Holiday Homes in Princess Anne

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Princess Anne

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
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 AU$1,065
includes taxes & fees
11 Sept - 12 Sept
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
Cottage near the Bay
Dining

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is AU$292
includes taxes & fees
17 Aug - 18 Aug
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

9.6 out of 10, Exceptional, (15)
"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."
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
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!
Seas the Moment - Bay, Channel, AND OCEAN VIEWS!
Terrace/patio

Seas the Moment - Bay, Channel, AND OCEAN VIEWS!

9.4 out of 10, Exceptional, (3)
"Will reserve this house many time is possible. Great location, new house and great comfort. Amazing place "
Seas the Moment - Bay, Channel, AND OCEAN VIEWS!
Deja Blue on Chincoteague Island
Dining

Deja Blue on Chincoteague Island

9.4 out of 10, Exceptional, (9)
"Great communications and great little get away"
Deja Blue on Chincoteague Island
Home on Smith Island in the Chesapeake Bay with golf cart, kayaks and SUP
Interior

Home on Smith Island in the Chesapeake Bay with golf cart, kayaks and SUP

9.8 out of 10, Exceptional, (11)
"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."
The price is AU$536
includes taxes & fees
15 Aug - 16 Aug
Home on Smith Island in the Chesapeake Bay with golf cart, kayaks and SUP
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, (32)
"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
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Exterior

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

9.6 out of 10, Exceptional, (42)
"We enjoyed our stay at Waterside. Location was perfect and host was very responsive to questions. A great rental for a few friends and/or family."
The price is AU$683
includes taxes & fees
2 Sept - 3 Sept
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
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 AU$460
includes taxes & fees
14 Sept - 15 Sept
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
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 AU$801
includes taxes & fees
3 Sept - 4 Sept
Stunning waterfront panoramic view getaway house
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)
"Nice property with lots of space."
The Brass Crab - Check in/out any day!
Sunset Breeze - Waterfront!
Smart TV

Sunset Breeze - Waterfront!

9.8 out of 10, Exceptional, (8)
"Comfortable and charming with great bay view "
Sunset Breeze - Waterfront!
Quaint Cottages Near Everything on Beach Road
Exterior

Quaint Cottages Near Everything on Beach Road

9.4 out of 10, Exceptional, (36)
"Location, location, location"
Quaint Cottages Near Everything on Beach Road
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 AU$696
includes taxes & fees
24 Aug - 25 Aug
The purple door at the bay.
Beautiful Bayfront with Sanctuary Private Beach
Property grounds

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (20)
"The property is beautiful and it was so nice to be so close to the water. Sunset view and fire pit out back were fun bonuses. Everything went smoothly and as expected. We enjoyed our stay, thank you!"
Beautiful Bayfront with Sanctuary Private Beach
Anchor's Away - Waterfront, Pet Friendly, Pools!
Property grounds

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

Anchor's Away - Waterfront, Pet Friendly, Pools!
Tranquil Tides Retreat - Waterfront on Chincoteague Island!
Outdoor dining

Tranquil Tides Retreat - Waterfront on Chincoteague Island!

2.0 star property
9.4 out of 10, Exceptional, (3)
"My stay was very nice. The place was clean and had great views!!! "
Tranquil Tides Retreat - Waterfront on Chincoteague Island!
Mermaid & Mare, Downtown Retreat. Hot Tub, Firepit, fenced yard & Pet Friendly!
Terrace/patio

Mermaid & Mare, Downtown Retreat. Hot Tub, Firepit, fenced yard & Pet Friendly!

10.0 out of 10, Exceptional, (2)
"The place is lovely, just as described in the listing. The host was very responsive and we had a wonderful time in Chincoteague. "
Mermaid & Mare, Downtown Retreat. Hot Tub, Firepit, fenced yard & 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

Waterside Inn

Waterside Inn

10/10 Excellent
"Spotlessly clean, beautiful setting, nice pool area by the water.Reasonable rates for in-season. They kindly allowed us to check in an hour early. Free breakfast. We only stayed one night, but would definitely book here again!"
Catherine 1-night trip
Posted 20 hours ago
Waterside Inn