Search Vacation Homes in Eastern Shore

Compare 484 Vacation Homes in Eastern Shore with updated reviews, rates, and availability.

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.0 out of 10, Wonderful, (2)
"no kettle no cutting board"
Pet-Friendly Home on Chester River w/ Dock!

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

9.6 out of 10, Exceptional, (122)
"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

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

9.8 out of 10, Exceptional, (78)
"We loved our stay and hope to return. All 5 bedrooms are very roomy with their own private full bath. Plenty of space for relaxing and eating. The kitchen has everything you will need."
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

10.0 out of 10, Exceptional, (16)
"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

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

9.6 out of 10, Exceptional, (67)
"Clean, close to shops and dining "
Beach Paradise 3-OCEANVIEW DOWNTOWN Luxury Townhome w/garage, steps to BOARDWALK

Waterfront Getaway-walk to beach and local favorites!

10.0 out of 10, Exceptional, (29)
"We had a great stay at Bonita on the Bay! Paula was very communicative and helpful and the home was clean, comfortably, and well equipped. I have stayed in Ocean City many times, but never in this particular neighborhood; we were there one week after Labor Day and found the area to be quiet and pleasant with plenty of friendly people around. Being on a canal (as the pictures accurately show), I had slight concerns that the water view would feel closed in with the other houses around. There...
Waterfront Getaway-walk to beach and local favorites!

3 Bedroom/2 Bathroom Downtown Ocean City Home w/ a Pool

9.4 out of 10, Exceptional, (26)
"My group enjoyed our stay at this property. Excellent location near boardwalk. Next to convenient deli. Host messaged us in advance to let us know that the home comes with a small starter supply of toilet paper/paper towels, so renters should consider bringing additional supply for convenience depending on size of group/length of stay."
3 Bedroom/2 Bathroom Downtown Ocean City Home w/ a Pool

BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

9.8 out of 10, Exceptional, (38)
"Very nice and clean condo. We had a great stay. "
BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

Saint Louis Ave townhouse central AC & private washer/dryer - near the ocean

7.8 out of 10, Good, (19)
"Took my boys with friends for a long weekend and enjoyed our stay. Place was close enough to walk to beach and we enjoyed our stay. Place was easy to communicate with them during the stay."
Saint Louis Ave townhouse central AC & private washer/dryer - near the ocean

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

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

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (46)
"This was a comfortable home, and a nice location. We were staying mostly for business, so didn’t do much in town, but the main restaurant and shopping areas are two short blocks away. We did use the nearby nature trail to walk our dogs. The only concerns others might have with the house, and the reason for four stars instead of five, were: minimal kitchen equipment (few pots/pans etc.), steep narrow stairs to the second floor, and low water pressure in the shower. That said, none of these things...
Dollhouse in Central Historic St Michaels

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

10.0 out of 10, Exceptional, (21)
"Lovely, quiet and comfortable home not far from route 50, nearby shopping, close to a wonderful Italian restaurant in Stevensville, and 20 minute drive to Annapolis. Owner was very responsive with a few questions we had during our stay. We would definitely stay again. "
The price is SAR 256
SAR 905 total
includes taxes & fees
5 Jan - 6 Jan
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Four Bedroom Oceanside Townhome with Pool and View

8.0 out of 10, Very Good, (1)
"Overall, it was a nice stay. The property was found as advertised; however, there was an infestation of ants that we battled all week. There were ant traps in the property when we arrived and we purchased more throughout the week. The bedding was stained in some places as well. The accuracy of information about access to the pool was a bit frustrating at first. But we got that sorted out rather quickly. The location to the ocean was amazing and very convenient with young children!"
Four Bedroom Oceanside Townhome with Pool and View

⭐️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!

9.8 out of 10, Exceptional, (121)
"Our booking was very nice, perfectly placed close to the beach and other things to do, and very clean. "
The price is SAR 184
SAR 1,163 total
includes taxes & fees
3 Feb - 4 Feb
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

Large estate & cottage with private pool, firepits, & game room

7.8 out of 10, Good, (53)
"The house is simply not what it advertised. We followed the previous vacationers, and the dishwasher still did not work. We had an issue adjusting the water temperature in both the king suite and the upstairs shower. The king suite could not be adjusted (adjuster frozen), and they never sent anyone. We could not use the room off the pool because there was an issue with odor and the air conditioner. We loved spending time by the pool fireplace area however it should have been power washed for the...
Large estate & cottage with private pool, firepits, & game room

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

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (33)
"Perfect for our weekend stay. Checkin was easy and communication with the owner was great! Definitely would stay again. Kentmoor restaurant was awesome. Filled with locals who were friendly and welcoming! Food was great!"
The price is SAR 296
SAR 962 total
includes taxes & fees
15 Jan - 16 Jan
Relax on Kent Island in 3 Bedroom Home w/Waterview

Boardwalk Bungalow | Whole House Downtown OC

9.2 out of 10, Wonderful, (25)
"This is a classic beach cottage right in downtown OC - perfect for what we needed for our long weekend. We were able to walk to everywhere we needed to go. We will book again!"
Boardwalk Bungalow | Whole House Downtown OC
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.
Don't see what you're looking for?
See all available properties in Eastern Shore
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Eastern Shore

Majestic Hotel & Apartments

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

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (201)
"Awesome place to visit "
Shore Point Cottages

Coconut Malorie Resort Ocean City a Ramada by Wyndham

3.0 star property
7.4 out of 10, Good, (1236)
"Nice to have a kitchen and separate bedroom "
Coconut Malorie Resort Ocean City a Ramada by Wyndham
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.