Winery Hotels in Princess Anne
Maryland
United States of America
Winery Hotels
Expedia.ae

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

Find Winery Hotels in Princess Anne, MD

Where to?

Dates

your current months are November, 2026 and December, 2026.

November 2026

SunSunday

MonMonday

TueTuesday

WedWednesday

ThuThursday

FriFriday

SatSaturday

December 2026

SunSunday

MonMonday

TueTuesday

WedWednesday

ThuThursday

FriFriday

SatSaturday

Travelers

Room 1

Adults

ChildrenAges 0 to 17

Need to book 9 or more rooms?

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Princess Anne hotels with winery

A large, historic house with a wrap-around porch and a gazebo, surrounded by lush vegetation and a body of water.

A covered porch with wicker furniture, a small table, and a view of a green landscape and water.

A river with a dock, a sailboat, and a motorboat. There are buildings and trees in the background.

A window with a view of a body of water, dock, and grassy area.

1. The Whitehaven Hotel

The Whitehaven Hotel

3.5 star property

Quantico

10.0 out of 10, Exceptional, (139 reviews)

10/10

Exceptional

(139 reviews)

"Wonderful hosts, clean, historic hotel, quiet, beautiful view, delicious breakfast."

Tracy

The price is AED 487

AED 487

AED 545 total

includes taxes & fees

10 Nov - 11 Nov

The Whitehaven Hotel

A modern hotel lobby with a blue sofa, white ottomans, and a dining area with tables and chairs.

A hotel room with a bed, bedside table, and a desk with a chair.

A modern lounge area with a stone pillar, grey sofa, and a fireplace.

A hotel lobby with a reception desk, seating area, and a view of the outdoors.

2. Best Western Salisbury Plaza

Best Western Salisbury Plaza

2.5 star property

Salisbury

6.4 out of 10, (1,002 reviews)

6.4/10

(1,002 reviews)

"clean, pleasant and helpful front desk person, parking convenient, comfortable bed. There was no hand lotion as an amenity so I am glad I had some with me."

Charleen

The price is AED 313

AED 313

AED 351 total

includes taxes & fees

11 Nov - 12 Nov

Best Western Salisbury Plaza

A large, multi-story Victorian-style house with a prominent tower and a wrap-around porch.

A grand staircase with ornate woodwork, a fireplace with a checkered floor, and a cozy seating area with a lamp.

A room with a wooden cabinet, two upholstered chairs, a radiator, and a stained glass window.

A traditional living room with a fireplace, ornate furniture, and stained glass windows.

3. Gillis Grier Bed & Breakfast

Gillis Grier Bed & Breakfast

3.0 star property

Salisbury

10.0 out of 10, Exceptional, (205 reviews)

10/10

Exceptional

(205 reviews)

"A delightful visit will be assured with a visit here. The proprietors are kind and informative. The breakfast was exquisite. If you are an avid B and B guest, don’t miss the chance to experience this home."

Devra

The price is AED 612

AED 612

AED 685 total

includes taxes & fees

10 Nov - 11 Nov

Gillis Grier Bed & Breakfast

A waterfront hotel with a wooden deck, grassy lawn, and multiple balconies.

A beach with wide sandy shores and gentle waves.

A multi-story hotel with a 'Comfort Suites' sign, featuring balconies and a well-maintained lawn.

An indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

4. Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort

2.5 star property

Downtown Chincoteague

9.6 out of 10, Exceptional, (1,004 reviews)

9.6/10

Exceptional

(1,004 reviews)

"Best room on the island"

Jeffrey

The price is AED 364

AED 364

AED 413 total

includes taxes & fees

29 Nov - 30 Nov

Comfort Suites Chincoteague Island Bayfront Resort

A beach with waves gently lapping onto the shore under a clear sky.

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

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.

5. Salisbury Hideaway

Salisbury Hideaway

Salisbury

10.0 out of 10, Exceptional, (24 reviews)

10/10

Exceptional

(24 reviews)

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

Michelle S.

The price is AED 507

AED 507

AED 1,215 total

includes taxes & fees

1 Dec - 2 Dec

Salisbury Hideaway

An outdoor seating area with a view of a waterfront during sunset.

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

A spacious living area with a large window, a ceiling fan, and a dining area.

