A sunset over a lake with a dock and a small settlement.

Princess Anne Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Princess Anne holiday rentals

Exterior

1. Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
Newark
10.0 out of 10, Exceptional, (13 reviews)
"Really comfortable and relaxing place to stay. Great service from host. "
United States
Roni V.
The price is HK$1,557
HK$4,063 total
includes taxes & fees
31 Aug - 1 Sept
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
Interior

2. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (139 reviews)
"Awesome two night stay! Highly recommend! "
United States
Dorothy D.
The price is HK$2,642
HK$4,389 total
includes taxes & fees
16 Aug - 17 Aug
Pet-friendly creekside cottage w/ backyard
Interior

3. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
The price is HK$1,898
HK$3,909 total
includes taxes & fees
20 Aug - 21 Aug
2 Mi to Downtown: Tranquil Abode in Chincoteague!
Interior

4. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
Up the Neck
10.0 out of 10, Exceptional, (6 reviews)
"My experience was beyond perfect! The house and yard was perfect. The house was so cozy and had everything we needed. I loved the little game room."
United States
Katlyn
The price is HK$1,506
HK$4,007 total
includes taxes & fees
20 Aug - 21 Aug
2 Mi to Downtown: Tranquil Abode in Chincoteague!
Smart TV, books

5. Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
10.0 out of 10, Exceptional, (5 reviews)
The price is HK$1,725
HK$2,951 total
includes taxes & fees
31 Aug - 1 Sept
Cozy 2-bedroom house in Chincoteague
TV, DVD player

6. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (30 reviews)
"Had a great stay! Place was very clean and host was great a communication."
United States
Jen G.
Assateageue Inn 104 by Seaside Vacations & Sales
Exterior

7. Bella's Beach Retreat by Seaside Vacations & Sales

Bella's Beach Retreat by Seaside Vacations & Sales
Chincoteague Island
8.0 out of 10, Very good, (9 reviews)
"Off season rates are really reasonable- place is as described- good location- good views- would stay again."
United States
Cindy H.
The price is HK$1,120
HK$1,924 total
includes taxes & fees
12 Aug - 13 Aug
Bella's Beach Retreat by Seaside Vacations & Sales
Beach nearby

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

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Birch Town
9.6 out of 10, Exceptional, (47 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is HK$1,875
HK$4,448 total
includes taxes & fees
13 Aug - 14 Aug
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Beach nearby, sun-loungers

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

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Downtown Chincoteague
10.0 out of 10, Exceptional, (78 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is HK$1,725
HK$3,320 total
includes taxes & fees
16 Aug - 17 Aug
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
1 bedroom, premium bedding, laptop workspace, soundproofing

10. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (604 reviews)
"Beautiful family friendly place. Great pool. Great location."
United States
KRYSTLE
The price is HK$2,408
HK$2,704 total
includes taxes & fees
16 Aug - 17 Aug
Key West Cottages
Smart TV, books

11. Misty Mare Townhouse - Gorgeous home on Chincoteague Island

Misty Mare Townhouse - Gorgeous home on Chincoteague Island
Snotty Ridge
10.0 out of 10, Exceptional, (16 reviews)
"This is an amazing place to stay! "
United States
Brenda D.
The price is HK$1,255
HK$2,871 total
includes taxes & fees
18 Aug - 19 Aug
Misty Mare Townhouse - Gorgeous home on Chincoteague Island
Outdoor dining

12. Sunset Bay Villas at Chincoteague Island Virginia - direct water front

Sunset Bay Villas at Chincoteague Island Virginia - direct water front
Downtown Chincoteague
9.8 out of 10, Exceptional, (128 reviews)
"Great place with excellent views! Check in was effortless and the condo was one of the cleanest I’ve seen. This was our first time visiting Chincoteague and we will definitely be back!"
United States
Danielle B.
The price is HK$5,490
HK$8,605 total
includes taxes & fees
15 Aug - 16 Aug
Sunset Bay Villas at Chincoteague Island Virginia - direct water front
Exterior

13. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (293 reviews)
"Excellent place to stay would definitely come again. Checking in was seem less and the staff very helpful"
United States
Jared
The price is HK$2,322
HK$3,048 total
includes taxes & fees
5 Aug - 6 Aug
Blufin Bungalows & Marina
TV

