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

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Princess Anne cottages

A single-story house with a front porch, a staircase leading to the entrance, and a small deck.

1. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"
United States
Harold B.
$243 nightly
The price is $257
Oct 15 - Oct 16
Total with taxes and fees
Deal Island Bay Cottage
A waterfront house with a balcony, dock, and a view of the water.

2. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (658 reviews)
"First time here and we absolutely loved it."
United States
Melissa
$215 nightly
The price is $242
Oct 14 - Oct 15
Total with taxes and fees
Key West Cottages
Welcome to Creekside Retreat!

3. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (140 reviews)
"The house was very clean and tidy when we arrived. We appreciated having our linens supplied, the very clear house manual with all instructions and clear communication on how to access the house. We also liked how the host checked in to see how we were doing and if we had any needs. This house was also pet friendly."
United States
Christine
$308 nightly
The price is $335
Oct 15 - Oct 16
Total with taxes and fees
Pet-friendly creekside cottage w/ backyard
Exterior

4. Creekside Cottage with Sunroom and Fire Pit - with Plenty of Outdoor Space Near Assateague Island in Chincoteague, VA

Creekside Cottage with Sunroom and Fire Pit - with Plenty of Outdoor Space Near Assateague Island in Chincoteague, VA
Up the Neck
$465 nightly
The price is $522
Oct 15 - Oct 16
Total with taxes and fees
Creekside Cottage with Sunroom and Fire Pit - with Plenty of Outdoor Space Near Assateague Island in Chincoteague, VA
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

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

10/10 Excellent
"Bed was comfortable, everything was clean, staff are very helpful and nice."
Rachel 1-night trip
Posted less than an hour ago
Best Western Plus Pocomoke City

Find out more about Princess Anne

Princess Anne Cottages information

Number of reviews
860
Accommodation
95 Cottages
Lowest Price
$242
Highest Price
$522

Frequently asked questions

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What is there to do in Princess Anne near my cottage?
The ideal travel accessory is a well-thought-out travel plan. Hytche athletic Center is a wonderful place to kick off your exploration of Princess Anne.

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