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Vacation rentals in Eastern Shore

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Top-rated vacation rentals in Eastern Shore

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Tiny home in Cambridge

4.89 out of 5 average rating, 497 reviews

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette 5 min away from Blackwater Refuge! It is an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! Staying the cabin will make your visit even more memorable!The Tiny Cabin is now located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

Aug 31 – Sep 7

G$18,194 GYD per night

Apartment in Dewey Beach

4.95 out of 5 average rating, 133 reviews

DeweyBeach 1 BR + sleeper sofa. Walk to the beach!

Enjoy all of Dewey Beach at this delightful 1 BR, ground floor, apartment on the north side of town. 1.5 blocks to the beach, and 3 blocks to the start of restaurants and music venues. Quiet, relaxing location on a side street. Perfect for a small family or group of 4 friends! Custom self check-in keypad code for Private Entry sent upon booking. Professionally cleaned + bed made before your stay. 4 beach chairs, 1 on-property parking spot + 1 free Street Parking Passes provided at no charge!

Dec 23 – 30

G$18,581 GYD per night

Tiny home in Snow Hill

4.89 out of 5 average rating, 225 reviews

Private cottage and gardens/comfortable queen bed.

Private cottage and gardens, comfortable Queen bed, full bath and kitchenette, within walking distance to historic Snow Hill. 30 min. drive to Ocean city and Assateague Island National park. This cottage was once a old school woodworking shop which is now on display at the old iron furnace town museum nearby. This beautiful three hundred year old town sits on the beautiful Pocomoke river with canoe, kayak, and bike rentals. Museums, art galleries, speciality shops, food and entertainment.

Aug 10 – 17

G$25,859 GYD per night

Apartment in Greenwood

4.97 out of 5 average rating, 477 reviews

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Sep 19 – 26

G$17,169 GYD per night

Tiny home in Selbyville

4.98 out of 5 average rating, 211 reviews

Destination Location! Farm Animals, Tours, Beaches

Scratch staying in a tiny house off your bucket list! Escape the Ocean City crowds and slow life down at this Garden Hideaway. Situated on a ranch just minutes from the beach, this unique home has a barnyard of fuzzy animals ready to greet you each day. Curated to both inspire joy and create presence, enjoy a simple morning and sip coffee with Fonzie the alpaca, Charlotte the mini-pig and a front yard of silly goats sure to entertain. This is a magical stay that we're certain you'll love!

Sep 18 – 25

G$27,928 GYD per night

Home in Ocean View

4.92 out of 5 average rating, 531 reviews

Tiny House at Good Earth, near Bethany Beach

A custom-built "Tiny House" located right between our new dinner theater and our garden dining area. True to the show "Tiny House Nation"; cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TVs and internet in the units but the quality of service is not guaranteed. We are in a rural area and sometimes it's slow or not working at all. If TV and internet are super important for your stay we may not be the right fit.

Apr 28 – May 5

G$25,437 GYD per night

Guesthouse in Easton

4.99 out of 5 average rating, 543 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.

Nov 10 – 15

G$30,014 GYD per night

Condo in Ocean City

4.97 out of 5 average rating, 223 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Nov 8 – 15

G$23,059 GYD per night

Guest suite in Berlin

4.99 out of 5 average rating, 148 reviews

Berlin/Ocean City Suite- Relax/Refresh near beach!

A remodeled, above garage guest suite separate from the main house in America's Coolest Small Town, Berlin Md! You will benefit from a separate entrance to your above garage suite which will allow you to enjoy your own quiet space to relax and embrace the small, quaint town of Berlin, all while a mere 15 minutes to the beaches of OCEAN CITY and Assateague! Multiple dining experiences and tons of shopping await you in either historic Berlin or world famous Ocean City!

Jan 30 – Feb 6

G$23,818 GYD per night

Apartment in Frankford

4.98 out of 5 average rating, 122 reviews

Cozy Cottage Getaway

Enjoy this newly remolded 1 bedroom apartment tucked away on 2+ acres 3 miles from Bethany beach. Close to Rehobeth beach for outlet tax free shopping or Ocean City MD just 13 miles. You’ll be minutes away from lots of restaurants, stores, mini golf, arcade, night life etc. Property includes a 1/4 mile walking/running trail, fire pit and basket ball court. This is the perfect place to escape away from the busy Beach life but close enough to enjoy everything fully.

Oct 8 – 15

G$25,943 GYD per night

Apartment in Milton

4.96 out of 5 average rating, 132 reviews

Beachin' Inn Milton

Welcome to Beachin' Inn Milton! This cozy apartment located in the quaint, historical town of Milton, DE is the perfect getaway. Our apartment is light and airy with a beach theme. Enjoy the entire apartment to yourself with a keyless private entrance, full bath, washer/dryer, free Wifi and stocked assorted coffee pods. There is no stove/oven, however, we offer a microwave, toaster oven, Air Fryer and induction burner.There is private parking right out front.

May 2 – 9

G$24,891 GYD per night

Guest suite in Chincoteague

4.93 out of 5 average rating, 223 reviews

Baywatch North-Waterfront & Roaming Ponies

This is a lovely space! 2 queen bedroom unit decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, patio cooking area shared with upstairs unit, bbq grill, fantastic view, beach items, plenty of parking, private lane, very quiet out of the way of everything, super laid back host living in the other portion of the house. Labrador and cat on premises, ponies on premises!

Oct 21 – 28

G$25,249 GYD per night

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Popular amenities for Eastern Shore vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Eastern Shore

Apartment in Frederica

4.97 out of 5 average rating, 258 reviews

Smokefree Lakeside Relaxation

Dec 25 – Jan 1

G$15,785 GYD per night

Guest suite in Berlin

4.97 out of 5 average rating, 529 reviews

Ayers Creek Carriage House

Jul 9 – 16

G$37,640 GYD per night

Farm stay in Madison

4.98 out of 5 average rating, 161 reviews

Madison Nature Getaway

Aug 5 – 12

G$25,825 GYD per night

Condo in Ocean Pines

4.96 out of 5 average rating, 106 reviews

Quiet Water View Condo

Nov 9 – 16

G$28,958 GYD per night

Guest suite in Cape May

4.97 out of 5 average rating, 286 reviews

Dragonfly Cottage

Nov 14 – 21

G$22,653 GYD per night

Apartment in Salisbury

4.88 out of 5 average rating, 50 reviews

Contemporary & Cozy Guesthouse

Jan 11 – 18

G$20,905 GYD per night

Home in Parsonsburg

4.95 out of 5 average rating, 22 reviews

Charming Home in a Neighborhood

Sep 15 – 22

G$32,508 GYD per night

Apartment in Salisbury

4.92 out of 5 average rating, 37 reviews

Salisbury Maryland (Central)

May 25 – Jun 1

G$23,930 GYD per night

Destinations to explore