A waterfront property with a dock, boats, and houses.

6. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views

Captain's Cove

9.8 out of 10, Exceptional, (73 reviews)

9.8/10

Exceptional

(73 reviews)

"We absolutely love staying here! "

Maggie G.

The price is AED 393

AED 393

AED 1,507 total

includes taxes & fees

16 Nov - 17 Nov

Bayfront Modern Retreat • Dock, Kayaks, Views

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

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.

A dining room with a wooden table set for six, surrounded by chairs.

7. 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)

"Everything was perfect! We loved the location and the house. Secluded but not too far from everything. The house was clean and very comfortable."

Debbie M.

The price is AED 485

AED 485

AED 1,508 total

includes taxes & fees

18 Nov - 19 Nov

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

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.

View all properties

Top Princess Anne Hotel Reviews

The Whitehaven Hotel

Quantico

10/10 Excellent

BEAUTIFUL. PEACEFUL. GRACIOUS HOSTESS. WE HIGHLY RECOMMEND. AND IF YOU ARE COMING UP HWY. 13 from VA. BE SURE TO TAKE FERRY. SAVES TIME AND IS AN EXPERIENCE.

Anonymous traveler

Reviewed April 22, 2021Reviewed April 22, 2021

The Whitehaven Hotel

Gillis Grier Bed & Breakfast

Salisbury

10/10 Excellent

Great hospitality and hosts, thanks.

