Assateague Island vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Assateague Island

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

Guest favorite

Condo in Berlin

4.98 out of 5 average rating, 103 reviews

Amazing Waterfront in Berlin, MD- Sea Breeze Suite

1 of 5 waterfront units (Drift Inn, Sea Breeze, Coconut Grove, Coral Tides, Day Break) located at The Inn on Turville Creek in West Ocean City. Perfect for outdoor lovers or a quiet escape. Bring your paddleboards, kayaks, or just enjoy the beautiful views from the comfort of your own patio. The Inn is located approximately 5 miles from downtown Ocean City and the town of Berlin, MD (voted America's Coolest Small Town) and ~10 miles from Assateague. Stunning sunsets right from your front patio!

Oct 25 – Nov 1

$165 per night
Guest favorite

Tiny home in Accomac

4.93 out of 5 average rating, 437 reviews

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a tiny house with big charm. This rural cottage on a 50 acre farm is nestled between peaceful fields, woods, marsh and creek. Curated with hygge comfort and efficiency in mind, you'll love the natural light and serene decor. • Epic stargazing • Heavenly private outdoor shower • Firepit with wood provided • Ample open spaces • Peace and quiet for sleeping • Comfy patio seating for chilling, coffee, and cocktails • Fast Starlink WIFI. • Proud Superhost for 10+ years!

Oct 7 – 14

$103 per night
Guest favorite

Tiny home in Snow Hill

4.89 out of 5 average rating, 224 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.

Jun 11 – 18

$108 per night

Popular amenities for Assateague Island vacation rentals

Assateague Island beach vacation rentals

Guest favorite

Home in Chincoteague

4.94 out of 5 average rating, 282 reviews

Seas the Day Getaway~Pool ~near Waterfront Park

Feb 21 – 28

$179 per night
Guest favorite

Condo in Ocean City

4.91 out of 5 average rating, 174 reviews

**Beautiful newly renovated OC MD water view home*

Apr 23 – 30

$83 per night
Guest favorite

Condo in Ocean City

4.94 out of 5 average rating, 206 reviews

Awesome mid-town OC Location! Steps to the Beach!

Dec 16 – 23

$90 per night
Guest favorite

Townhouse in Ocean City

4.97 out of 5 average rating, 343 reviews

Edgewater Escape - Bayfront Condo w/Private Porch

Jul 20 – 27

$537 per night
Guest favorite

Cottage in Ocean City

4.94 out of 5 average rating, 126 reviews

PET FRIENDLY! BEACHY GETAWAY COTTAGE-WEST OCMD

Oct 22 – 29

$120 per night
Guest favorite

Cottage in Chincoteague

4.94 out of 5 average rating, 110 reviews

Pony Pines!Your Waterfront Getaway Cottage Awaits!

Oct 4 – 11

$259 per night
Guest favorite

Condo in Ocean City

4.87 out of 5 average rating, 139 reviews

Unit 7 on 41 St Ocean Side 50 steps to beach

Nov 25 – Dec 2

$64 per night
Guest favorite

Condo in Ocean City

4.92 out of 5 average rating, 116 reviews

Beach Baby Ocean Block Studio-Mid Town-All U Need

Apr 16 – 23

$114 per night
Superhost

Condo in Ocean City

4.89 out of 5 average rating, 163 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

Apr 8 – 15

$120 per night
Guest favorite

Cottage in Chincoteague

4.98 out of 5 average rating, 127 reviews

Waterfront-CI Bay sunsets-Amazing views

Feb 15 – 22

$267 per night
Guest favorite

Home in Crisfield

4.95 out of 5 average rating, 252 reviews

Cozy Home near Waterfront in Crisfield, MD

Mar 19 – 26

$140 per night
Superhost

Condo in Ocean City

4.83 out of 5 average rating, 133 reviews

Romantic Beach Inscape-Best Ocean View+Heated Pool

Feb 8 – 15

$122 per night

Assateague Island house rentals

Guest favorite

Home in Accomac

4.98 out of 5 average rating, 216 reviews

Heartsong Farmhouse , a nature lover's retreat.

