The Best Hotels with a Pool in Princess Anne, MD from ₩97,084 in 2026

Q: What are some accommodations with pools in Princess Anne?

Econo Lodge Princess Anne : Features continental, a seasonal outdoor pool, and free self parking. Americas Best Value Inn Princess Anne : Provides daily, a seasonal outdoor pool, and free self parking. Waterside Inn : Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Chincoteague Inn : Offers daily, an indoor pool, and free self parking. Country Inn & Suites by Radisson, Salisbury, MD : Features a snack bar/deli, a seasonal outdoor pool, and daily.

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Our top choices for Princess Anne hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by a building with multiple balconies.

1. Econo Lodge Princess Anne

Princess Anne

Bask in the sun at this charming motel with a seasonal outdoor pool, loungers for relaxing, and complimentary breakfast.

₩107,763 total

includes taxes & fees

Dec 1 - Dec 2

A modern indoor pool area with wooden beams, a pool, and seating arrangements.

2. Hampton Inn & Suites Salisbury/Fruitland

Fruitland

Splash into relaxation at this spotless hotel, featuring a sunlit indoor pool and inviting hot tub.

₩165,044 total

includes taxes & fees

Nov 29 - Nov 30

An indoor swimming pool with a clear view of the pool area, including the poolside seating and the adjacent room with a large window.

3. Home2 Suites By Hilton Salisbury Fruitland

Fruitland

₩165,360 total

includes taxes & fees

Nov 23 - Nov 24

An indoor swimming pool with lounge chairs and a ceiling with cloud designs.

4. Best Western Plus Pocomoke City

Pocomoke City

Sparkling indoor pool creates year-round relaxation oasis at this charming rural retreat.

₩144,390 total

includes taxes & fees

Dec 6 - Dec 7

A hotel with a swimming pool, lounge chairs, and a covered outdoor seating area.

5. Wingate by Wyndham Salisbury MD Airport North

Salisbury

Splash into relaxation at the seasonal pool with loungers for effortless summer unwinding.

₩134,593 total

includes taxes & fees

Dec 6 - Dec 7

An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables.

6. Country Inn & Suites by Radisson, Salisbury, MD

Salisbury

Dive into aquatic bliss at this hotel's indoor pool and hot tub sanctuary, perfect for year-round relaxation and fitness.

₩125,231 total

includes taxes & fees

Dec 6 - Dec 7

An indoor swimming pool with clear lanes, a lifeguard chair, and a sun lounger by the poolside.

7. Courtyard by Marriott Salisbury

Salisbury

Sink into serenity at this modern hotel's indoor pool sanctuary, where bubbling hot tub escapes and extended swimming hours await.

₩159,275 total

includes taxes & fees

Dec 11 - Dec 12

A swimming pool with lounge chairs and a covered seating area, surrounded by a building with multiple balconies and lighting.

8. Best Western Salisbury Plaza

Salisbury

Dive into the seasonal outdoor pool surrounded by loungers and umbrellas for a refreshing summer retreat in Salisbury.

₩128,363 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with a covered area and lounge chairs, a Marriott Residence Inn building, and a 'No Diving' sign.

9. Residence Inn by Marriott Salisbury

Salisbury

Dive into seasonal pool perfection at this modern Salisbury hotel with hot tub relaxation and fitness options.

₩174,750 total

includes taxes & fees

Dec 6 - Dec 7

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

10. Comfort Suites Chincoteague Island Bayfront Resort

Downtown Chincoteague

Sun-kissed indoor and outdoor pools with bayfront views await after a day of coastal fun.

₩151,125 total

includes taxes & fees

Dec 7 - Dec 8

View all properties

Choose what matters most at hotels with a pool in Princess Anne

Breakfast included

Hot tub

Top Princess Anne Hotel Reviews

Hampton Inn & Suites Salisbury/Fruitland

Fruitland

10/10 Excellent

Anonymous traveler

Courtyard by Marriott Salisbury

Salisbury

10/10 Excellent

Tonya

Wingate by Wyndham Salisbury MD Airport North

Salisbury

10/10 Excellent

Monica

An indoor swimming pool with clear blue water, surrounded by large windows and sunlit seating areas.

