Princess Anne Holiday Rentals

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Holiday Rentals in Princess Anne

Blufin Bungalows & Marina
Exterior

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (166)
"excellent place to stay on the water"
Blufin Bungalows & Marina
Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (432)
"Great place to stay!"
Key West Cottages
Strawberry Crossroads
Exterior

Strawberry Crossroads

2.0 star property
8.8 out of 10, Excellent, (6)
"My family really enjoyed the stay, its close enough drive to ocean city while being out of the way. Even after having a double booking issue the property owner made it work for us all. The kids were begging us to stay longer it was so peaceful!"
Strawberry Crossroads
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 HK$820
HK$3,141 total
includes taxes & fees
3 Sept - 4 Sept
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Pool

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

9.6 out of 10, Exceptional, (13)
"Great location, very clean and amazing staff. I highly recommend staying here."
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
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 It was good enough for us to relax and cook but a slight bit expensive for its outdated condition though."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 HK$1,230
HK$3,520 total
includes taxes & fees
24 Aug - 25 Aug
The purple door at the bay.
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Beach

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

9.6 out of 10, Exceptional, (48)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Cabin at Holdens Creek on Eastern Shore of VA
Interior

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (172)
"Beautiful cabin situated at the back of a farm, very peaceful. Very spacious and inviting. Only a half hour to Chincoteague and an hour to Ocean City. Nice porch with a swing and 2 chairs to sit out in the morning with a cup of coffee (coffee maker provided). We loved having a pool table for our evening entertainment. Only thing we didn't like was the very tiny kitchen, absolutely no counter space at all :( "
Cabin at Holdens Creek on Eastern Shore of VA
NEW PET FRIENDLY LISTING ALERT!!
Smart TV, fireplace

NEW PET FRIENDLY LISTING ALERT!!

9.6 out of 10, Exceptional, (14)
"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!!
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 HK$914
HK$2,264 total
includes taxes & fees
4 Sept - 5 Sept
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Waterfront on Marsh Island!
Interior

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (32)
"We stayed in the "Lovers Lane" unit which is on the lower level of this small condo unit. It had access to a secure laundry room, private deck with picnic table, BBQ grill and awesome lighting for night crabbing or fishing right from your private dock! Couldn't ask for more. The unit was very clean. This location has great access to Chincoteague with easy egress and ingress from the Island. If your looking for a quiet stay away from the commercial hustle, this is the place, though the room...
Waterfront on Marsh Island!
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
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!
The Hideaway Cottage
Beach nearby

The Hideaway Cottage

9.8 out of 10, Exceptional, (92)
"Just right for what we needed."
The Hideaway Cottage
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!
Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague

9.8 out of 10, Exceptional, (50)
"Great location and property for a peaceful and tranquil getaway."
Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague
5 minutes to Assateague National Seashore!
Flat-screen TV

5 minutes to Assateague National Seashore!

8.8 out of 10, Excellent, (16)
"There was enough space for 3 adults and to children. The bathroom in the hall has not been updated. The shower was crudy and no towel rack. The spicket for shower/bath in the 2nd bathroom was almost impossible to use. The rental was okay."
The price is HK$848
HK$1,542 total
includes taxes & fees
17 Sept - 18 Sept
5 minutes to Assateague National Seashore!
Cottage near the Bay
Dining

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is HK$633
HK$1,474 total
includes taxes & fees
31 Aug - 1 Sept
Cottage near the Bay
Only 5 min to Assateague National Seashore!
Terrace/patio

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (18)
"Nice place. "
The price is HK$848
HK$1,577 total
includes taxes & fees
9 Sept - 10 Sept
Only 5 min to Assateague National Seashore!
Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS
Exterior

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
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 1 day ago
Key West Cottages

Frequently asked questions

Can I find a holiday rental in Princess Anne?

Yes, there are holiday rentals close to the most popular sights in Princess Anne, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Princess Anne has a good selection of restaurants. Make sure you have time to check out the beaches and shopping during your trip.

What are some of the best holiday rentals that Princess Anne has to offer?

Blufin Bungalows & Marina: This holiday home rental outside of Princess Anne is on the beach, and equipped with free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

What can I see and do in Princess Anne?

Manokin Park and Wellington State Wildlife Management Area are a couple of lovely local spots to get outside and enjoy nature. Somerset County Library and Princess Anne Town Hall are other places to visit while you're in town.

What are holiday rentals like in Princess Anne?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Princess Anne. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips.