Search Cottages in Princess Anne

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Cottages in Princess Anne

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (404)
"We had wonderful stay. Everything about this resort was perfect. "
Key West Cottages

The Hideaway Cottage

9.8 out of 10, Exceptional, (86)
"Convenient location! Exactly as advertised!"
The Hideaway Cottage

Cozy Little Cottage on chincoteague island va.

9.6 out of 10, Exceptional, (40)
"Very cute little cottage, perfect amount of space for 2, has just about everything you'd need! Owner is helpful as well. Lots of places to eat within 15 mins"
Cozy Little Cottage on chincoteague island va.

1BR Waterfront cottage with a view of the wild Chincoteague ponies!

9.4 out of 10, Exceptional, (9)
"Great location, very clean and amazing staff. I highly recommend staying here."
1BR Waterfront cottage with a view of the wild Chincoteague ponies!

Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

9.4 out of 10, Exceptional, (131)
"Awesome two night stay! Highly recommend! "
The price is AED 1,717
AED 2,619 total
includes taxes & fees
16 Jul - 17 Jul
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

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

10.0 out of 10, Exceptional, (7)
"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

Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED

9.6 out of 10, Exceptional, (24)
"Vacation very enjoyable and peaceful"
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED

Small cottage for those little getaways

10.0 out of 10, Exceptional, (109)
"Very cozy cottage tucked off the road great check-in experience place was clean easy parking will definitely go back again"
Small cottage for those little getaways

Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

10.0 out of 10, Exceptional, (11)
"The house was tidy and clean, and had everything our family needed. The playground and pickleball courts next door were a plus for us! The easy walk to shops on Main Street was also nice. "
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS

7.0 out of 10, Good, (13)
"The Salty Sailor was an excellent, affordable, and pet friendly rental. Nice location on ridge rd next to Mr Baldys which is a must to try if you stay here. The rooms are a bit older but maintained well. I didn’t experience any of the conditions that were listed in the other reviews here. We would certainly stay here again."
Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS

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

10.0 out of 10, Exceptional, (16)
"Took my grandson for a weekend trip to Smith Island to celebrate his HS graduation. My daughter, also, accompanied us, since I am a 90 year old "Grammy", and need some assistance. Our cottage was clean, comfortable and had all of our needs. The host, Kim, was extremely attentive, and made our dinner the night we arrived so we could just relax. I would highly recommend Idle Hour as the place to stay on Smith Island. Pat Reynolds, Ellicott City, MD"
The price is AED 643
AED 1,176 total
includes taxes & fees
3 Aug - 4 Aug
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

COTTAGE BLUEFISH on Chincoteague Island! A cozy island getaway -NEW REMODEL

10.0 out of 10, Exceptional, (9)
"A small, cozy and quiet cottage that is a perfect getaway. Coastal decor is perfect and several outside living areas offer multiple options to enjoy the beautiful yard. Easy access to downtown, shops and the gorgeous beach or pony viewing. The hosts are super responsive to any questions and we can't wait to return."
COTTAGE BLUEFISH on Chincoteague Island! A cozy island getaway -NEW REMODEL

6 Mi to Salisbury: Forest-view Sanctuary!

3.0 star property
6 Mi to Salisbury: Forest-view Sanctuary!

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (8)
"Beautiful sunset views and well accommodating house. "
Waterfront Maryland Retreat w/ Dock & Bay View!

Chincoteague House w/ Enclosed Porch + Deck

3.0 star property
Chincoteague House w/ Enclosed Porch + Deck

NEW PET FRIENDLY LISTING ALERT!!

9.4 out of 10, Exceptional, (8)
"Lovely home right on the river- fishing to your hearts content Clean, lots to do very peaceful!!! Would definitely come back! Mia is great to work with"
NEW PET FRIENDLY LISTING ALERT!!

2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

9.6 out of 10, Exceptional, (44)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Pet-Friendly Smith Island Cottage w/ Golf Cart!

10.0 out of 10, Exceptional, (17)
"The island is a beautiful and peaceful. Everyone there is so friendly and helpful. The cottage was a very clean and comfortable place to stay. We had 3 adults and 2 huskies and the home was very spacious. It is close to the docks, restaurant, and grocery store. We enjoyed our stay. If you’re looking for a peaceful and relaxing getaway this is the place to go! "
Pet-Friendly Smith Island Cottage w/ Golf Cart!

Chincoteague Island Cottage ~ 2 Mi to Beaches

3.0 star property
10.0 out of 10, Exceptional, (1)
"Property was great and it is very close to the beach area as well as the wild ponies. Walkable to all the coffee shops and ice cream. Only downside, if you cook there is nothing locally good to eat but won’t hold it against the area, just preference. People were great and coffee shops were great. "
Chincoteague Island Cottage ~ 2 Mi to Beaches
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Why book your cottage in Princess Anne with Expedia?
We think a getaway should be a piece of cake, so if you're chasing cottages in Princess Anne at a competitive price, Expedia has you covered. Save money and choose a cheap option far from the rush of the city, or splurge on a luxury cottage to pamper your favorite people.
How can I find cheap cottages in Princess Anne?
Expedia can help you track down cheap cottages in Princess Anne. To lock in the perfect stay in just a few keystrokes, simply use our convenient filter tool to refine your search results by star rating, budget and amenities.