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Top Holiday Rentals in Somerset County

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!

Cottage near the Bay

9.0 out of 10, Wonderful, (41)
"great, peaceful "
The price is £144
includes taxes & fees
10 Aug - 11 Aug
Cottage near the Bay

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (163)
"excellent place to stay on the water"
Blufin Bungalows & Marina

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (420)
"Beautiful pool areas, lots to do, and plenty of room with a family of 5! "
Key West Cottages

Strawberry Crossroads

2.0 star property
8.4 out of 10, Very good, (5)
"My family really enjoyed the stay, its close enough drive to ocean city while being out of the way. Even after having a double booking issue the property owner made it work for us all. The kids were begging us to stay longer it was so peaceful!"
Strawberry Crossroads

2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

9.6 out of 10, Exceptional, (46)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

9.6 out of 10, Exceptional, (42)
"We enjoyed our stay at Waterside. Location was perfect and host was very responsive to questions. A great rental for a few friends and/or family."
The price is £351
includes taxes & fees
2 Sept - 3 Sept
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

10.0 out of 10, Exceptional, (54)
"An instant nervous system reset."
The price is £233
includes taxes & fees
4 Sept - 5 Sept
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

'river's Edge Retreat With Kayaks & River Access!

3.0 star property
'river's Edge Retreat With Kayaks & River Access!

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (32)
"Small Cozy condo for couples. Very quiet and relaxing with great sunrises and sunsets! Great location with being on the water!"
Waterfront on Marsh Island!

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (171)
"Beautiful cabin situated at the back of a farm, very peaceful. Very spacious and inviting. Only a half hour to Chincoteague and an hour to Ocean City. Nice porch with a swing and 2 chairs to sit out in the morning with a cup of coffee (coffee maker provided). We loved having a pool table for our evening entertainment. Only thing we didn't like was the very tiny kitchen, absolutely no counter space at all :( "
Cabin at Holdens Creek on Eastern Shore of VA

5 minutes to Assateague National Seashore!

8.8 out of 10, Excellent, (16)
"There was enough space for 3 adults and to children. The bathroom in the hall has not been updated. The shower was crudy and no towel rack. The spicket for shower/bath in the 2nd bathroom was almost impossible to use. The rental was okay."
The price is £167
includes taxes & fees
18 Aug - 19 Aug
5 minutes to Assateague National Seashore!

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (117)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

NEW PET FRIENDLY LISTING ALERT!!

9.4 out of 10, Exceptional, (12)
"Lovely home right on the river- fishing to your hearts content Clean, lots to do very peaceful!!! Would definitely come back! Mia is great to work with"
NEW PET FRIENDLY LISTING ALERT!!

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (17)
"Nice place. "
The price is £176
includes taxes & fees
9 Sept - 10 Sept
Only 5 min to Assateague National Seashore!

Spacious waterfront home with dock and sunset view

9.4 out of 10, Exceptional, (6)
Spacious waterfront home with dock and sunset view

The purple door at the bay.

9.2 out of 10, Wonderful, (51)
"Property was slightly run down and had no driveway (just grass). It was in a great neighborhood with a beautiful view. We had to take the trash 15 minutes south when leaving (in the opposite direction of home for us). It was good enough for us to relax and cook but a slight bit expensive for its outdated condition though."
The price is £358
includes taxes & fees
24 Aug - 25 Aug
The purple door at the bay.

Salisbury Riverfront Lofts

3.0 star property
9.2 out of 10, Wonderful, (21)
"Very nice place clean & roomy."
The price is £191
includes taxes & fees
13 Aug - 14 Aug
Salisbury Riverfront Lofts

Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.

10.0 out of 10, Exceptional, (142)
"Perfect cozy place to stay at the end of a quiet pine tree lined street with easy access to the national park and all it offers."
Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.

Small cottage for those little getaways

10.0 out of 10, Exceptional, (112)
"Great place, cozy and easy to park and get around. "
Small cottage for those little getaways
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 Somerset County Hotel Reviews