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

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Our top choices for Princess Anne holiday homes

A sandy beach with footprints, a pier in the distance, and a clear sky.

A living room with a gray sectional sofa, wooden flooring, a hallway leading to a door, and a shelf with decorative items.

A hallway with a framed artwork of a bird, a wooden entertainment unit with a TV, and a dining area with a bar stool.

A dining area with a wooden table and benches, a small kitchen counter with decorative items, and a view through a window with curtains.

1. Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.

Deal Island Historic District

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Helpful host, clean house, peaceful location! "

Jennifer P.

The price is €218

€218

includes taxes & fees

1 Oct - 2 Oct

Tangier Escape, great place get away from it all on Deal Island, MD.

A single-story house with a front porch, a door, and a mailbox.

A modern living room with a grey sofa, a wooden coffee table, and a patterned rug.

A modern living room with a wooden coffee table, a black console table, and a large flat-screen TV mounted on the wall.

A house with a covered porch, outdoor seating, and a stone foundation.

2. Salisbury Hideaway

Salisbury Hideaway

Salisbury

10.0 out of 10, Exceptional, (23 reviews)

10/10

Exceptional

(23 reviews)

"Perfect for our weekend away watching college softball!!!"

Michelle S.

The price is €280

€280

includes taxes & fees

27 Sept - 28 Sept

Salisbury Hideaway

A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

A hallway with framed pictures on the wall, a light fixture on the ceiling, and a door leading to a bathroom.

A hallway with a framed plant, a bed with a patterned bedspread, and a decorative wall piece.

A modern kitchen with white cabinets, a dishwasher, a stove, and a dining area with a table and chairs.

3. Salisbury Cottage

Salisbury Cottage

Salisbury

10.0 out of 10, Exceptional, (40 reviews)

10/10

Exceptional

(40 reviews)

"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."

Matthew B.

The price is €312

€312

includes taxes & fees

19 Oct - 20 Oct

Salisbury Cottage

A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

A kitchen with wooden cabinets, a dining table with chairs, a refrigerator, a microwave, and a sink.

A living room with a brown leather couch, wooden walls, a television on a wooden cabinet, a door with blinds, and a framed picture on the wall.

A compact kitchen with wooden cabinets, a dining table with chairs, a refrigerator, a microwave, and a television.

4. Cottage near the Bay

Cottage near the Bay

Crisfield

8.6 out of 10, Excellent, (63 reviews)

8.6/10

Excellent

(63 reviews)

"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"

Pamela

The price is €167

€167

includes taxes & fees

3 Oct - 4 Oct

Cottage near the Bay

A kitchen with a farmhouse sign, a clock, and a refrigerator.

A two-story white house with a visible chimney and a small attached garage.

A residential driveway with two cars parked on the left, surrounded by trees and a grassy area.

A wooden staircase with a handrail, leading to a landing with wall-mounted artwork.

5. Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches

Pocomoke City

10.0 out of 10, Exceptional, (23 reviews)

10/10

Exceptional

(23 reviews)

"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "

Ryan B.

The price is €244

€244

includes taxes & fees

25 Sept - 26 Sept

Cozy Barn Loft: Country Views & Central to Beaches

A beach with a palm tree, blue chairs, and a small table.

A beachside deck with two blue Adirondack chairs, a green table, and a 'STAY OFF ROCKS' sign.

A coastal house with a wooden deck, large windows, and a view of the water.

6. Blufin Bungalows & Marina

Blufin Bungalows & Marina

3.0 star property

Down the Marsh

9.6 out of 10, Exceptional, (330 reviews)

9.6/10

Exceptional

(330 reviews)

"Superior views of the bay, very dog friendly"

Angela

The price is €199

€199

includes taxes & fees

13 Oct - 14 Oct

Blufin Bungalows & Marina

A room with a glass-top coffee table, a white dresser with gold handles, a white door, and a patterned rug.

A modern kitchen with wooden cabinets, a microwave, and a black backsplash.