14. Assateague Inn 106 by Seaside Vacations & Sales

Assateague Inn 106 by Seaside Vacations & Sales
Chincoteague Island
9.8 out of 10, Exceptional, (8 reviews)
"Cute rooms in close proximity to several restaurants. "
United States
Sandy G.
Assateague Inn 106 by Seaside Vacations & Sales
Exterior

15. Assateague Inn 107 by Seaside Vacations & Sales

Assateague Inn 107 by Seaside Vacations & Sales
Chincoteague Island
8.8 out of 10, Excellent, (6 reviews)
"We had a wonderful time! The location was convenient to restaurants and shopping but still nice and quiet. Communication was easy and questions were answered quickly. "
United States
Katelyn W.
The price is HK$1,317
HK$2,169 total
includes taxes & fees
23 Aug - 24 Aug
Assateague Inn 107 by Seaside Vacations & Sales
Exterior

16. Assateague Inn 206 by Seaside Vacations & Sales

Assateague Inn 206 by Seaside Vacations & Sales
Chincoteague
2.0 out of 10, (1 review)
"The entire parking lot was completely flooded. There was no cover on the stairs leading to the second floor so the wood was extremely slick. We never checked into this property because we could not unload at this property. This is by far the worst experience I've ever had. In contacting the property manager we were told there was absolutely nothing that could be done. And we were just out the money."
United States
sam z.
Assateague Inn 206 by Seaside Vacations & Sales
Exterior

17. Assateague Inn 103 by Seaside Vacations & Sales

Assateague Inn 103 by Seaside Vacations & Sales
Chincoteague Island
8.0 out of 10, Very good, (6 reviews)
"The property and room were clean and neat. The facility and rooms are older, but all was functional and clean. Very communicative and easy and clear check in and out process! "
United States
Ellen K.
The price is HK$1,102
HK$1,895 total
includes taxes & fees
10 Aug - 11 Aug
Assateague Inn 103 by Seaside Vacations & Sales
Interior

18. Deck & EV Charger: Coastal Retreat 1 Mi to Marina

Deck & EV Charger: Coastal Retreat 1 Mi to Marina
3.0 star property
Captain's Cove
The price is HK$3,576
HK$6,590 total
includes taxes & fees
7 Aug - 8 Aug
Deck & EV Charger: Coastal Retreat 1 Mi to Marina
Pool

19. Deck & EV Charger: Coastal Retreat 1 Mi to Marina

Deck & EV Charger: Coastal Retreat 1 Mi to Marina
Captain's Cove
The price is HK$3,004
HK$6,739 total
includes taxes & fees
12 Aug - 13 Aug
Deck & EV Charger: Coastal Retreat 1 Mi to Marina
Smart TV, offices

20. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (68 reviews)
"We absolutely love staying here! "
United States
Maggie G.
The price is HK$2,347
HK$5,605 total
includes taxes & fees
4 Aug - 5 Aug
Bayfront Modern Retreat • Dock, Kayaks, Views
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
"Very clean room ( room 221 ), balcony, hallway, elevator, etc. Everything clean which I'm so thankful for because I have environmental allergies. Good breakfast, breakfast is until 11 am. My family enjoyed, and liked it as well. Helpful sttaffing, they answered all our questions."
Marjorie 1-night trip
Posted 4 hours ago
Comfort Suites Chincoteague Island Bayfront Resort

Find out more about Princess Anne

Search for holiday rentals in Princess Anne on Expedia! You can easily find your home rentals, villas, holiday apartments in Princess Anne using one of the methods below:

  • View our selection of featured holiday rentals in Princess Anne
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  • Enter your travel dates to view the best deals on holiday rentals in Princess Anne while they last

Look no further and take a look at our great range of rental properties in Princess Anne!

Frequently asked questions

Can I find a holiday rental in Princess Anne?

Yes, there are holiday rentals in Princess Anne close to Ella Fitzgerald Performing Arts Center, 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.

How many holiday rentals are there in Princess Anne?

Expedia has 3 holiday rentals for your stay in Princess Anne.

What can I see and do in Princess Anne?

Monie Island and Manokin Park are a couple of lovely local spots to get outside and enjoy nature. Somerset County Library and Hytche athletic Center 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.