Holiday Homes in Assateague Island

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Assateague Island and around

Blufin Bungalows & Marina
Relax in a serene waterfront retreat with enclosed balconies and a tranquil atmosphere.

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (157)
"excellent place to stay on the water"
Blufin Bungalows & Marina
Sunset Island is Loved for it's Amazing Amenities
Relax by the pool surrounded by lounge chairs and umbrellas, with a gazebo and ocean views.

Sunset Island is Loved for it's Amazing Amenities

Sunset Island is Loved for it's Amazing Amenities
Waterfront home, managed privately with lower fees. Close to DE and OC Beaches.
Enjoy cooking in this well-equipped kitchen with a central island, oven, and ample cabinetry.

Waterfront home, managed privately with lower fees. Close to DE and OC Beaches.

9.8 out of 10, Exceptional, (37)
"Great stay"
Waterfront home, managed privately with lower fees. Close to DE and OC Beaches.
Spacious 4-bedroom house in charming Ocean View with Pool! Minutes from Bethany!
Smart TV

Spacious 4-bedroom house in charming Ocean View with Pool! Minutes from Bethany!

10.0 out of 10, Exceptional, (2)
"Awesome"
Spacious 4-bedroom house in charming Ocean View with Pool! Minutes from Bethany!
At the Water's Edge - is there anywhere you'd rather be?!
Enjoy a peaceful retreat with a balcony overlooking a serene lake or river, featuring a seating area with a table and chairs.

At the Water's Edge - is there anywhere you'd rather be?!

10.0 out of 10, Exceptional, (48)
"Great property! Very clean"
At the Water's Edge - is there anywhere you'd rather be?!
Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and sink.

Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool

9.8 out of 10, Exceptional, (43)
"This is a nice property located a short drive or "
Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
Beautiful 3 BR 2.5 BA New Home in West Ocean City's Bayside Community
Enjoy meals in the kitchen with a stove, oven, and dining area.

Beautiful 3 BR 2.5 BA New Home in West Ocean City's Bayside Community

10.0 out of 10, Exceptional, (7)
Beautiful 3 BR 2.5 BA New Home in West Ocean City's Bayside Community
Downtown Perch W/ Free WiFi, Private Balcony/Patio, Easy Beach Access & More
Overlooking a wide sandy beach, this property offers stunning views of the calm sea.

Downtown Perch W/ Free WiFi, Private Balcony/Patio, Easy Beach Access & More

9.4 out of 10, Exceptional, (19)
"Well cared for"
Downtown Perch W/ Free WiFi, Private Balcony/Patio, Easy Beach Access & More
Bayfront Community with private beach, boat slip, and pool.
Residents enjoy scenic views of a central water body from their homes in this peaceful neighborhood.

Bayfront Community with private beach, boat slip, and pool.

9.8 out of 10, Exceptional, (51)
"Nice area, quite, enjoyed our vacation!"
Bayfront Community with private beach, boat slip, and pool.
Wave Watcher's Condo - Steps to the beach!
Relax in a spacious living area with a sofa and dining table, featuring a washer and dryer.

Wave Watcher's Condo - Steps to the beach!

9.8 out of 10, Exceptional, (7)
"The place was very clean and very cool, which was nice on the hot days. Some of my party slept on the floor so I'd say it sleeps 10 but overall, wonderful place would recommend to anyone!"
Wave Watcher's Condo - Steps to the beach!
Bear Trap Dunes townhome with central AC & washer/dryer - on-site pools & tennis
Prepare meals in the spacious kitchen with a large island and dining area for family meals.

Bear Trap Dunes townhome with central AC & washer/dryer - on-site pools & tennis

9.2 out of 10, Wonderful, (24)
"The house was comfortable, cozy and clean. We enjoyed relaxing with friends and family while there. It’s a very open floor plan with the master downstairs and two more bedrooms upstairs."
Bear Trap Dunes townhome with central AC & washer/dryer - on-site pools & tennis
Bethany Beach and Close by Marinas! Family and Pet Friendly!!
Enjoy sunbathing and relaxation in a beach area with umbrellas and ocean views.