A living room with a dining area, a TV, a white door, and a large mirror.

A dining area with a wooden table set for four, a television, a white door, and a living room with a sofa and a lamp.

7. Entire Private Home • Sleeps 6 • Prime Salisbury Location

Entire Private Home • Sleeps 6 • Prime Salisbury Location

Salisbury

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"The stay was great. "

Nathaniel N.

The price is €272

€272

includes taxes & fees

27 Sept - 28 Sept

Entire Private Home • Sleeps 6 • Prime Salisbury Location

A sandy beach with footprints and a person walking.

A two-story house with a balcony and a covered porch.

A kitchen with wooden cabinets, a welcome sign, a sink with a faucet, and a light bulb on the counter.

A living room with a sofa, chairs, a coffee table, and a TV.

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, (48 reviews)

9.6/10

Exceptional

(48 reviews)

"It was family & friends that needed a get away and we really Enjoy the area"

Lori D.

The price is €345

€345

includes taxes & fees

27 Sept - 28 Sept

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

A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

A coastal property with a large swimming pool, outdoor seating, and a view of the sea.

A waterfront property with a wooden deck, outdoor seating, and a multi-level building with balconies.

A modern living room with a sofa, a coffee table, and a dining area with a circular table.

9. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views

Captain's Cove

9.8 out of 10, Exceptional, (68 reviews)

9.8/10

Exceptional

(68 reviews)

"Overall nice stay!"

Becky S.

The price is €440

€440

includes taxes & fees

27 Sept - 28 Sept

Bayfront Modern Retreat • Dock, Kayaks, Views

A sunroom with wicker furniture, large windows, and a view of the water.

A two-story waterfront house with a covered deck, a dock, and a boat dock.

A spacious living area with a high ceiling, a staircase, and large windows.

A balcony with wicker chairs, a small table, and a vase with flowers.

10. The purple door at the bay.

The purple door at the bay.

Captain's Cove

9.4 out of 10, Exceptional, (67 reviews)

9.4/10

Exceptional

(67 reviews)

"Everything was just perfect. I will be back. This time for a long stay. My entire family loves the place. Thanks Kelly."

Francis

The price is €400

€400

includes taxes & fees

25 Sept - 26 Sept

The purple door at the bay.

A living room with a ceiling fan, a sofa, a coffee table, and a TV.

A turquoise and white building with the sign "Sir Whelk & Co." and a large bird sculpture on the roof.

A kitchen with a dining area, featuring a fish wall art, a clock, and a 'welcome' sign.

11. 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, (81 reviews)

10/10

Exceptional

(81 reviews)

"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."

Charles G.

The price is €255

€255

includes taxes & fees

30 Sept - 1 Oct

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

A cozy living room with a dining area, featuring a ceiling fan, a sofa, a coffee table, and a bookshelf.

A wooden deck with two chairs and a table.

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a sink. There are two stools and a small wooden table with placemats.

A room with a door, a white table with a blue and white sign, a black and white rug, and a small shelf with items.

12. Misty Mare Townhouse - Gorgeous home on Chincoteague Island

Misty Mare Townhouse - Gorgeous home on Chincoteague Island

Snotty Ridge

9.8 out of 10, Exceptional, (19 reviews)

9.8/10

Exceptional

(19 reviews)

"Great location, easy check in, very clean, well decorated"

sue g.

The price is €274

€274

includes taxes & fees

1 Oct - 2 Oct

Misty Mare Townhouse - Gorgeous home on Chincoteague Island

A row of three-story townhouses with a front porch, a small garden, and a clear blue sky.

A modern kitchen with white cabinetry, a stainless steel stove, and a dining area with a wooden table and white chairs.

A neatly made bed with white linens and pillows, a round side table with a vase of flowers, and a classic chair.

A modern kitchen with white cabinets, a stainless steel dishwasher, a microwave, and a tiled backsplash.

13. Central Location~Walk 2 Dining! Beach Pass & Gear!

Central Location~Walk 2 Dining! Beach Pass & Gear!

