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

G$39,637 GYD 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!

Aug 16 – 23

G$24,854 GYD per night
Guest favorite

Condo in Ocean Pines

4.96 out of 5 average rating, 102 reviews

Peaceful Water View Retreat

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Feb 28 – Mar 7

G$29,018 GYD 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, 284 reviews

Seas the Day Getaway~Pool ~near Waterfront Park

Jan 23 – 30

G$42,983 GYD per night
Guest favorite

Cottage in Westover

4.99 out of 5 average rating, 178 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Dec 7 – 14

G$70,489 GYD 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

G$20,107 GYD per night
Guest favorite

Guest suite in Chincoteague

4.93 out of 5 average rating, 218 reviews

Baywatch North-Waterfront & Roaming Ponies

Aug 11 – 18

G$46,806 GYD 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

G$128,968 GYD 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

G$21,712 GYD 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

G$29,244 GYD per night
Guest favorite

Cottage in Chincoteague

4.94 out of 5 average rating, 110 reviews

Pony Pines!Your Waterfront Getaway Cottage Awaits!

Nov 24 – Dec 1

G$61,988 GYD 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

G$15,868 GYD 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

G$29,093 GYD per night
Guest favorite

Cottage in Chincoteague

4.98 out of 5 average rating, 127 reviews

Waterfront-CI Bay sunsets-Amazing views

Mar 6 – 13

G$62,282 GYD per night
Guest favorite

Home in Crisfield

4.95 out of 5 average rating, 252 reviews

Cozy Home near Waterfront in Crisfield, MD

Jul 3 – 10

G$33,453 GYD 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 27 – Oct 4

G$32,856 GYD per night
Guest favorite

Home in Parsonsburg

4.83 out of 5 average rating, 115 reviews

Forest Grove Retreat

Nov 17 – 24

G$24,405 GYD 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

G$25,490 GYD per night
Guest favorite

Home in Chincoteague

4.96 out of 5 average rating, 125 reviews

Charming Island Home "Sandy Pines"

May 5 – 12

G$57,981 GYD per night
Guest favorite

Home in Reedville

4.97 out of 5 average rating, 115 reviews

Sunkissed Cottage-private, natural waterfront home

Sep 6 – 13

G$30,883 GYD 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

G$42,660 GYD per night
Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 176 reviews

Guest House: Farm homestead

Jul 3 – 10

G$26,095 GYD per night
Guest favorite

Home in Chincoteague Island

4.92 out of 5 average rating, 184 reviews

We’ve Thought of Everything So You Can Relax!

Aug 10 – 17

G$66,238 GYD per night
Superhost

Home in Rehoboth Beach

4.79 out of 5 average rating, 614 reviews

Contemporary 1 Bedroom 2 level home

Feb 10 – 17

G$25,599 GYD per night
Guest favorite

Home in Onancock

4.8 out of 5 average rating, 116 reviews

Charming Waterfront Cottage on Cedar Creek

Mar 5 – 12

G$46,477 GYD per night
Guest favorite

Home in Ocean View

4.87 out of 5 average rating, 439 reviews

Private place near Bethany Beach

Nov 11 – 18

G$23,287 GYD per night
Guest favorite

Home in Reedville

4.96 out of 5 average rating, 202 reviews

Waterfront FamilyFriendly Home Improved for 2023

Feb 6 – 13

G$33,895 GYD per night

Assateague Island condo rentals

Guest favorite

Condo in Ocean City

4.82 out of 5 average rating, 124 reviews

1 BR Ocean Block (Unit 17) 40th St Midtown OC

Oct 11 – 18

G$27,833 GYD per night
Guest favorite

Condo in Ocean City

4.94 out of 5 average rating, 160 reviews

Gorgeous Oceanfront Condo- Beach, Pool, Hot Tub!

Sep 20 – 27

G$65,023 GYD 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

Apr 1 – 8

G$23,972 GYD 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!

Mar 7 – 14

G$36,159 GYD 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

G$33,214 GYD per night
Guest favorite

Condo in Ocean City

4.95 out of 5 average rating, 190 reviews

Caramar Couples Retreat

Apr 29 – May 6

G$38,800 GYD per night
Guest favorite

Condo in Dewey Beach

4.99 out of 5 average rating, 143 reviews

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

Oct 29 – Nov 5

G$28,901 GYD 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!

Jan 17 – 24

G$39,203 GYD 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

G$35,332 GYD per night
Superhost

Condo in Ocean City

4.84 out of 5 average rating, 306 reviews

🌊 NOTHING BEATS OCEANFRONT!!! 🌊

Apr 25 – May 2

G$27,129 GYD 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

G$52,693 GYD 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

Feb 5 – 12

G$42,090 GYD per night

Destinations to explore