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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Cottages in Crisfield

Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Aerial view

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
Property grounds

Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

10.0 out of 10, Exceptional, (7)
"The place is amazing. The pictures on the site do not do the property justice as it is absolutely amazing. Can’t wait to stay there again."
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
Charming Cottage - Ultimate Relaxation Destination
Exterior

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (117)
"I had stayed at this property in the past and was really glad to get to stay again. It is clean, quiet, and close to the town center of Onancock. Really looking forward to returning!"
Charming Cottage - Ultimate Relaxation Destination
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Exterior

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

10.0 out of 10, Exceptional, (15)
"Micky and Kim were great hosts and the house was awesome. They were very accommodating. Will definitely be back! "
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Miscellaneous

Pet-Friendly Smith Island Cottage w/ Golf Cart!

10.0 out of 10, Exceptional, (14)
"great but high tide problems to limit activity"
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Unique Tangier Cottage w/ Chesapeake Bay Views!
Fridge, microwave, oven, stovetop

Unique Tangier Cottage w/ Chesapeake Bay Views!

10.0 out of 10, Exceptional, (7)
"Lovely home with great set up for our stay"
Unique Tangier Cottage w/ Chesapeake Bay Views!
Beautiful, Waterfront, Luxury
Terrace/patio

Beautiful, Waterfront, Luxury

10.0 out of 10, Exceptional, (4)
"Great place for a weekend away - house was beautiful and hosts were always quick to answer"
Beautiful, Waterfront, Luxury
ESVA Down by the Sea & Pet Friendly
Exterior

ESVA Down by the Sea & Pet Friendly

9.6 out of 10, Exceptional, (5)
"Very nice place. Located in a great spot for our needs. First thing we noticed was how clean it was. I will definitely book this again on our next trip to ESVA!"
ESVA Down by the Sea & Pet Friendly
Waterfront Maryland Retreat w/ Dock & Bay View!
Beach

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (6)
"Beautiful sunset views and well accommodating house. "
Waterfront Maryland Retreat w/ Dock & Bay View!
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly
Outdoor dining

Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

9.4 out of 10, Exceptional, (19)
"Perfect base to go out and explore and fish the Chesapeake. "
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly
Serenity Cottage: Central to state parks, historic towns, MD & VA beaches
Fridge, microwave, oven, stovetop

Serenity Cottage: Central to state parks, historic towns, MD & VA beaches

10.0 out of 10, Exceptional, (6)
"Great location close to main road but quiet and removed from the busy tourist area of the island. Clean property with all the necessities. Quick and easy communication with property manager.."
Serenity Cottage: Central to state parks, historic towns, MD & VA beaches
Dog-Friendly Westover Cottage w/ River Access!
Fridge, microwave, stovetop, dishwasher

Dog-Friendly Westover Cottage w/ River Access!

9.8 out of 10, Exceptional, (10)
"We had a great stay at the cottage with our kids & dogs. The cottage was well-appointed, with the full kitchen so we did a few crab boils - excellent! Paddled up and down the Big Annemessex River, very peaceful, lots of birds and wildlife to observe. It's a beautiful spot."
Dog-Friendly Westover Cottage w/ River Access!
Blue Heron Cottage On Smith's Island
Beach

Blue Heron Cottage On Smith's Island

9.8 out of 10, Exceptional, (38)
"The stay was just perfect. We came with our own boat and it was easy to navigate to the house. The dock was 30 yards from the front door so easy to get out supplies to the house. (We did make use of the golf cart 😊). Neighbors are so friendly and they let us use their phone to call our family to let them know we arrived. Our cell phones did not work as it is a bit remote. We later found out that there is some coverage on the second floor of the house😁 Nevertheless we did not miss internet and...
Blue Heron Cottage On Smith's Island
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
Interior

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Osprey House was the perfect location for our getaway! The owners were amazing and the house was gorgeous! The view from the back yard was exactly what we needed after a long day at a wrestling tournament! "
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
Unique Tangier Cottage w/ Chesapeake Bay Views!
Interior

Unique Tangier Cottage w/ Chesapeake Bay Views!

3.0 star property
Unique Tangier Cottage w/ Chesapeake Bay Views!
Pet-friendly Smith Island Cottage w/ Golf Cart!
Miscellaneous

Pet-friendly Smith Island Cottage w/ Golf Cart!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
Pet-friendly Smith Island Cottage w/ Golf Cart!
Dog-friendly Westover Cottage w/ River Access!
Cottage (2 Bedrooms) | Front of property

Dog-friendly Westover Cottage w/ River Access!

3.0 star property
8.0 out of 10, Very Good, (1)
"It was great and family enjoyed our relaxation "
Dog-friendly Westover Cottage w/ River Access!
'Cora's Cottage' Near Chesapeake Bay Access!
Beach

'Cora's Cottage' Near Chesapeake Bay Access!

10.0 out of 10, Exceptional, (2)
"House was very clean and comfortable. Great spot for a family with young adults. Nice bike ride or walk to the beautiful water area. "
'Cora's Cottage' Near Chesapeake Bay Access!
11 Mi to Chincoteague: Atlantic Home w/ Decks!
Property grounds

11 Mi to Chincoteague: Atlantic Home w/ Decks!

3.0 star property
11 Mi to Chincoteague: Atlantic Home w/ Decks!
1 Mi to Boat Ramp: Peaceful Deal Island Home!
Outdoor dining

1 Mi to Boat Ramp: Peaceful Deal Island Home!

3.0 star property
1 Mi to Boat Ramp: Peaceful Deal Island Home!
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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