Princess Anne Holiday Houses

Princess Anne Holiday Homes
United States of America
Holiday Homes
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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 single-story house with a front porch, a door, and a mailbox.

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.

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

1. 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 NZ$655

NZ$655

includes taxes & fees

18 Oct - 19 Oct

Salisbury Hideaway

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

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

2. 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 NZ$429

NZ$429

includes taxes & fees

5 Oct - 6 Oct

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

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

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.

3. 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 NZ$329

NZ$329

includes taxes & fees

28 Sept - 29 Sept

Cottage near the Bay

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

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

A dining area with a wooden table and chairs, a hanging light fixture, and a kitchen in the background.

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

4. 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 NZ$614

NZ$614

includes taxes & fees

27 Oct - 28 Oct

Salisbury Cottage

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

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.

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

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 NZ$482

NZ$482

includes taxes & fees

28 Sept - 29 Sept

Cozy Barn Loft: Country Views & Central to Beaches

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

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

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 NZ$401

NZ$401

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 living room with a television, a white cabinet with gold handles, a lamp, and a dining area.

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.

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

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 NZ$558

NZ$558

includes taxes & fees

28 Sept - 29 Sept

Entire Private Home • Sleeps 6 • Prime Salisbury Location

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

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

A bedroom with a bed, a desk, a chair, a window, and a view of buildings.

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

8. 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 NZ$907

NZ$907

includes taxes & fees

1 Oct - 2 Oct

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 and a dock extending into the water.

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.

9. 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 NZ$794

NZ$794

includes taxes & fees

28 Sept - 29 Sept

The purple door at the bay.

A sandy beach with footprints and a person walking.

A view through a window of a building with a grassy area, a road, and a body of water in the background.

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.

10. 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 NZ$728

NZ$728

includes taxes & fees

28 Sept - 29 Sept

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

A covered porch with white wooden walls and large windows. There are two rocking chairs with floral cushions and a small table with a chair.

A modern kitchen with white cabinetry, a wooden accent wall, a built-in oven, and a large island with a bowl.

A two-story house with a red door, a front porch, and a tree in the foreground.

A covered porch with wooden furniture, including chairs and a table, and large windows along the walls.

11. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!

Up the Neck

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 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."

Katlyn

The price is NZ$603

NZ$603

includes taxes & fees

30 Sept - 1 Oct

2 Mi to Downtown: Tranquil Abode in Chincoteague!

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

A dining area with a wooden table set for four, white chairs, and a modern pendant light.

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

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

12. 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 NZ$527

NZ$527

includes taxes & fees

28 Sept - 29 Sept

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

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

A porch with a blue swing seat, two cushions, and a wooden bench.

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

13. 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 NZ$524

NZ$524

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 carpeted staircase with a wooden handrail, a wall-mounted air vent, and framed artwork.

A wooden deck with two chairs and a table.

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.

14. 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 NZ$565

NZ$565

includes taxes & fees

1 Oct - 2 Oct

Misty Mare Townhouse - Gorgeous home on Chincoteague 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 over a calm body of water, surrounded by trees and a clear sky.

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

15. 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 NZ$816

NZ$816

includes taxes & fees

5 Oct - 6 Oct

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

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

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

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

A covered porch with a sofa and chairs, a small table, and a wooden railing.

16. 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 NZ$537

NZ$537

includes taxes & fees

1 Oct - 2 Oct

Cozy 2-bedroom house in Chincoteague

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

A wooden deck with white railings, a door with a wreath, and two wicker chairs.

A kitchen with white cabinets, a black stove, a microwave, and a sink.

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

17. 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 NZ$562

NZ$562

includes taxes & fees

16 Oct - 17 Oct

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

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

A row of seaside cottages with a stone breakwater in front.

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.

18. 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.

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

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

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

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

A two-story building with a central tower, a front porch, and a gravel driveway.

19. 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 NZ$571

NZ$571

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

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

A cozy attic bedroom with a sloped ceiling, a large bed with a travel-themed duvet, a desk with a chair, and a window with a view.

20. 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 NZ$892

NZ$892

includes taxes & fees

1 Oct - 2 Oct

The Neigh-Neigh - Location! Location! 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.

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Top Princess Anne Hotel Reviews

Atlantic Shores Inn and Suites

8/10 Good

"I like a room that has separate bath & toilet ,so door allows roommate to use sink."

Lana 2-night trip

Posted 14 hours ago

Atlantic Shores Inn and Suites

Key West Cottages

10/10 Excellent

"This is a 10/10 stay. Beautiful cottages, amazing views. Location is pristine! Must book!"

Kayla 2-night trip

Posted 1 day ago

Key West Cottages

Courtyard by Marriott Salisbury

10/10 Excellent

"All satisfactory. Accommodations fine. Staff very efficient and friendly."

Michael 1-night trip

Posted 2 days ago

Courtyard by Marriott Salisbury

Blufin Bungalows & Marina

10/10 Excellent

"Loved it…what a fun experience!"

Wendy 3-night trip

Posted 3 days ago

Blufin Bungalows & Marina

Best Western Salisbury Plaza

8/10 Good

"I would have preferred non plastic plates and flatware"

Sarah 1-night trip

Posted 5 days ago

Best Western Salisbury Plaza

The Reserve Inn

10/10 Excellent

"Excellent 5 ✨✨✨✨"

Alba 1-night trip

Posted 7 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 10 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 11 days ago

Wingate by Wyndham Salisbury MD Airport North

Find out more about Princess Anne

Princess Anne Holiday Homes information

Number of reviews	695
Accommodation	632 Holiday Homes
Lowest Price	NZ$329
Highest Price	NZ$907

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Book Holiday Homes in Princess Anne on Expedia.com

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. Salisbury Hideaway

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

3. Cottage near the Bay

4. Salisbury Cottage

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

6. Blufin Bungalows & Marina

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

8. Bayfront Modern Retreat • Dock, Kayaks, Views

9. The purple door at the bay.

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

11. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

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

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

14. Misty Mare Townhouse - Gorgeous home on Chincoteague Island

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

16. Cozy 2-bedroom house in Chincoteague

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

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

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

20. The Neigh-Neigh - Location! Location! Location!

Find holiday rentals that suit your style

Top Princess Anne Hotel Reviews

Atlantic Shores Inn and Suites

Find out more about Princess Anne

Princess Anne Holiday Homes information

Explore a world of travel with Expedia