Hampton Inn & Suites Chincoteague Waterfront

Downtown Chincoteague

10/10 Excellent

Hampton Inn is our go-to family hotel, so we've stayed in a bunch, and several have been really nice. This one is the cleanest, friendliest, most-beautifully set we have stayed at. The view from our balcony was amazing. My 5 year old saw her first jelly fish and dolphins swimming in the channel, from our balcony. The beds were very comfortable - there was even a good night light in the bathroom. The breakfast was very well stocked, well managed, and there was plenty of seating, again, with...

Kate

Comfort Suites Chincoteague Island Bayfront Resort

Downtown Chincoteague

10/10 Excellent

Tatyana

A row of colorful cabins with a swimming pool in the foreground.

Key West Cottages

Downtown Chincoteague

10/10 Excellent

Chris

A pool with clear blue water, surrounded by lounge chairs and umbrellas, with a view of the ocean.

Blufin Bungalows & Marina

Down the Marsh

10/10 Excellent

Richard

Residence Inn by Marriott Salisbury

Salisbury

10/10 Excellent

Meghan

A deck with outdoor seating and umbrellas, overlooking a pool.

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Downtown Chincoteague

10/10 Excellent

I was looking for a place to stay in Chincoteague, Va. My youngest son and his wife were coming from Northern Virginia to meet me and my wife coming from Virginia Beach, Virginia. Our goal was to show my son's wife the wild ponies of Assateague Island. Also the statue of "Misty of Chincoteague" in the local park. Staying at the Fairfield Inn allowed us to get to the park area very quickly. On the last day of our stay we were able to see the ponies, take photos, and enjoy the park. We returned...

Bill

Country Inn & Suites by Radisson, Salisbury, MD

Salisbury

10/10 Excellent

Jean yvens

A swimming pool with a white deck, a metal ladder, and a white picket fence.

Garden and Sea Inn

New Church

10/10 Excellent

larry

A swimming pool with a view of the water, a deck with lounge chairs, and a fence.

Waterside Inn

Downtown Chincoteague

10/10 Excellent

Matthew

A swimming pool with lounge chairs and a view of the sunset over the water.

Marina Bay Hotel & Suites, an Ascend Collection Hotel

Downtown Chincoteague

10/10 Excellent

Matthew

A swimming pool with lounge chairs and a fenced area, surrounded by a building with multiple balconies.

Rodeway Inn at Somers Cove Marina

Crisfield

10/10 Excellent

Dominick

Frequently Asked Questions

What are some accommodations with pools in Princess Anne?

Econo Lodge Princess Anne: Features continental, a seasonal outdoor pool, and free self parking. Americas Best Value Inn Princess Anne: Provides daily, a seasonal outdoor pool, and free self parking. Waterside Inn: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Chincoteague Inn: Offers daily, an indoor pool, and free self parking. Country Inn & Suites by Radisson, Salisbury, MD: Features a snack bar/deli, a seasonal outdoor pool, and daily.

What is there to see and do in Princess Anne?

Make a point to visit attractions like Mount Vernon Beach and Manokin Park. During your stay, check out sights such as Hytche athletic Center, Somerset County Library, and Princess Anne Town Hall. You'll also discover lots of options for restaurants in Princess Anne.

When is the best time to book a hotel with a pool in Princess Anne?

You may want to consider a place to stay that offers an outdoor pool if you plan to visit Princess Anne in the hottest months of July, August, or June when the average temp is 75°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 42°F.

Find Hotels with a Pool in Princess Anne, MD

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Treat yourself

Be picky

Check prices for these dates

Our top choices for Princess Anne hotels with a pool

1. Econo Lodge Princess Anne

2. Hampton Inn & Suites Salisbury/Fruitland

3. Home2 Suites By Hilton Salisbury Fruitland

4. Best Western Plus Pocomoke City

5. Wingate by Wyndham Salisbury MD Airport North

6. Country Inn & Suites by Radisson, Salisbury, MD

7. Courtyard by Marriott Salisbury

8. Best Western Salisbury Plaza

9. Residence Inn by Marriott Salisbury

10. Comfort Suites Chincoteague Island Bayfront Resort

Choose what matters most at hotels with a pool in Princess Anne

Top Princess Anne Hotel Reviews

Hampton Inn & Suites Salisbury/Fruitland

10/10 Excellent

Frequently Asked Questions

What are some accommodations with pools in Princess Anne?

What is there to see and do in Princess Anne?

When is the best time to book a hotel with a pool in Princess Anne?