Eric

Reviewed July 7, 2024Reviewed July 7, 2024

Gillis Grier Bed & Breakfast

Comfort Suites Chincoteague Island Bayfront Resort

Downtown Chincoteague

10/10 Excellent

Nice, clean, and big room. Good buffet, nice location

Tatyana

Reviewed January 12, 2023Reviewed January 12, 2023

Comfort Suites Chincoteague Island Bayfront Resort

Explore a world of travel with Expedia

Lodging
Flights
Packages

Hotels near Nutter's Crossing Golf Club
Standard Link for Hotels near Nutter's Crossing Golf Club
Adventure Hotels in Deal Island
Standard Link for Adventure Hotels in Deal Island
Lodges in Eastern Maryland
Standard Link for Lodges in Eastern Maryland
Cottages in Westover
Standard Link for Cottages in Westover
Casino Hotels in Berlin
Standard Link for Casino Hotels in Berlin
5 Star Hotels in Westover
Standard Link for 5 Star Hotels in Westover
Independent Hotels in Pocomoke City
Standard Link for Independent Hotels in Pocomoke City
Apartments in Whitehaven
Standard Link for Apartments in Whitehaven
B&B in Quantico
Standard Link for B&B in Quantico
Wyndham Extra Holidays Hotels in Eastern Maryland
Standard Link for Wyndham Extra Holidays Hotels in Eastern Maryland
Hotels with smoking rooms in Eastern Maryland
Standard Link for Hotels with smoking rooms in Eastern Maryland
Golf Hotels in Berlin
Standard Link for Golf Hotels in Berlin
Hotels with Free Parking in Whaleyville
Standard Link for Hotels with Free Parking in Whaleyville
5 Star Hotels in Whitehaven
Standard Link for 5 Star Hotels in Whitehaven
Hotels with Bars in West Ocean City
Standard Link for Hotels with Bars in West Ocean City
Marriott Hotels & Resorts in Pocomoke City
Standard Link for Marriott Hotels & Resorts in Pocomoke City
5 Star Hotels in Fruitland
Standard Link for 5 Star Hotels in Fruitland
Hotels with Early Check-in in Salisbury
Standard Link for Hotels with Early Check-in in Salisbury
Hotel Wedding Venues Hotels in Marion Station
Standard Link for Hotel Wedding Venues Hotels in Marion Station
Hotels with Free Parking in Cambridge
Standard Link for Hotels with Free Parking in Cambridge
Motel 6 Hotels in Westover
Standard Link for Motel 6 Hotels in Westover
Wyndham Hotels in Salisbury
Standard Link for Wyndham Hotels in Salisbury
Pocomoke City Hotels
Standard Link for Pocomoke City Hotels
5 Star Hotels in Salisbury
Standard Link for 5 Star Hotels in Salisbury
3 Star Hotels in Salisbury
Standard Link for 3 Star Hotels in Salisbury
Historic Hotels in Snow Hill
Standard Link for Historic Hotels in Snow Hill
Beach Hotels in Delmar
Standard Link for Beach Hotels in Delmar
Cheap Hotels in Delmar
Standard Link for Cheap Hotels in Delmar
Marriott Hotels & Resorts in Westover
Standard Link for Marriott Hotels & Resorts in Westover
Casino Hotels in Cambridge
Standard Link for Casino Hotels in Cambridge
Hotel Wedding Venues Hotels in Ocean City
Standard Link for Hotel Wedding Venues Hotels in Ocean City
Hilton Hotels in Marion Station
Standard Link for Hilton Hotels in Marion Station
Hotels with Bars in Fruitland
Standard Link for Hotels with Bars in Fruitland
Marriott Hotels & Resorts in Salisbury
Standard Link for Marriott Hotels & Resorts in Salisbury
Historic Hotels in Ocean Pines
Standard Link for Historic Hotels in Ocean Pines
Hotels with Free Parking in Salisbury
Standard Link for Hotels with Free Parking in Salisbury
Motel 6 Hotels in Salisbury
Standard Link for Motel 6 Hotels in Salisbury
Hotels near University of Maryland Eastern Shore
Standard Link for Hotels near University of Maryland Eastern Shore
Best Western Hotels in Whitehaven
Standard Link for Best Western Hotels in Whitehaven
B&B in Fruitland
Standard Link for B&B in Fruitland
Apartments in Quantico
Standard Link for Apartments in Quantico
Hotels with Hot Tubs in Berlin
Standard Link for Hotels with Hot Tubs in Berlin
Best Western Hotels in Fruitland
Standard Link for Best Western Hotels in Fruitland
Adventure Hotels in Eastern Maryland
Standard Link for Adventure Hotels in Eastern Maryland
Cottages in Whitehaven
Standard Link for Cottages in Whitehaven
4 Star Hotels in Quantico
Standard Link for 4 Star Hotels in Quantico
Hotels with Bars in Princess Anne
Standard Link for Hotels with Bars in Princess Anne
Apartments in Salisbury
Standard Link for Apartments in Salisbury
Family Hotels in Ocean City
Standard Link for Family Hotels in Ocean City
Rv Parks in Eden
Standard Link for Rv Parks in Eden
Cottages in Quantico
Standard Link for Cottages in Quantico
Romantic Hotels in Fishing Creek
Standard Link for Romantic Hotels in Fishing Creek
Cottages in Salisbury
Standard Link for Cottages in Salisbury
Business Hotels in Ocean Pines
Standard Link for Business Hotels in Ocean Pines
Villas in Marion Station
Standard Link for Villas in Marion Station
2 Star Hotels in Salisbury
Standard Link for 2 Star Hotels in Salisbury
5 Star Hotels in Marion Station
Standard Link for 5 Star Hotels in Marion Station
Wyndham Hotels in Princess Anne
Standard Link for Wyndham Hotels in Princess Anne
B&B in Whitehaven
Standard Link for B&B in Whitehaven
Historic Hotels in Deal Island
Standard Link for Historic Hotels in Deal Island
Cabin Rentals in Salisbury
Standard Link for Cabin Rentals in Salisbury
Adventure Hotels in Ocean City
Standard Link for Adventure Hotels in Ocean City
Independent Hotels in Whitehaven
Standard Link for Independent Hotels in Whitehaven
Hilton Hotels in Eden
Standard Link for Hilton Hotels in Eden
B&B in Marion Station
Standard Link for B&B in Marion Station
Luxury Hotels in Ocean City
Standard Link for Luxury Hotels in Ocean City
Resorts & Hotels with Spas in Scotland
Standard Link for Resorts & Hotels with Spas in Scotland
Hotels with Hot Tubs in Cambridge
Standard Link for Hotels with Hot Tubs in Cambridge
Hotels with WiFi in West Ocean City
Standard Link for Hotels with WiFi in West Ocean City
Family Hotels in Berlin
Standard Link for Family Hotels in Berlin

