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Vacation rentals in Eastern Shore

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Top-rated vacation rentals in Eastern Shore

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Tiny home in Cambridge

4.89 out of 5 average rating, 496 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!

Nov 19 – 26

R1,608 ZAR per night

Farm stay in Madison

4.98 out of 5 average rating, 162 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Feb 16 – 23

R2,362 ZAR per night

Tiny home in Snow Hill

4.89 out of 5 average rating, 226 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 13 – 20

R2,365 ZAR per night

Apartment in Greenwood

4.97 out of 5 average rating, 479 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)

Nov 17 – 24

R1,570 ZAR 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!

Nov 21 – 28

R2,993 ZAR 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.

Dec 18 – 25

R2,326 ZAR per night

Apartment in Frederica

4.97 out of 5 average rating, 258 reviews

Smokefree Lakeside Relaxation

Quiet smoke free lakefront Carriage House studio over garage with separate entrance. Mini Fridge, microwave, dishes. Use of fire pits, canoe, SUP, dock. Lake is fishable and swimmable. Flatscreen HDTV with Premium Channels. WiFi to use with your own device or use my laptop in unit. 45 min from beach. 20 minutes to Dover. 4 parks with walking paths within 10 miles. Close to Dover Air Force Base but not in flight path. Well behaved social pets with responsible owners are welcome!

Sep 9 – 16

R1,239 ZAR per night

Guesthouse in Easton

4.99 out of 5 average rating, 545 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 19 – 24

R2,745 ZAR per night

Guest suite in Cape May

4.97 out of 5 average rating, 287 reviews

Dragonfly Cottage

Dragonfly Cottage is a hotel style unit with queen bed on a quiet street on Cape May Island a mile from the beach and town. It is a bright, sunny room with a vaulted ceiling, private entrance, off street parking and screened in porch for having your morning coffee. Located in easy biking distance to both Cape May, West Cape May and the Point, it is a good base for a great vacation. Beach tags and beach chairs provided. Come have a comfortable getaway at the shore!

Nov 14 – 21

R2,072 ZAR per night

Guest suite in Berlin

4.99 out of 5 average rating, 149 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!

Mar 4 – 11

R2,178 ZAR per night

Apartment in Frankford

4.98 out of 5 average rating, 123 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 13 – 20

R2,855 ZAR 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.

Oct 8 – 15

R2,276 ZAR per night

Vacation rentals for every style

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Popular amenities for Eastern Shore vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Eastern Shore

Condo in Ocean Pines

4.96 out of 5 average rating, 107 reviews

Waterview Retreat

Jan 10 – 17

R2,648 ZAR per night

Bungalow in Fruitland

4.93 out of 5 average rating, 112 reviews

Nana's Cottage, a place of comfort and peace

Sep 28 – Oct 5

R2,143 ZAR per night

Apartment in Berlin

4.94 out of 5 average rating, 152 reviews

Lovely 2 bedroom overlooking Main St.

Mar 30 – Apr 6

R2,798 ZAR per night

Condo in Ocean City

4.99 out of 5 average rating, 175 reviews

Direct Oceanfront close to Northside Park!

Dec 21 – 28

R2,313 ZAR per night

Guest suite in Berlin

4.97 out of 5 average rating, 529 reviews

Ayers Creek Carriage House

Jul 9 – 16

R3,586 ZAR per night

Guest suite in Rehoboth Beach

4.98 out of 5 average rating, 122 reviews

Treetops beach getaway walkable to beach/boardwalk

Mar 17 – 24

R2,318 ZAR per night

Apartment in Salisbury

4.88 out of 5 average rating, 51 reviews

Contemporary & Cozy Guesthouse

Feb 4 – 11

R2,823 ZAR per night

Camper/RV in Salisbury

5.0 out of 5 average rating, 15 reviews

There is no place like GNOME! Camping on a farm!

Mar 27 – Apr 3

R1,641 ZAR per night

Destinations to explore