Search Cottages in Princess Anne

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 67 Cottages in Princess Anne with updated reviews, rates, and availability.

Key West Cottages
Exterior
Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (291)
"The Key West Cottages were beyond exceptional! The property is perfect in so many ways - the location is convenient and picturesque, the property is immaculate, well maintained and everything is like “new” condition. Units are easy to access and walkways are safe and clear. The only elevation is in the four steps to your front door! Plenty of parking, walking convenient to everything in town and restaurants, The pool and the beach area are very lovely, intimate and easily accessed. The...
The price is AED 414
AED 464 total
includes taxes & fees
24 Nov - 25 Nov
Key West Cottages
Cozy Little Cottage on chincoteague island va.
Exterior detail
Cozy Little Cottage on chincoteague island va.
9.6 out of 10, Exceptional, (35)
"The cottage is as described. There is no stove but it truly didn’t matter. Bed is very compfy. Shower is clean and hot. Quit neighborhood. The screened in porch is the best! Coffee and reading in the rockers. The cottage is close to everything !Thank you Don. We loved our stay."
Cozy Little Cottage on chincoteague island va.
Chincoteague House w/ Enclosed Porch + Deck
Living area
Chincoteague House w/ Enclosed Porch + Deck
3.0 star property
Chincoteague House w/ Enclosed Porch + Deck
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
Exterior
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
10.0 out of 10, Exceptional, (6)
"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!
Serenity Cottage: Central to state parks, historic towns, MD & VA beaches
Exterior
Serenity Cottage: Central to state parks, historic towns, MD & VA beaches
10.0 out of 10, Exceptional, (4)
"Perfect peaceful days. Everything you could ask for and more. The house is charming and spotless. Communication instantaneous. Setting so calming. Thank you so very much for sharing your home! I want to come back please."
Serenity Cottage: Central to state parks, historic towns, MD & VA beaches
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell Vacation Rental | 2BR | 1BR | 5 Steps Required | 1,476 Sq Ft
Pet-Friendly Smith Island Cottage w/ Golf Cart!
9.8 out of 10, Exceptional, (9)
"great but high tide problems to limit activity"
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
Exterior
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
9.8 out of 10, Exceptional, (275)
"Clean and quiet. Efficient use of space"
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
Pool
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
9.6 out of 10, Exceptional, (43)
"Wonderful property and great location. Would love to stay in cabin 5 again. Had everything we needed. Management was friendly and always available."
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
SeaLaVie!!!
Exterior
SeaLaVie!!!
9.8 out of 10, Exceptional, (37)
"On the island to visit family and wanted my own space! The cottage was perfect! The decor in line with the cottage theme! So clue and comfortable. It was the perfect setting. Quiet neighborhood. Even saw deer one morning!"
SeaLaVie!!!
Deal Island Bay Cottage
Sunsets at the nearby beach
Deal Island Bay Cottage
9.6 out of 10, Exceptional, (54)
"We got every year and stay here, it’s great! "
The price is AED 422
AED 794 total
includes taxes & fees
10 Nov - 11 Nov
Deal Island Bay Cottage
The Hideaway Cottage
Outdoor dining
The Hideaway Cottage
9.8 out of 10, Exceptional, (79)
"Has what you need. It is cozy. Close to town and the beach. Third time staying here. Love it. "
The Hideaway Cottage
Small cottage for those little getaways
Exterior
Small cottage for those little getaways
10.0 out of 10, Exceptional, (105)
"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
CATCHTHEWAVE!! And a discounted rate to get us started!!
Exterior
CATCHTHEWAVE!! And a discounted rate to get us started!!
10.0 out of 10, Exceptional, (7)
"Stayed here with a group of friends. 6 of us in total, plenty of room. Great house, great location, reasonably priced!"
CATCHTHEWAVE!! And a discounted rate to get us started!!
Cottage On Famous Chincoteague Island-Famous Wild Ponies
Exterior
Cottage On Famous Chincoteague Island-Famous Wild Ponies
9.8 out of 10, Exceptional, (60)
"We enjoyed our stay at this cottage. It was clean and had everything there that we needed. It was close to everything and a lot of places were walkable."
Cottage On Famous Chincoteague Island-Famous Wild Ponies
Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS
Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS
7.0 out of 10, Good, (10)
"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
1BR Snug Harbor Waterfront cottage with a lighthouse view!
Miscellaneous
1BR Snug Harbor Waterfront cottage with a lighthouse view!
9.2 out of 10, Wonderful, (7)
"Glad we were able to upgrade. More room and on the water. Smooth process all around. "
1BR Snug Harbor Waterfront cottage with a lighthouse view!
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
9.6 out of 10, Exceptional, (128)
"This house is great for small family with dogs . I had my 2 daughters , wife and 2 dogs and the house was perfect. Great condition, location, and the house Manager was great ! Always there if I had any questions and really made sure I and my family felt like home and had everything we needed . I would recommend this place to anyone and will definitely be happy to book this property in the future"
The price is AED 477
AED 1,285 total
includes taxes & fees
14 Nov - 15 Nov
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
"The 3 Sisters" Ivy's Cottage-Adorable In Town Cottage Near Historic Main Street
Outdoor dining
"The 3 Sisters" Ivy's Cottage-Adorable In Town Cottage Near Historic Main Street
10.0 out of 10, Exceptional, (2)
"The cottage is so beautiful, clean and in the best location in town. Loved that the grocery store was directly behind the cottage! The cottage has everything that you need and just beautiful. Everyone was so accommodating and so nice. We will be back next year for sure. Tha k yoj"
The price is AED 433
AED 978 total
includes taxes & fees
8 Dec - 9 Dec
"The 3 Sisters" Ivy's Cottage-Adorable In Town Cottage Near Historic Main Street
Channel View Charmer - Water Views and Pet Friendly!
Welcome to Channel View Charmer on Chincoteague Island!
Channel View Charmer - Water Views and Pet Friendly!
10.0 out of 10, Exceptional, (1)
"A nice house with a great location, easy to get to everything on the island. Having a playground across the street was extremely helpful with two small kids. Only critique was that the twin mattress were slippery enough that my kids fell out of bed. They are both on twin beds at home and we were suprised that was an issue. Other than that great!"
Channel View Charmer - Water Views and Pet Friendly!
Mae's Landing - Comfortable 2BR close to Memorial Park, NO LINENS PROVIDED
Mae's Landing - Comfortable 2BR close to Memorial Park, NO LINENS PROVIDED
9.2 out of 10, Wonderful, (16)
"Adorable little bungalow. Perfect fir a small family. Big plus is it is pet friendly. Walking distance to Memorial Park. This is our 2nd time staying, can't wait to return."
Mae's Landing - Comfortable 2BR close to Memorial Park, NO LINENS PROVIDED
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.
Don't see what you're looking for?
See all available properties in Princess Anne
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Princess Anne