Deep Hole

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Excellent space with everything needed!"

Tianna B.

The price is €261

€261

includes taxes & fees

28 Sept - 29 Sept

Central Location~Walk 2 Dining! Beach Pass & Gear!

A cozy living room with a sofa, a coffee table, and a TV mounted on the wall.

A kitchen with wooden cabinets, a stainless steel stove, and a washing machine.

A room with a bed, a TV mounted on the wall, a dresser, and an air conditioning unit.

A room with a wooden ceiling, a mounted TV, a door with a window, and a black mat on the floor.

14. Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague

Deep Hole

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"The host was very responsive and brought toys over for our children to help occupy them while we were there. The host is also connected to the Daisey's Island Cruises and gave us a discounted price to take in the cruise while we were on the island. That was very enjoyable and helped us learn more about the island and the annual pony round-up. It suited our family of 5 well."

Cleason H.

The price is €268

€268

includes taxes & fees

30 Sept - 1 Oct

Cozy 2-bedroom house in Chincoteague

A marina at sunset with boats docked and buildings in the background.

A compact, modern bathroom with a sink, mirror, and two stacked washing machines.

A two-story house with a porch, a driveway, and a golf cart parked in front.

A two-story house with a front porch, white siding, and red shutters.

15. Come out and enjoy Autumn at the HH Ranch on Smith Island.

Come out and enjoy Autumn at the HH Ranch on Smith Island.

Smith Island

9.8 out of 10, Exceptional, (16 reviews)

9.8/10

Exceptional

(16 reviews)

"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"

Samantha J.

The price is €292

€292

includes taxes & fees

16 Oct - 17 Oct

Come out and enjoy Autumn at the HH Ranch on Smith Island.

A house surrounded by dense trees and a wooden dock extending into a body of water.

A bright yellow room with a spiral staircase, a ceiling fan, and a TV displaying a nature scene.

A wooden dock extending into a calm body of water, surrounded by dense trees and a house with a white fence.

A wooden dock extending over a calm body of water, surrounded by trees and a clear sky.

16. 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, (20 reviews)

10/10

Exceptional

(20 reviews)

"This place was perfect. Beds were comfy, it had everything i needed in the kitchen, secluded enough to feel like you were alone with nature but close enough to drive to tourist attractions. Literally everything we we looking for. Added bonus was napping in the screened in porch."

Jackie P.

The price is €415

€415

includes taxes & fees

5 Oct - 6 Oct

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

A house with a large lawn and a dock extending into a calm lake.

A large, single-story house with a central chimney, surrounded by a calm lake, reflecting the structure.

A snow-covered pier extending into a frozen body of water with a clear sky in the background.

An aerial view of a coastal landscape with a river meandering through a marshy area, surrounded by sparse vegetation and a distant shoreline.

17. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Fishing Creek

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."

Thomas S.

The price is €297

€297

includes taxes & fees

28 Sept - 29 Sept

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

A covered porch with a red swing chair, white chairs, and a view of the street.

A kitchen with wooden cabinets, a microwave, and a refrigerator.

A covered porch with a swing seat, a chair with a patterned cushion, and a small table with a potted plant.

A two-story house with a porch, a sign indicating parking, and a well-maintained lawn.

18. The Neigh-Neigh - Location! Location! Location!

The Neigh-Neigh - Location! Location! Location!

Downtown Chincoteague

9.8 out of 10, Exceptional, (7 reviews)

9.8/10

Exceptional

(7 reviews)

"Very nice place to stay close to town. Charming screened porch, well appointed kitchen, plenty of space for us."

Veronika B.

The price is €431

€431

includes taxes & fees

25 Sept - 26 Sept

The Neigh-Neigh - Location! Location! Location!

A beachside view with a wooden deck, a chair, and a table.

A pool area with lounge chairs and a clear view of the ocean.

A beach scene with a palm tree, a sign, and a bird flying.

A modern kitchen with white cabinetry, a stainless steel refrigerator, and a beige countertop.

19. Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Down the Marsh

9.8 out of 10, Exceptional, (16 reviews)

9.8/10

Exceptional

(16 reviews)

"Nice pet friendly accommodation. "

Claudia w.

The price is €258

€258

includes taxes & fees

2 Oct - 3 Oct

Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

A bedroom with a bed, a chair, and a window with curtains.

A circular sign with the words "WELCOME ABOARD" and an eagle illustration.

20. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Fishing Creek

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "

Robin E.

The price is €268

€268

includes taxes & fees

28 Sept - 29 Sept

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

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

Blufin Bungalows & Marina

10/10 Excellent

"Loved it…what a fun experience!"

Wendy 3-night trip

Posted 12 hours ago

Blufin Bungalows & Marina

Waterside Inn

10/10 Excellent

"The room was clean and comfortable the staff was so nice and helpful the breakfast was good and enough we enjoyed our stay and look forward to going back again."

Dwain 2-night trip

Posted 16 hours ago

Waterside Inn

Comfort Suites Chincoteague Island Bayfront Resort

10/10 Excellent

"Staff was very helpful. The grounds were very clean. Breakfast was excellent. Room was nice and clean. Loved the view from balcony overlooking the bay. Would definitely recommend this place."

John 2-night trip

Posted 1 day ago

Comfort Suites Chincoteague Island Bayfront Resort

Key West Cottages

8/10 Good

"The facilities were beautiful and the staff was very helpful and friendly."

Mark 3-night trip

Posted 2 days ago

Key West Cottages

Best Western Salisbury Plaza

8/10 Good

"I would have preferred non plastic plates and flatware"

Sarah 1-night trip

Posted 2 days ago

Best Western Salisbury Plaza

Atlantic Shores Inn and Suites

10/10 Excellent

"Very nice"

stewart 1-night trip

Posted 4 days ago

Atlantic Shores Inn and Suites

The Reserve Inn

10/10 Excellent

"Excellent 5 ✨✨✨✨"

Alba 1-night trip

Posted 4 days ago

The Reserve Inn

Days Inn by Wyndham Salisbury

10/10 Excellent

"Every thing was very convenient for me"

Terry 2-night trip

Posted 7 days ago

Days Inn by Wyndham Salisbury

Wingate by Wyndham Salisbury MD Airport North

10/10 Excellent

"EVERYTHING was AMAZING ESPECIALLY THE OVERNIGHT STAFF for the 3 days I stayed. THE POOL WATER WAS NOT OKAY. TOP LAYER WAS COVERED IN A FILM ALONG WITH HAIR. My only complaint."

Owen 1-night trip

Posted 8 days ago

Wingate by Wyndham Salisbury MD Airport North

Find out more about Princess Anne

Princess Anne Holiday Homes information

Number of reviews	687
Accommodation	644 Holiday Homes
Lowest Price	€167
Highest Price	€440

Holiday Homes in Princess Anne

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Princess Anne holiday homes

1. Tangier Escape, great place get away from it all on Deal Island, MD.

2. Salisbury Hideaway

3. Salisbury Cottage

4. Cottage near the Bay

5. Cozy Barn Loft: Country Views & Central to Beaches

6. Blufin Bungalows & Marina

7. Entire Private Home • Sleeps 6 • Prime Salisbury Location

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

9. Bayfront Modern Retreat • Dock, Kayaks, Views

10. The purple door at the bay.

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

12. Misty Mare Townhouse - Gorgeous home on Chincoteague Island

13. Central Location~Walk 2 Dining! Beach Pass & Gear!

14. Cozy 2-bedroom house in Chincoteague

15. Come out and enjoy Autumn at the HH Ranch on Smith Island.

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

17. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

18. The Neigh-Neigh - Location! Location! Location!

19. Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

20. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Find holiday rentals that suit your style

Top Princess Anne Hotel Reviews

Blufin Bungalows & Marina

Find out more about Princess Anne

Princess Anne Holiday Homes information