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Compare 516 Vacation Homes in Princess Anne with updated reviews, rates, and availability.

Blufin Bungalows & Marina
Reception
Blufin Bungalows & Marina
3.0 star property
9.4 out of 10, Exceptional, (80)
"We enjoyed the floating bungalow. Nice to have somewhere different to try."
Blufin Bungalows & Marina
Historic Family Vacation Home with Golf Cart
Exterior
Historic Family Vacation Home with Golf Cart
9.6 out of 10, Exceptional, (4)
"Everything exceeded our expectations and the check out process was very simple"
Historic Family Vacation Home with Golf Cart
Quaint Cottages Near Everything on Beach Road
Living area
Quaint Cottages Near Everything on Beach Road
9.6 out of 10, Exceptional, (35)
"We booked this at the very last minute so we could clean out our father’s home (he passed the week before). It was perfect for our needs. One caution…the grass has tiny little burrs that stick to socks and flip flops. Nothing to do about them but if you have a dog, check their paws. We were even able to add an additional night easily when the clean out took longer than we expected. I would recommend!"
Quaint Cottages Near Everything on Beach Road
The Brass Crab - Check in/out any day!
Welcome to your vacation
The Brass Crab - Check in/out any day!
10.0 out of 10, Exceptional, (143)
"It is my birthday weekend and to celebrate I wanted to rent a beach house"
The Brass Crab - Check in/out any day!
This breathtaking New Home is located close to everywhere you want to be.
Share stories of the day's adventures around the toasty fire.
This breathtaking New Home is located close to everywhere you want to be.
10.0 out of 10, Exceptional, (48)
"4 minute walk to my family cottage on Main Street. Very convenient."
This breathtaking New Home is located close to everywhere you want to be.
Cottage near the Bay
Dining
Cottage near the Bay
8.6 out of 10, Excellent, (27)
"Attended a family wedding in the area. Perfect distance "
The price is SAR 338
SAR 749 total
includes taxes & fees
12 Nov - 13 Nov
Cottage near the Bay
Ariel`s Grotto is a gorgeous 3 Bedroom/2.5 Bath Vacation Rentals on incredible C
Discover the treasure that is Ariel`s Grotto on Chincoteague Island.
Ariel`s Grotto is a gorgeous 3 Bedroom/2.5 Bath Vacation Rentals on incredible C
9.8 out of 10, Exceptional, (81)
"Beautiful Fun House"
Ariel`s Grotto is a gorgeous 3 Bedroom/2.5 Bath Vacation Rentals on incredible C
Vanity Fair - 4BR/2.5B HUGE DECKS,LINENS AND TOWELS
Vanity Fair - 4BR/2.5B HUGE DECKS,LINENS AND TOWELS
9.8 out of 10, Exceptional, (16)
"Plenty of space for 6 people to stay without tripping over each other. Room for eating meals together inside or on the porch. Close to shops, restaurants, and ice cream for biking."
Vanity Fair - 4BR/2.5B HUGE DECKS,LINENS AND TOWELS
Sea Pines -2BR CLOSE TO SHOPPING,SCREENED PORCH, Linens and Towels Provided
Sea Pines -2BR CLOSE TO SHOPPING,SCREENED PORCH, Linens and Towels Provided
9.2 out of 10, Wonderful, (14)
"We thoroughly enjoyed this house. Solid construction weathered the storm that blew through one day. Sparkling clean throughout, carpet was new, sofa was super comfy for sitting or lounging on. There was a stool in the closet for reaching higher cabinets so I was glad to see previous complaints in reviews had been addressed. It was just my husband and myself but this would be a good choice for a small family too. We enjoyed the quiet and the privacy of the screened porch. There were no basic...
Sea Pines -2BR CLOSE TO SHOPPING,SCREENED PORCH, Linens and Towels Provided
Cozy Nest - Waterview, Pet Friendly, Screened Porch
Cozy Nest - Waterview, Pet Friendly, Screened Porch
10.0 out of 10, Exceptional, (3)
"We loved the cozyness of this location and the view from the bedroom upstairs was just breathtaking. No better place to open the windows and enjoy theocean breeze and the "
Cozy Nest - Waterview, Pet Friendly, Screened Porch
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
Deal Island Historic District Vacation Rental | 4BR | 2BA | 2 Steps Required
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
2.0 star property
10.0 out of 10, Exceptional, (2)
"Perfect home for family gathering. Kitchen well equipped with all appliances and condiments. Bedrooms clean, with comfortable beds and linens. Beautiful views from the screened porch in backyard of Tanger Sound and colorful sunsets in hues of red, orange and yellow. Quick communication with owner. Would definitely stay again!"
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
Oyster Bay Hideaway on Chincoteague Island!
