Holiday Homes in Princess Anne

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Princess Anne and around

Our top choices for Princess Anne holiday homes

Blufin Bungalows & Marina
Exterior

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (165)
"excellent place to stay on the water"
Blufin Bungalows & Marina
The purple door at the bay.
Terrace/patio

The purple door at the bay.

9.2 out of 10, Wonderful, (51)
"Property was slightly run down and had no driveway (just grass). It was in a great neighborhood with a beautiful view. We had to take the trash 15 minutes south when leaving (in the opposite direction of home for us). It was good enough for us to relax and cook but a slight bit expensive for its outdated condition though."
The price is €397
includes taxes & fees
24 Aug - 25 Aug
The purple door at the bay.
Cottage near the Bay
Dining

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is €164
includes taxes & fees
1 Sept - 2 Sept
Cottage near the Bay
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Terrace/patio

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

9.8 out of 10, Exceptional, (16)
"We stayed three nights and they were all delightful. The cabins are super clean, well equipped, comfortable beds, screened in front porch.- in other words anything you could wish! My only critique is that I don’t think the smoke alarm in the CO2 detectors were listed in the ad and they should be because they definitely are there!We will gladly come again someday."
The price is €405
includes taxes & fees
28 Aug - 29 Aug
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Quaint Cottages Near Everything on Beach Road
Exterior

Quaint Cottages Near Everything on Beach Road

9.4 out of 10, Exceptional, (39)
"Location, location, location"
Quaint Cottages Near Everything on Beach Road
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
Fridge, microwave, oven, stovetop

3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

10.0 out of 10, Exceptional, (2)
"Place was amazing. Super clean and host let us snacks and flowers, nice touch. Just wish zi would have asked if the pool access was inckuded. That is the only thing that could have made it any better. 10/10 recommend "
The price is €605
includes taxes & fees
24 Aug - 25 Aug
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Fridge, microwave, oven, stovetop

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

10.0 out of 10, Exceptional, (55)
"Thank you so much for letting us stay at your house. The location was perfect for walking to restaurants and shops. Did a day at the wildlife refuge and spent some time on the beach. Plan to come back and enjoy another stay. "
The price is €255
includes taxes & fees
4 Sept - 5 Sept
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
The Brass Crab - Check in/out any day!
Fridge, microwave, oven, stovetop

The Brass Crab - Check in/out any day!

10.0 out of 10, Exceptional, (151)
"The Brass Crab is the perfect family place to stay. Thank you for all the extras."
The Brass Crab - Check in/out any day!
Historic home on Smith Island w/ dock!
Beach

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (43)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!
No Problem (Formerly The Teague House) - Wonderful Waterfront!
Marina

No Problem (Formerly The Teague House) - Wonderful Waterfront!

9.6 out of 10, Exceptional, (8)
"Stayed at many places on the island over the years. This place was truly the best. Fully stocked and very clean."
No Problem (Formerly The Teague House) - Wonderful Waterfront!
Cattail Cottage -Allergy Friendly Home -In Town-LINENS & TOWELS PROVIDED
Terrace/patio

Cattail Cottage -Allergy Friendly Home -In Town-LINENS & TOWELS PROVIDED

9.6 out of 10, Exceptional, (33)
"This charming, coastal themed cottage was conveniently located to Assateague Island, Wallops Island, and Chincoteague! It was clean, gave abundant information on the area, and in a quiet location. My husband and I enjoyed our stay at our home away from home for a reasonable price!"
Cattail Cottage -Allergy Friendly Home -In Town-LINENS & TOWELS PROVIDED
Stunning waterfront panoramic view getaway house
Property grounds

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (53)
"The roundhouse was amazing on many levels, figuratively and literally. There are many creature, comforts throughout this sprawling home and the views were serene and relaxing, and the couches and beds were comfy! And the host was very helpful and accommodating. Highly recommend would definitely stay here again."
The price is €410
includes taxes & fees
1 Sept - 2 Sept
Stunning waterfront panoramic view getaway house
The Blue Crab - Your Dream Vacation awaits you!
Fridge, microwave, oven, stovetop

The Blue Crab - Your Dream Vacation awaits you!

2.0 star property
10.0 out of 10, Exceptional, (11)
"This was our second stay at this property. Plenty of room for us and our 2 small dogs.The house is perfectly maintained. Bathrooms are up to date and the kitchen is well equiped.We will be back in the Fall."
The Blue Crab - Your Dream Vacation awaits you!
Anchor's Away - Waterfront, Pet Friendly, Pools!
Property grounds

Anchor's Away - Waterfront, Pet Friendly, Pools!

Anchor's Away - Waterfront, Pet Friendly, Pools!
Sandy Moose - 3BRWaterfront home on lake, screened porch, LINENS AND TOWELS
Terrace/patio

Sandy Moose - 3BRWaterfront home on lake, screened porch, LINENS AND TOWELS

9.6 out of 10, Exceptional, (34)
"Great location"
Sandy Moose - 3BRWaterfront home on lake, screened porch, LINENS AND TOWELS
Welcome to Mabel Rose - Delightful 3 bedroom home on the Eastern Shore
Exterior

Welcome to Mabel Rose - Delightful 3 bedroom home on the Eastern Shore

10.0 out of 10, Exceptional, (95)
"Super cute place with a gracious host who lives next door. Enjoyed playing board games & reading on the screened-in porch while watching & listening to the birds. Would definitely stay here again. "
Welcome to Mabel Rose - Delightful 3 bedroom home on the Eastern Shore
Sweet cottage with outdoor shower
Fridge, microwave, oven, stovetop

Sweet cottage with outdoor shower

9.8 out of 10, Exceptional, (39)
"We enjoyed our week here. It was a perfect cottage for us. We enjoyed the screened in gazebo in the evenings and the convenient location."
The price is €424
includes taxes & fees
3 Sept - 4 Sept
Sweet cottage with outdoor shower
Walk to Main Street: Family-Friendly Crisfield Gem
Fridge, microwave, stovetop, dishwasher

Walk to Main Street: Family-Friendly Crisfield Gem

10.0 out of 10, Exceptional, (2)
"Beautiful property"
Walk to Main Street: Family-Friendly Crisfield Gem
Waterfront allergy-free home with 40-foot fishing dock, canoe, home theater
Fridge, microwave, oven, stovetop

Waterfront allergy-free home with 40-foot fishing dock, canoe, home theater

9.6 out of 10, Exceptional, (29)
"Loved it here! Will absolutely try and stay here next time I visit. Property was beautiful, area was perfect and location was spot on!"
Waterfront allergy-free home with 40-foot fishing dock, canoe, home theater
Painted Pony Cottage - Pet Friendly!
Terrace/patio

Painted Pony Cottage - Pet Friendly!

9.4 out of 10, Exceptional, (8)
"Nice place. Very comfortable and a good location close to town. We really enjoyed ourselves."
Painted Pony Cottage - Pet Friendly!
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

Key West Cottages

Key West Cottages

10/10 Excellent
"We've been visiting Chincoteague every summer for the past 10 years and this is the first time we've stayed at Key West Cottages and we were not disappointed. We appreciated the cleanliness of the cottage, having our own kitchen, and the private "beach" overlooking the bay. Despite being at full capacity with guests at the location it was quiet and we never felt like it was crowded or loud. Communication was great and the staff was very friendly. We'll be back!"
Jennifer 1-night trip
Posted 23 hours ago
Key West Cottages