Key West Cottages
Exterior
Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (291)
"The Key West Cottages were beyond exceptional! The property is perfect in so many ways - the location is convenient and picturesque, the property is immaculate, well maintained and everything is like “new” condition. Units are easy to access and walkways are safe and clear. The only elevation is in the four steps to your front door! Plenty of parking, walking convenient to everything in town and restaurants, The pool and the beach area are very lovely, intimate and easily accessed. The...
The price is AED 414
AED 464 total
includes taxes & fees
24 Nov - 25 Nov
Key West Cottages
Blufin Bungalows & Marina
Reception
Blufin Bungalows & Marina
3.0 star property
9.4 out of 10, Exceptional, (80)
"We enjoyed the floating bungalow. Nice to have somewhere different to try."
Blufin Bungalows & Marina
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
Exterior
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
9.8 out of 10, Exceptional, (275)
"Clean and quiet. Efficient use of space"
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
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.

Frequently asked questions

Why book your cottage in Princess Anne with Expedia?
We think that vacays should be a breeze, so if you’re after cottages in Princess Anne at a great price, Expedia delivers. Save money and pick a wallet-friendly option far from the downtown buzz, or splurge on a 5-star cottage to spoil your loved ones.
How can I find cheap cottages in Princess Anne?
The quickest way to track down cheap cottages in Princess Anne is with Expedia’s filter tool. Fine-tune your search results by star rating, amenities and budget to access unbeatable bargains in a couple of clicks.