shore with updated reviews, rates, and availability.

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

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

9.8 out of 10, Exceptional, (118)
"We were in Ocean City for our son's wedding. The condo fit our family and was in a great spot. We were able to walk up to the beach and take long walks on the beach. The condo was clean, large and had lots of parking. Convenient to the strip. Thank you!"
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15
PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck
Kitchen

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

10.0 out of 10, Exceptional, (15)
"This property is perfectly located on the boardwalk, had a perfect ocean view, a lot of space, and off street parking. We were all very pleased with this location and would 100% stay at this location again. Thank you for a great getaway!"
PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck
Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly

Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly

9.6 out of 10, Exceptional, (14)
"Loved the layout. Loved the property. Vacasa not so much. Was unsure what to bring. Put in a request they responded not only after we checked in but the day after we were there. They had the wrong days for trash collection. Shott of that tle beds ever!! Book!! It is a great neighborhood and place to stay property was amazong. Most comfortabcl"
Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly
Lovely beachfront condo with pool/hot tub access, scenic balcony & washer/dryer

Lovely beachfront condo with pool/hot tub access, scenic balcony & washer/dryer

8.0 out of 10, Very Good, (16)
"Incredible view of the beach with easy access. Convenient parking. Host was very responsive."
Lovely beachfront condo with pool/hot tub access, scenic balcony & washer/dryer
Waterfront allergy-free home with 40-foot fishing dock, canoe, home theater

Waterfront allergy-free home with 40-foot fishing dock, canoe, home theater

9.8 out of 10, Exceptional, (22)
"My 3 sisters flew in from around the country and we spent a long weekend in this house in the town of our childhood. Being together made for an amazing weekend but the house added to the enjoyment. It was clean, comfortable, well-stocked, and the neighborhood was quiet. We thoroughly enjoyed reconnecting in this beautiful home. I thought the lack of control of the heating/AC temp was going to be an issue, but a text to the local host and it was quickly resolved. Really appreciated her reaching...
Waterfront allergy-free home with 40-foot fishing dock, canoe, home theater
Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties
Living Area (1)

Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties

9.2 out of 10, Wonderful, (30)
"The unit was really nice and everything went well. "
Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties
Walk to Everything House
Front of House

Walk to Everything House

10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Nature,Outdoors,Scenery,Water,Waterfront

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (4)
"We had the most wonderful time at this charming house on Tillman Island! While the pics are great, it is even better in person. The house is perfectly nestled on the waterway, offering stunning views. The backyard pool was a true highlight, and we spent countless hours splashing around, the pool in the sun."
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Waterfront Townhouse! Gorgeous Sunsets! 2 Decks on Water!
Master bedroom deck at Sunset

Waterfront Townhouse! Gorgeous Sunsets! 2 Decks on Water!

9.8 out of 10, Exceptional, (166)
"Just wanted to say it was a perfect getaway the house was wonderful "
Waterfront Townhouse! Gorgeous Sunsets! 2 Decks on Water!
Beautiful Place, Amazing Location - Don't Miss out!!!
Living Room

Beautiful Place, Amazing Location - Don't Miss out!!!

9.4 out of 10, Exceptional, (45)
"This house was overall a great stay for 10 people. It was in a great location, checkin was super easy and the communication with the host was 10/10. About a week before check in we were sent check in instructions. The only thing I would say is that they did not provide towels or paper products and it’s really easy to forget things like bath mats and face cloths. Regardless, still a great stay. Also some of the blinds were broken when we arrived but it did not effect our sleeping."
The price is SAR 1,465
SAR 2,810 total
includes taxes & fees
29 Nov - 30 Nov
Beautiful Place, Amazing Location - Don't Miss out!!!
Pet-Friendly Home on Chester River w/ Dock!
Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
10.0 out of 10, Exceptional, (1)
Pet-Friendly Home on Chester River w/ Dock!
Dog-friendly home 5 blocks from the beach with patio, fireplace & prime location

Dog-friendly home 5 blocks from the beach with patio, fireplace & prime location

9.0 out of 10, Wonderful, (14)
"House was pleasant to stay in, and the dogs loved the fenced in backyard. The house smell like cat urine, and the washer has mold along the seal and in the detergent tray. "
Dog-friendly home 5 blocks from the beach with patio, fireplace & prime location
Beach Paradise 3-OCEANVIEW DOWNTOWN Luxury Townhome w/garage, steps to BOARDWALK
Living area

