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Aug 15 - Aug 17
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Cottages in Princess Anne

Key West Cottages
Situated on a wooden dock, this house offers serene waterfront views from its balcony.

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (416)
"Key West Cottages is absolutely wonderful!"
$242 nightly
The price is $272
Sep 1 - Sep 2
Total includes taxes and fees
Key West Cottages
The Hideaway Cottage
Relax on the beach with two comfortable chairs, perfect for taking in the ocean views.

The Hideaway Cottage

9.8 out of 10, Exceptional, (89)
"Convenient location! Exactly as advertised!"
The Hideaway Cottage
Cozy Little Cottage on chincoteague island va.
Escape to a serene cabin surrounded by nature, with a porch and a tranquil lawn.

Cozy Little Cottage on chincoteague island va.

9.6 out of 10, Exceptional, (44)
"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!
Relax by the serene waterfront, where kayaks line the shore and Adirondack chairs invite you to unwind.

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

9.4 out of 10, Exceptional, (10)
"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
Stunning two-story home with a charming front entrance and beautifully manicured lawn.

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

9.4 out of 10, Exceptional, (132)
"Awesome two night stay! Highly recommend! "
$531 nightly
The price is $584
Sep 3 - Sep 4
Total includes taxes and fees
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Serenity Cottage: Central to state parks, historic towns, MD & VA beaches
Enjoy a serene and stay in this single-story house surrounded by a well-maintained lawn and mature trees.

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

10.0 out of 10, Exceptional, (11)
"This property was perfectly located in between Chincoteague Island and Janes Island State Park which were both destinations that I wanted to visit on my Spring Break. The property is rural and quiet. "
Serenity Cottage: Central to state parks, historic towns, MD & VA beaches
Small cottage for those little getaways
Situated in a residential area, this cabin offers a peaceful retreat surrounded by mature trees and a grassy yard with ocean views.

Small cottage for those little getaways

10.0 out of 10, Exceptional, (110)
"Quiet, romantic getaway in a pretty setting. The cottage is lovely with nice furnishings. I loved the screened in porch."
Small cottage for those little getaways
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
A simple, single-story building with two entrance doors and a grassy surroundings.

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

9.6 out of 10, Exceptional, (25)
"Vacation very enjoyable and peaceful"
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
A small, single-story cabin with a gabled roof, featuring a front door and a porch area.

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

10.0 out of 10, Exceptional, (13)
"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
Enjoy a home away from home with a front porch and a deck area.

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
Staircase leads to a cozy porch with a brown door and a wooden deck.

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

10.0 out of 10, Exceptional, (17)
"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"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Waterfront Maryland Retreat w/ Dock & Bay View!
Relax by the beach with a fire pit and comfortable seating.

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (9)
"Beautiful sunset views and well accommodating house. "
Waterfront Maryland Retreat w/ Dock & Bay View!
COTTAGE BLUEFISH on Chincoteague Island! A cozy island getaway -NEW REMODEL
Welcome to this charming single-story home with a cozy porch and lush greenery.

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

10.0 out of 10, Exceptional, (10)
"Perfect space to return to at the end of an active day. Plenty of resting and relaxing."
COTTAGE BLUEFISH on Chincoteague Island! A cozy island getaway -NEW REMODEL
6 Mi to Salisbury: Forest-view Sanctuary!
Enjoy dining or relaxing on the deck surrounded by a wooded area.

6 Mi to Salisbury: Forest-view Sanctuary!

3.0 star property
$213 nightly
The price is $238
Aug 21 - Aug 22
Total includes taxes and fees
6 Mi to Salisbury: Forest-view Sanctuary!
Chincoteague House w/ Enclosed Porch + Deck
Relax in this serene outdoor patio with a round table and comfortable seating for two.

Chincoteague House w/ Enclosed Porch + Deck

3.0 star property
Chincoteague House w/ Enclosed Porch + Deck
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Relax on the beach with lounge chairs and a shaded gazebo overlooking the calm waters.

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

9.6 out of 10, Exceptional, (46)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
NEW PET FRIENDLY LISTING ALERT!!
Enjoy a tranquil home with a well-maintained lawn, brick chimney, and garden, perfect for outdoor activities.

NEW PET FRIENDLY LISTING ALERT!!

9.4 out of 10, Exceptional, (12)
"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!!
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Cozy single-story home with a gabled roof and a welcoming front porch.

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

9.0 out of 10, Wonderful, (2)
"very clean and neat, quiet. just what i needed"
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Pet-Friendly Smith Island Cottage w/ Golf Cart!
A small, single-story building with a gabled roof, surrounded by a white picket fence and a paved walkway.

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!
Beautiful, Waterfront, Luxury
Relax on the patio surrounded by lush greenery and a serene water view.

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
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 Princess Anne Hotel Reviews

Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort

10/10 Excellent
"Our family vacation was the week of the annual pony swim. Despite the fact that the hotel was extremely busy, the 100th anniversary swim, the staff was more than accommodating. They were extremely helpful and kind and polite. They went above and beyond. We even got a phone call about a half hour after check-in to make sure we settled in ok and if we needed anything! It's these little things that go a long way! Breakfast was excellent each morning with a variety of foods. The rooms were clean and in excellent shape. It was more than spacious for the 6 of us! Both indoor and outdoor pools were great! Kids went fishing off the pier, although they didn't catch anything. Hotel within walking distance to little park as well as some wonderful shops on the main street. "
Bernice 6-night trip
Posted 1 day ago
Comfort Suites Chincoteague Island Bayfront Resort