Holiday Homes in Eastern Shore

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Featured Holiday Homes in Eastern Shore

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

10.0 out of 10, Exceptional, (17)
"This was great and place to stay, great location, very quiet, secure, easy access and absolutely beautiful view. Loved it "
PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

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, (123)
"Me and my three friends really enjoyed our stay at this spacious and beautiful townhouse. Check in/out was easy. It was very much the off season and we enjoyed the beautiful and peaceful neighborhood. "
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

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.

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 "
The price is AU$560
includes taxes & fees
17 Jan - 18 Jan
Beach Paradise 3-OCEANVIEW DOWNTOWN Luxury Townhome w/garage, steps to BOARDWALK

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

9.8 out of 10, Exceptional, (79)
"Alway enjoy staying at this property. "
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!

Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties

9.2 out of 10, Wonderful, (34)
"The condo community and city have a variety of entertainment amenities, especially helpful for winter guests who may not want as much beach time. We especially enjoyed walking the boardwalk at the center of town. The condo offers great bay and ocean views from large windows and has ample deck spaces. Furnishings are older yet adequate for our family of mostly adults and teens."
Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties

On The Water * Private Dock * Sunset Porch Views

9.8 out of 10, Exceptional, (38)
"Loved staying here! Pay attention to the description by the owner! The house takes you back in time a little bit, but it’s so nice! Great location, nice neighborhood. The main living area is larger in person than what it looks like in the photos. We have already booked our next stay here!"
On The Water * Private Dock * Sunset Porch Views

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. "
The price is AU$504
includes taxes & fees
11 Feb - 12 Feb
BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

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.

Walk to Everything House

10.0 out of 10, Exceptional, (75)
"House was centrally located in town. We parked the car and walked! Beds were very comfortable it was wonderful to have seperate beds for everyone. Well stocked kitchen. Washer & dryer a plus. We will be back. "
Walk to Everything House

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (47)
"Nice place "
Dollhouse in Central Historic St Michaels

Island style beach cottage

10.0 out of 10, Exceptional, (15)
"Our second stay was as awesome as the first. Great location, awesome host ...we can't wait for next year 😁"
Island style beach cottage

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

9.6 out of 10, Exceptional, (19)
"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️

9.6 out of 10, Exceptional, (27)
"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)
"this is third year for our family Christmas. very nice place with plenty of room. always clean and decorated for the holidays"
The price is AU$506
includes taxes & fees
15 Jan - 16 Jan
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

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.

Boardwalk Bungalow | Whole House Downtown OC

9.2 out of 10, Wonderful, (26)
"Great location close to boardwalk and beach. The property was old but everything was clean and in working condition. I would have given 5 stars but some beds were uncomfortable. "
Boardwalk Bungalow | Whole House Downtown OC

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
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 "
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.