Assateague Island vacation rentals
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Top-rated vacation rentals in Assateague Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Condo in Berlin
4.98 out of 5 average rating, 103 reviewsAmazing 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
Tiny home in Accomac
4.93 out of 5 average rating, 437 reviewsLittle 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
Condo in Ocean Pines
4.96 out of 5 average rating, 102 reviewsPeaceful 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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Assateague Island vacation rentals
Assateague Island beach vacation rentals
Home in Chincoteague
4.94 out of 5 average rating, 284 reviewsSeas the Day Getaway~Pool ~near Waterfront Park
Jan 23 – 30
Cottage in Westover
4.99 out of 5 average rating, 178 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Dec 7 – 14
Condo in Ocean City
4.91 out of 5 average rating, 174 reviews**Beautiful newly renovated OC MD water view home*
Apr 23 – 30
Guest suite in Chincoteague
4.93 out of 5 average rating, 218 reviewsBaywatch North-Waterfront & Roaming Ponies
Aug 11 – 18
Townhouse in Ocean City
4.97 out of 5 average rating, 343 reviewsEdgewater Escape - Bayfront Condo w/Private Porch
Jul 20 – 27
Condo in Ocean City
4.94 out of 5 average rating, 206 reviewsAwesome mid-town OC Location! Steps to the Beach!
Dec 16 – 23
Cottage in Ocean City
4.94 out of 5 average rating, 126 reviewsPET FRIENDLY! BEACHY GETAWAY COTTAGE-WEST OCMD
Oct 22 – 29
Cottage in Chincoteague
4.94 out of 5 average rating, 110 reviewsPony Pines!Your Waterfront Getaway Cottage Awaits!
Nov 24 – Dec 1
Condo in Ocean City
4.87 out of 5 average rating, 139 reviewsUnit 7 on 41 St Ocean Side 50 steps to beach
Nov 25 – Dec 2
Condo in Ocean City
4.89 out of 5 average rating, 163 reviews🌊Oceanfront studio w/ amazing views & amenities🏖
Apr 8 – 15
Cottage in Chincoteague
4.98 out of 5 average rating, 127 reviewsWaterfront-CI Bay sunsets-Amazing views
Mar 6 – 13
Home in Crisfield
4.95 out of 5 average rating, 252 reviewsCozy Home near Waterfront in Crisfield, MD
Jul 3 – 10
Assateague Island house rentals
Home in Accomac
4.98 out of 5 average rating, 216 reviewsHeartsong Farmhouse , a nature lover's retreat.
Sep 27 – Oct 4
Home in Parsonsburg
4.83 out of 5 average rating, 115 reviewsForest Grove Retreat
Nov 17 – 24
Home in Ocean View
4.91 out of 5 average rating, 529 reviewsTiny House at Good Earth, near Bethany Beach
Nov 1 – 8
Home in Chincoteague
4.96 out of 5 average rating, 125 reviewsCharming Island Home "Sandy Pines"
May 5 – 12
Home in Reedville
4.97 out of 5 average rating, 115 reviewsSunkissed Cottage-private, natural waterfront home
Sep 6 – 13
Home in Berlin
4.78 out of 5 average rating, 174 reviewsOC, Md great amenities in community, near beaches
Aug 17 – 24
Home in Cambridge
4.92 out of 5 average rating, 176 reviewsGuest House: Farm homestead
Jul 3 – 10
Home in Chincoteague Island
4.92 out of 5 average rating, 184 reviewsWe’ve Thought of Everything So You Can Relax!
Aug 10 – 17
Home in Rehoboth Beach
4.79 out of 5 average rating, 614 reviewsContemporary 1 Bedroom 2 level home
Feb 10 – 17
Home in Onancock
4.8 out of 5 average rating, 116 reviewsCharming Waterfront Cottage on Cedar Creek
Mar 5 – 12
Home in Ocean View
4.87 out of 5 average rating, 439 reviewsPrivate place near Bethany Beach
Nov 11 – 18
Home in Reedville
4.96 out of 5 average rating, 202 reviewsWaterfront FamilyFriendly Home Improved for 2023
Feb 6 – 13
Assateague Island condo rentals
Condo in Ocean City
4.82 out of 5 average rating, 124 reviews1 BR Ocean Block (Unit 17) 40th St Midtown OC
Oct 11 – 18
Condo in Ocean City
4.94 out of 5 average rating, 160 reviewsGorgeous Oceanfront Condo- Beach, Pool, Hot Tub!
Sep 20 – 27
Condo in Ocean City
4.89 out of 5 average rating, 151 reviewsPrime Condo North OC 2 Blocks to Beach w/ Pool
Apr 1 – 8
Condo in Ocean City
4.99 out of 5 average rating, 106 reviewsCozy & Clean Condo on 36th st. Steps to Beach!
Mar 7 – 14
Condo in Ocean City
4.9 out of 5 average rating, 114 reviewsA Serene Beachfront Getaway - 2 BR St. Tropez OC!
Apr 8 – 15
Condo in Ocean City
4.95 out of 5 average rating, 190 reviewsCaramar Couples Retreat
Apr 29 – May 6
Condo in Dewey Beach
4.99 out of 5 average rating, 143 reviewsDeweyBeach Condo 2BR + sleeper. Walk to the beach!
Oct 29 – Nov 5
Condo in Ocean City
4.95 out of 5 average rating, 221 reviewsNice 2 BR Oceanfront, Year Round Fun & Amenities!
Jan 17 – 24
Condo in Ocean City
4.88 out of 5 average rating, 138 reviewsOcean Front Sea Terrace 209 Heated Pool
Oct 31 – Nov 7
Condo in Ocean City
4.84 out of 5 average rating, 306 reviews🌊 NOTHING BEATS OCEANFRONT!!! 🌊
Apr 25 – May 2
Condo in Ocean City
4.99 out of 5 average rating, 178 reviewsCozy oceanfront condo with stunning ocean views
May 29 – Jun 5
Condo in Ocean City
4.92 out of 5 average rating, 116 reviewsBeach Baby Ocean Block Studio-Mid Town-All U Need
Feb 5 – 12
Destinations to explore
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- Rentals with pools Assateague Island
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