Eastern Shore Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Eastern Shore Vacation Homes

Our top choices for Eastern Shore vacation homes

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Property grounds

Adorable two-bedroom retreat close to Easton, Denton, Centreville

10.0 out of 10, Exceptional, (26)
"This home was perfect for a quiet getaway. Relaxing to come back to after a busy day out."
The price is CA $262
CA $495 total
includes taxes & fees
Aug 22 - Aug 23
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is CA $347
CA $581 total
includes taxes & fees
Aug 25 - Aug 26
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (49)
"Fit all of our needs. Clean,well furnished, nice kitchen. Stayed there twice and will probably go back."
The price is CA $319
CA $387 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront Getaway with Dock
Coastal Colonial Charm located in Ocean Pines
Beach

Coastal Colonial Charm located in Ocean Pines

8.8 out of 10, Excellent, (5)
"We stayed in Ocean pines. It made it convenient to go to ocean city, Berlin, and Assateague Island It was a nice place and perfect location"
The price is CA $229
CA $1,061 total
includes taxes & fees
Aug 22 - Aug 23
Coastal Colonial Charm located in Ocean Pines
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, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is CA $144
CA $423 total
includes taxes & fees
Aug 27 - Aug 28
Relax on Kent Island in 3 Bedroom Home w/Waterview
Cottage near the Bay
Dining

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is CA $112
CA $262 total
includes taxes & fees
Aug 24 - Aug 25
Cottage near the Bay
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Marina

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

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is CA $130
CA $405 total
includes taxes & fees
Aug 24 - Aug 25
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
6 Mi to Salisbury: Forest-View Sanctuary!
Outdoor dining

6 Mi to Salisbury: Forest-View Sanctuary!

9.0 out of 10, Wonderful, (2)
"Very nice secluded home but yet convenient to ocean city and salisbury. Found this home very peaceful and the property manager was very nice and helpful. Great place to have BBQ and crabs with family as we did. Will definitely return to this home."
The price is CA $114
CA $341 total
includes taxes & fees
Aug 26 - Aug 27
6 Mi to Salisbury: Forest-View Sanctuary!
Cozy Barn Loft: Country Views & Central to Beaches
1 bedroom, desk, travel crib, WiFi

Cozy Barn Loft: Country Views & Central to Beaches

10.0 out of 10, Exceptional, (18)
"Loft was spotless, and had everything we needed. "
The price is CA $186
CA $368 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Barn Loft: Country Views & Central to Beaches
Summer Rustic Camping with AC and King Bed
1 bedroom

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (4)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
The price is CA $129
CA $243 total
includes taxes & fees
Aug 25 - Aug 26
Summer Rustic Camping with AC and King Bed
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Property grounds

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

10.0 out of 10, Exceptional, (91)
"Enjoying Can’t wait to stay again"
The price is CA $208
CA $440 total
includes taxes & fees
Aug 24 - Aug 25
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Bayshore Beach Bungalow 46
Fridge, microwave, oven, stovetop

Bayshore Beach Bungalow 46

2.0 star property
Bayshore Beach Bungalow 46
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

8.6 out of 10, Excellent, (7)
"Nice and quiet place to stay"
The price is CA $193
CA $400 total
includes taxes & fees
Aug 25 - Aug 26
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Beachy Studio Condo with Pool and steps from the OC Boardwalk
Beach

Beachy Studio Condo with Pool and steps from the OC Boardwalk

9.0 out of 10, Wonderful, (7)
"Thanks for having us. Cost effective. Well maintained."
The price is CA $159
CA $443 total
includes taxes & fees
Aug 26 - Aug 27
Beachy Studio Condo with Pool and steps from the OC Boardwalk
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is CA $257
CA $556 total
includes taxes & fees
Aug 22 - Aug 23
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Beautiful Bayside Landing!
Outdoor dining

Beautiful Bayside Landing!

8.6 out of 10, Excellent, (7)
"Great property to stay at! 10 minutes from the beach, but also in a quiet, clean, and safe neighborhood. Easy check in progress, clean property, and would definitely stay again!"
The price is CA $101
CA $844 total
includes taxes & fees
Sep 16 - Sep 17
Beautiful Bayside Landing!
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (46)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is CA $277
CA $419 total
includes taxes & fees
Aug 24 - Aug 25
BAYSIDE BUNGALOW
Birdnest Beach Bungalow *Dog Friendly*
Exterior

Birdnest Beach Bungalow *Dog Friendly*

10.0 out of 10, Exceptional, (12)
"Nice visit "
The price is CA $237
CA $997 total
includes taxes & fees
Sep 6 - Sep 7
Birdnest Beach Bungalow *Dog Friendly*
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (43)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
The price is CA $327
CA $648 total
includes taxes & fees
Sep 3 - Sep 4
Beautiful Waterfront Retreat in Cambridge!
Salisbury Hideaway
Exterior detail

Salisbury Hideaway

10.0 out of 10, Exceptional, (19)
"We came to Salisbury to take a tour and this was the perfect place to stay. I was just about to book a hotel room when I found the Salisbury Hideaway. We appreciated how clean and fresh everything was. The kitchen and bathroom were well appointed and the beds were so comfortable. It was nice to have our own space. We woud definitely stay here again and recommend to friend's who have kids at SU. "
The price is CA $205
CA $491 total
includes taxes & fees
Sep 2 - Sep 3
Salisbury Hideaway
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Eastern Shore Hotel Reviews

Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

10/10 Excellent
"Have stayed here multiple times. Love the location. Great pool. Staff is always great. One drawback - the free WiFi in the oceanfront building is unreliable at best, but mostly nonexistent. Can’t speak for other areas of the property. "
Gail 4-night trip
Posted 10 hours ago
Days Inn by Wyndham Ocean City Oceanfront