Beach Paradise 3-OCEANVIEW DOWNTOWN Luxury Townhome w/garage, steps to BOARDWALK

9.6 out of 10, Exceptional, (62)
"Great little place close to the beach. The townhouse is two story. There were plenty of beds and the kitchen was well stocked with appliances, plates and mugs. The view from the balcony gives you the ability to see the boardwalk and beach. The owners were very quick and easy to work with in regards to questions I had about the TV. Overall, great place for a family vacation!"
The price is SAR 188
SAR 1,159 total
includes taxes & fees
4 Dec - 5 Dec
Beach Paradise 3-OCEANVIEW DOWNTOWN Luxury Townhome w/garage, steps to BOARDWALK
The Blue House! Walk to the Beach! FirePit-Bikes-PingPong- Fully Fenced Yard!
Living area

The Blue House! Walk to the Beach! FirePit-Bikes-PingPong- Fully Fenced Yard!

10.0 out of 10, Exceptional, (43)
"We loved staying at the Blue House! It's in a super convenient, nice quiet neighborhood. Easy to get everywhere. Near a park and tiny free library. The house is so cute and comfy. They had everything we needed during our stay. My adult son enjoyed the N64. My hubby enjoyed the coffee making equipment! We had a great time and would definitely stay again. The host, Neil, is super attentive, friendly and helpful. Highly recommend! "
The Blue House! Walk to the Beach! FirePit-Bikes-PingPong- Fully Fenced Yard!
⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️
Building (1)

⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️

9.4 out of 10, Exceptional, (26)
"Great time in beautiful condo. Five stars all around. Outstanding location, comfort, amenities, convenience, service. Love it!"
⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
Exterior

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

9.8 out of 10, Exceptional, (119)
"This home is beautiful! Lots of light and space. We had such a great time we didn't want to leave. The location is perfect! The home is equipped with everything you need for an awesome vacation. We felt like Kim thought of everything. Just bring yourselves and enjoy "
The price is SAR 222
SAR 1,213 total
includes taxes & fees
9 Dec - 10 Dec
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
Interior

"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

9.8 out of 10, Exceptional, (107)
"Senior golfers enjoyed our stay at the condo. Close to dining and nightlife. Parking a plus with garage."
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront with private pier and great views

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (22)
"The pictures dont do this rental house justice. It was very clean and wonderfully decorated. The seperate unit was ideal for my daughter and her family. The "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
2-story end-unit townhome near beach with deck, AC, outdoor pool & fast WiFi

2-story end-unit townhome near beach with deck, AC, outdoor pool & fast WiFi

9.2 out of 10, Wonderful, (15)
"Perfect house for our 2 night stay. House had everything you could possibly need and was in a nice quiet neighborhood, perfect for family getaway. We really enjoyed the front porch in the evening. Place was nice and clean and exactly how it is pictured."
2-story end-unit townhome near beach with deck, AC, outdoor pool & fast WiFi
Beautifully Remodeled 3 BR, Ocean Pines, 6 miles to Ocean City
Property grounds

Beautifully Remodeled 3 BR, Ocean Pines, 6 miles to Ocean City

9.4 out of 10, Exceptional, (24)
"short stay but enjoyable"
Beautifully Remodeled 3 BR, Ocean Pines, 6 miles to Ocean City
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

Shore Point Cottages
Exterior

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (199)
"These cottages were so cute and the area was nice we had everything we needed and it was very convenient getting to the ocean's calling festival we were going to. I would definitely recommend these cottages if you are headed out to Ocean City."
The price is SAR 409
SAR 577 total
includes taxes & fees
5 Dec - 6 Dec
Shore Point Cottages
Majestic Hotel & Apartments
Exterior

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Great apartment "
Majestic Hotel & Apartments
Beachfront condo with private balcony & amazing views

Beachfront condo with private balcony & amazing views

9.2 out of 10, Wonderful, (20)
"We prefer N. Ocean city. Property has a nice living room and kitchen. Huge TV on the wall if you need it. The bedroom is set up with double queens and 1/2 a bath. The mattresses were not comfortable for me. I would have preferred the TV to be up higher in the bedroom as it was hard to see lying down. We had a good time and would stay again.I appreciated the linens being supplied!"
Beachfront condo with private balcony & amazing views
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.