Sep 30 – Oct 7

$136 per night
Guest favorite

Home in Parsonsburg

4.83 out of 5 average rating, 115 reviews

Forest Grove Retreat

Dec 22 – 29

$101 per night
Guest favorite

Home in Chincoteague

4.96 out of 5 average rating, 125 reviews

Charming Island Home "Sandy Pines"

May 5 – 12

$240 per night
Guest favorite

Home in Ocean View

4.91 out of 5 average rating, 529 reviews

Tiny House at Good Earth, near Bethany Beach

Nov 1 – 8

$105 per night
Guest favorite

Home in Berlin

4.78 out of 5 average rating, 174 reviews

OC, Md great amenities in community, near beaches

Aug 17 – 24

$177 per night
Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 176 reviews

Guest House: Farm homestead

Jul 3 – 10

$109 per night
Guest favorite

Home in Chincoteague Island

4.92 out of 5 average rating, 183 reviews

We’ve Thought of Everything So You Can Relax!

Mar 7 – 14

$275 per night
Guest favorite

Home in Ocean View

4.87 out of 5 average rating, 439 reviews

Private place near Bethany Beach

Nov 10 – 17

$96 per night
Guest favorite

Home in Onancock

4.8 out of 5 average rating, 116 reviews

Charming Waterfront Cottage on Cedar Creek

Mar 12 – 19

$199 per night
Superhost

Home in Rehoboth Beach

4.79 out of 5 average rating, 614 reviews

Contemporary 1 Bedroom 2 level home

Nov 20 – 27

$123 per night
Superhost

Home in Ocean Pines

4.88 out of 5 average rating, 113 reviews

Tortuga Cottage: Your All- Season Getaway

Aug 31 – Sep 7

$233 per night
Guest favorite

Home in Salisbury

4.98 out of 5 average rating, 145 reviews

Salisbury Cottage

Jan 8 – 15

$133 per night

Assateague Island condo rentals

Guest favorite

Condo in Ocean Pines

4.96 out of 5 average rating, 102 reviews

Peaceful Water View Retreat

Oct 16 – 23

$144 per night
Guest favorite

Condo in Ocean City

4.89 out of 5 average rating, 151 reviews

Prime Condo North OC 2 Blocks to Beach w/ Pool

Feb 14 – 21

$60 per night
Guest favorite

Condo in Ocean City

4.94 out of 5 average rating, 160 reviews

Gorgeous Oceanfront Condo- Beach, Pool, Hot Tub!

Feb 12 – 19

$270 per night
Guest favorite

Condo in Ocean City

4.97 out of 5 average rating, 219 reviews

Direct Oceanfront with a View and Amenities Galore

Oct 13 – 20

$189 per night
Guest favorite

Condo in Ocean City

4.9 out of 5 average rating, 114 reviews

A Serene Beachfront Getaway - 2 BR St. Tropez OC!

Apr 8 – 15

$139 per night
Guest favorite

Condo in Ocean City

4.99 out of 5 average rating, 106 reviews

Cozy & Clean Condo on 36th st. Steps to Beach!

Jan 4 – 11

$150 per night
Guest favorite

Condo in Ocean City

4.95 out of 5 average rating, 190 reviews

Caramar Couples Retreat

May 9 – 16

$161 per night
Guest favorite

Condo in Ocean City

4.88 out of 5 average rating, 138 reviews

Ocean Front Sea Terrace 209 Heated Pool

Oct 31 – Nov 7

$145 per night
Superhost

Condo in Ocean City

4.84 out of 5 average rating, 306 reviews

🌊 NOTHING BEATS OCEANFRONT!!! 🌊

Apr 25 – May 2

$112 per night
Guest favorite

Condo in Ocean City

4.95 out of 5 average rating, 221 reviews

Nice 2 BR Oceanfront, Year Round Fun & Amenities!

Nov 4 – 11

$175 per night
Guest favorite

Condo in Lewes

4.95 out of 5 average rating, 270 reviews

Walk Downtown * Bike to Beach * Explore Cape

Dec 25 – Jan 1

$132 per night
Guest favorite

Condo in Ocean City

4.99 out of 5 average rating, 178 reviews

Cozy oceanfront condo with stunning ocean views

May 29 – Jun 5

$219 per night

Destinations to explore