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Eastern Shore vacation rentals

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Top-rated vacation rentals in Eastern Shore

Guests agree: these vacation rentals 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!

Sep 23 – 30

G$17,547 GYD per night

Loft in Cape May Court House

4.97 out of 5 average rating, 590 reviews

Quiet Lakefront Studio - Close to the Beach

Discover Cape May County - the hidden gem of Southern New Jersey. Be our guest on a crystal clear lake surrounded by tall pines and wetlands, creating a vast wildlife habitat in a sanctuary of natural artistry. Great care has been taken to nurture a secluded environment to explore, restore and create; all on a hidden lake with its own sandy beach. Local beach passes, hiking trails, direct access to the county bike path, fire pit, hammocks, water sports, etc. are all included in your stay.

Nov 28 – Dec 5

G$27,821 GYD 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 10 – 17

G$25,809 GYD 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 24 – Dec 1

G$17,136 GYD per night

Loft in Lusby

5.0 out of 5 average rating, 312 reviews

Coastal Treetop Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction stove, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

Jan 19 – 26

G$26,522 GYD 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!

Oct 27 – Nov 3

G$15,021 GYD 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.

Mar 22 – 27

G$29,956 GYD 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

G$22,610 GYD 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!

Oct 11 – 18

G$23,772 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.

Sep 13 – 20

G$24,843 GYD per night

Apartment in Lexington Park

5.0 out of 5 average rating, 316 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Nov 21 – 28

G$18,333 GYD per night

Guest suite in Chincoteague

4.93 out of 5 average rating, 224 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$21,452 GYD per night

Vacation rentals for every style

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Popular amenities for Eastern Shore vacation rentals

Laptop-friendly workspace

Air conditioning

Other great vacation rentals in Eastern Shore

Home in Ocean View

4.92 out of 5 average rating, 530 reviews

Tiny House at Good Earth, near Bethany Beach

Dec 19 – 26

G$25,389 GYD per night

Cottage in Onancock

4.97 out of 5 average rating, 195 reviews

Escape to the Eastern Shore - Upscale Waterfront

Sep 1 – 8

G$37,636 GYD per night

Tiny home in Selbyville

4.98 out of 5 average rating, 211 reviews

Destination Location! Farm Animals, Tours, Beaches

Aug 31 – Sep 7

G$33,519 GYD per night

Condo in Ocean Pines

4.96 out of 5 average rating, 108 reviews

Waterview Retreat

Mar 1 – 8

G$28,903 GYD per night

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 293 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Aug 1 – 8

G$17,199 GYD per night

Farm stay in Madison

4.98 out of 5 average rating, 163 reviews

Madison Nature Getaway

Jul 11 – 18

G$25,775 GYD per night

Bungalow in Fruitland

4.93 out of 5 average rating, 112 reviews

Nana's Cottage, a place of comfort and peace

Jun 14 – 21

G$23,388 GYD per night

Apartment in Frankford

4.98 out of 5 average rating, 123 reviews

Cozy Cottage Getaway

Oct 15 – 22

G$31,095 GYD per night

Other great vacation rentals in Eastern Shore

Guest suite in Rehoboth Beach

4.98 out of 5 average rating, 122 reviews

Treetops beach getaway walkable to beach/boardwalk

Mar 27 – Apr 3

G$25,302 GYD per night

Apartment in Salisbury

4.9 out of 5 average rating, 167 reviews

Private Luxurious One Bedroom Apartment

Sep 26 – Oct 3

G$29,457 GYD per night

Home in Milton

4.99 out of 5 average rating, 189 reviews

ON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.

Mar 8 – 15

G$119,674 GYD per night

Guesthouse in Annapolis

4.9 out of 5 average rating, 207 reviews

Calico Cottage Guest House, king bed, free parking

Feb 25 – Mar 4

G$20,413 GYD per night

Home in Annapolis

4.96 out of 5 average rating, 109 reviews

Historic Downtown in-law suite

Jan 10 – 17

G$25,328 GYD per night

Cottage in Berlin

4.99 out of 5 average rating, 119 reviews

Bayfront Cottage w/ Amazing Views

Jan 24 – 31

G$34,231 GYD per night

Guest suite in Lusby

4.99 out of 5 average rating, 303 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Apr 1 – 8

G$26,664 GYD per night

Condo in Dewey Beach

4.99 out of 5 average rating, 147 reviews

DeweyBeach Condo 2BR + sleeper. Walk to the beach!

Dec 6 – 13

G$21,426 GYD per night

Destinations to explore