Bethany Beach and Close by Marinas! Family and Pet Friendly!!

9.2 out of 10, Wonderful, (76)
"Stayed with friends, great location. Comfortable!"
The price is €440
includes taxes & fees
5 Aug - 6 Aug
Bethany Beach and Close by Marinas! Family and Pet Friendly!!
Congratulations! You have found one of the Best Vacation Homes in Fenwick
Enjoy cooking in this well-equipped kitchen with a microwave, oven, and granite countertop.

Congratulations! You have found one of the Best Vacation Homes in Fenwick

9.8 out of 10, Exceptional, (95)
"House was great. Very nice and clean. No complaints at all. "
Congratulations! You have found one of the Best Vacation Homes in Fenwick
Beach Cove: Ocean Front 4Bed/2Bath - Ocean City MD
Relax on the deck with comfortable seating and dining areas overlooking the beach.

Beach Cove: Ocean Front 4Bed/2Bath - Ocean City MD

9.6 out of 10, Exceptional, (44)
"Highly recommend and will surly book again"
Beach Cove: Ocean Front 4Bed/2Bath - Ocean City MD
Family fun! Beach, Kayaking, yard games, large fenced yard, fire pit. 2 mi beach
Enjoy the serene beach scene with gentle waves and fine sand.

Family fun! Beach, Kayaking, yard games, large fenced yard, fire pit. 2 mi beach

10.0 out of 10, Exceptional, (55)
"love it here!!"
Family fun! Beach, Kayaking, yard games, large fenced yard, fire pit. 2 mi beach
Bayside escape with pools, golf, tennis, fishing, spas & saunas + beach shuttle
Fully equipped kitchen with a marble countertop and white tiled floor.

Bayside escape with pools, golf, tennis, fishing, spas & saunas + beach shuttle

9.2 out of 10, Wonderful, (12)
"We love Bayside Resort. This house was perfect for our family’s needs. They included nice amenities like dog bowls and kids books. Love Bayside’s pool and the kayaks on Assawoman Bay."
Bayside escape with pools, golf, tennis, fishing, spas & saunas + beach shuttle
Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes
Fridge, microwave, oven, stovetop

Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes

8.0 out of 10, Very good, (2)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We were two families with children is different age groups. Everyone of us were comfortable in the property. Had a pleasant stay when not in the beach. All amenities were intact and suffice for a comfortable stay. OC beach is 30 minutes away and...
Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes
PARTIAL WEEK AVAILABLE - Amazing views! Professionally designed Improvements!
Enjoy serene waterfront views from this tranquil retreat.

PARTIAL WEEK AVAILABLE - Amazing views! Professionally designed Improvements!

9.6 out of 10, Exceptional, (134)
"Our group of six really enjoyed our stay!"
PARTIAL WEEK AVAILABLE - Amazing views! Professionally designed Improvements!
Bethany Beach New Castle 4BR 2BA Canal Front Home
TV, offices

Bethany Beach New Castle 4BR 2BA Canal Front Home

9.4 out of 10, Exceptional, (3)
"The beach house was so cute and short distance from the beach. It had everything we needed ! The hosts were very nice and ready to help "
Bethany Beach New Castle 4BR 2BA Canal Front Home
Oceanblock, steps to best beach in Bethany
Relax in this stylish living room with a ceiling fan, flat-screen TV, and wicker sofa.

Oceanblock, steps to best beach in Bethany

9.4 out of 10, Exceptional, (52)
"The property was well located and well appointed. Everything we had was at our fingertips. We would certainly stay here again and recommend to others."
Oceanblock, steps to best beach in Bethany
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Assateague Island Hotel Reviews

Fenwick Inn

Fenwick Inn

10/10 Excellent
"unfortunately we were placed beside a room that had yippy dogs that barked all day and most of the night. We actually talked to front desk while their to report that the people were gone all day and never took there poor dog out! "
Tegan 5-night trip
Posted 19 hours ago
Fenwick Inn