Flights from Portland (PWM) to Salisbury (SBY)
Standard Link for Flights from Portland (PWM) to Salisbury (SBY)
Flights from Bergen (BGO) to Salisbury (SBY)
Standard Link for Flights from Bergen (BGO) to Salisbury (SBY)
Flights from Kodiak (ADQ) to Salisbury (SBY)
Standard Link for Flights from Kodiak (ADQ) to Salisbury (SBY)
Flights from Port Protection (PPV) to Salisbury (SBY)
Standard Link for Flights from Port Protection (PPV) to Salisbury (SBY)
Flights from Salisbury
Standard Link for Flights from Salisbury
Flights from Boston (BNH) to Salisbury (SBY)
Standard Link for Flights from Boston (BNH) to Salisbury (SBY)
Flights from Altoona (AOO) to Salisbury (SBY)
Standard Link for Flights from Altoona (AOO) to Salisbury (SBY)
Flights from Linz (LNZ) to Salisbury (SBY)
Standard Link for Flights from Linz (LNZ) to Salisbury (SBY)
Flights from Salzburg (SZG) to Salisbury (SBY)
Standard Link for Flights from Salzburg (SZG) to Salisbury (SBY)
Flights from Westover
Standard Link for Flights from Westover
Flights from Pendleton (PDT) to Salisbury (SBY)
Standard Link for Flights from Pendleton (PDT) to Salisbury (SBY)
Flights from Lynchburg (LYH) to Salisbury (SBY)
Standard Link for Flights from Lynchburg (LYH) to Salisbury (SBY)
Flights from Champaign (CMI) to Salisbury (SBY)
Standard Link for Flights from Champaign (CMI) to Salisbury (SBY)
Flights from Santiago (SCL) to Salisbury (SBY)
Standard Link for Flights from Santiago (SCL) to Salisbury (SBY)
Flights from Quantico
Standard Link for Flights from Quantico
Flights from San Luis Obispo (SBP) to Salisbury (SBY)
Standard Link for Flights from San Luis Obispo (SBP) to Salisbury (SBY)
Flights from Okayama (OKJ) to Salisbury (SBY)
Standard Link for Flights from Okayama (OKJ) to Salisbury (SBY)
Flights from Hamburg (HAM) to Salisbury (SBY)
Standard Link for Flights from Hamburg (HAM) to Salisbury (SBY)
Flights from Macon (MCN) to Salisbury (SBY)
Standard Link for Flights from Macon (MCN) to Salisbury (SBY)
Flights from Jiamusi (JMU) to Salisbury (SBY)
Standard Link for Flights from Jiamusi (JMU) to Salisbury (SBY)
Flights from Miami (MIA) to Salisbury (SBY)
Standard Link for Flights from Miami (MIA) to Salisbury (SBY)
Flights from Milwaukee (MKE) to Salisbury (SBY)
Standard Link for Flights from Milwaukee (MKE) to Salisbury (SBY)
Flights from Rotterdam (RTM) to Salisbury (SBY)
Standard Link for Flights from Rotterdam (RTM) to Salisbury (SBY)
Flights to Princess Anne
Standard Link for Flights to Princess Anne
Flights from Provo (PVU) to Salisbury (SBY)
Standard Link for Flights from Provo (PVU) to Salisbury (SBY)
Flights from New Bedford (EWB) to Salisbury (SBY)
Standard Link for Flights from New Bedford (EWB) to Salisbury (SBY)
Flights from Eagle (EAA) to Salisbury (SBY)
Standard Link for Flights from Eagle (EAA) to Salisbury (SBY)
Flights from Bagdogra (IXB) to Salisbury (SBY)
Standard Link for Flights from Bagdogra (IXB) to Salisbury (SBY)
Flights from Fruitland
Standard Link for Flights from Fruitland

Salisbury Vacations
Standard Link for Salisbury Vacations

Find Winery Hotels in Princess Anne, MD

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Princess Anne hotels with winery

1. The Whitehaven Hotel

2. Best Western Salisbury Plaza

3. Gillis Grier Bed & Breakfast

4. Comfort Suites Chincoteague Island Bayfront Resort

5. Salisbury Hideaway

6. Bayfront Modern Retreat • Dock, Kayaks, Views

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

Top Princess Anne Hotel Reviews

The Whitehaven Hotel

10/10 Excellent

Explore a world of travel with Expedia