Welcome to Oyster Bay Hideaway in the heart of Chincoteague Island.
Oyster Bay Hideaway on Chincoteague Island!
10.0 out of 10, Exceptional, (8)
"It was great!"
Oyster Bay Hideaway on Chincoteague Island!
To the Lighthouse (formerly Epiphany) is a breathtaking 3 Bedroom/3 Full Bath Va
Welcome to To the Lighthouse - A stunning Chincoteague Home with amazing Updates
To the Lighthouse (formerly Epiphany) is a breathtaking 3 Bedroom/3 Full Bath Va
9.6 out of 10, Exceptional, (61)
"Beautiful and relaxing location. The house was clean and the kitchen well stocked. "
To the Lighthouse (formerly Epiphany) is a breathtaking 3 Bedroom/3 Full Bath Va
Beautiful Bayfront with Sanctuary Private Beach
Beach
Beautiful Bayfront with Sanctuary Private Beach
9.0 out of 10, Wonderful, (17)
"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
Lily Pad on Chincoteague Island - Lighthouse Views and Pet Friendly!
Lily Pad has lovely Views of the Assateague Lighthouse!
Lily Pad on Chincoteague Island - Lighthouse Views and Pet Friendly!
9.4 out of 10, Exceptional, (43)
"Great place for the price. 10/10 stay. Only small complaint is that the patio furniture, fridge, and radiators are older and have visible rust damage (but still work fine) and the floors were dirty when we arrived"
Lily Pad on Chincoteague Island - Lighthouse Views and Pet Friendly!
Miss Agnes - Water Front 3BR home PET FRIENDLY, NO LINENS PROVIDED
Miss Agnes - Water Front 3BR home PET FRIENDLY, NO LINENS PROVIDED
9.4 out of 10, Exceptional, (53)
"A bit outdated and neglected. Stairs to bedrooms are very steep."
Miss Agnes - Water Front 3BR home PET FRIENDLY, NO LINENS PROVIDED
Breathe the Bay - Waterfront w/ Dock, Pool & Golf!
Exterior
Breathe the Bay - Waterfront w/ Dock, Pool & Golf!
9.4 out of 10, Exceptional, (6)
"Great place , I bit isolated but doable. Everyone very friendly, amenities setup is a bit of a pain in the ass . "
Breathe the Bay - Waterfront w/ Dock, Pool & Golf!
Cypress Cottage -Waterview-TOWN LINENS AND TOWELS /Beach Supplies Provided
Cypress Cottage -Waterview-TOWN LINENS AND TOWELS /Beach Supplies Provided
10.0 out of 10, Exceptional, (13)
"This place was everything that they say about it and some additional things as well. Very well equipped with beachwear and kitchen amenities. Well, shaded by the trees so that we ate most of our meals outside. And the outdoor shower is fantastic after the beach. I highly recommend this place. It was wonderful!"
Cypress Cottage -Waterview-TOWN LINENS AND TOWELS /Beach Supplies Provided
Vast Views - Pet friendly; Shared pool!
Vast Views - Pet friendly; Shared pool!
8.4 out of 10, Very Good, (19)
"The property's location and lighthouse view made it very appealing. I think the house has plenty of room with a very good layout. I do think it could use some updating and TLC."
Vast Views - Pet friendly; Shared pool!
Island Retreat - Lovely Marsh Views and Pet Friendly!
Welcome to Island Retreat - the only thing missing here is YOU.....
Island Retreat - Lovely Marsh Views and Pet Friendly!
9.0 out of 10, Wonderful, (7)
"This is a gorgeous location, right on the marsh, in a quiet neighborhood but just blocks from restaurants & shops. We were perfectly comfortable & enjoyed watching the geese & herons on the water. We’ll be back!"
Island Retreat - Lovely Marsh Views and 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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Other property types in Princess Anne

Key West Cottages
Exterior
Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (291)
"The Key West Cottages were beyond exceptional! The property is perfect in so many ways - the location is convenient and picturesque, the property is immaculate, well maintained and everything is like “new” condition. Units are easy to access and walkways are safe and clear. The only elevation is in the four steps to your front door! Plenty of parking, walking convenient to everything in town and restaurants, The pool and the beach area are very lovely, intimate and easily accessed. The...
The price is SAR 423
SAR 475 total
includes taxes & fees
24 Nov - 25 Nov
Key West Cottages
Blufin Bungalows & Marina
Reception
Blufin Bungalows & Marina
3.0 star property
9.4 out of 10, Exceptional, (80)
"We enjoyed the floating bungalow. Nice to have somewhere different to try."
Blufin Bungalows & Marina
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
Exterior
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
9.8 out of 10, Exceptional, (275)
"Clean and quiet. Efficient use of space"
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
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.