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Find Hotels with a Pool in Chester, MD

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Check availability on Chester Hotels with a Pool

This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Our top choices for Chester hotels with a pool

Indoor pool

1. Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (578 reviews)
  • cleanliness
    Dive into refreshing luxury at this Easton hotel with a pristine indoor pool and fitness center for your aquatic escape.
The price is NT$4,749
NT$5,224 total
includes taxes & fees
Aug 16 - Aug 17
Hampton Inn Easton
Seasonal outdoor pool

2. Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (910 reviews)
  • cleanliness
    Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center.
The price is NT$3,670
NT$4,037 total
includes taxes & fees
Aug 9 - Aug 10
Quality Inn
Indoor pool

3. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
The price is NT$4,513
NT$4,964 total
includes taxes & fees
Aug 6 - Aug 7
Best Western Plus Easton Inn & Suites
Indoor pool

4. Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (624 reviews)
  • cleanliness
    Splashy indoor pool retreat creates a refreshing escape in the heart of Easton.
The price is NT$5,032
NT$5,535 total
includes taxes & fees
Aug 9 - Aug 10
Holiday Inn Express Easton by IHG
Indoor pool

5. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (383 reviews)
  • cleanliness
    Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.
The price is NT$4,664
NT$5,130 total
includes taxes & fees
Aug 27 - Aug 28
Fairfield Inn & Suites by Marriott Easton
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

6. The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (43 reviews)
  • cleanliness
    Scenic waterfront pool creates a summer paradise with views and easy water access.
The price is NT$14,288
NT$15,717 total
includes taxes & fees
Aug 11 - Aug 12
The Oaks Waterfront
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

7. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is NT$2,893
NT$3,182 total
includes taxes & fees
Aug 23 - Aug 24
St Michaels Inn
Outdoor pool

8. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (395 reviews)
  • cleanliness
    Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.
The price is NT$20,161
NT$22,177 total
includes taxes & fees
Aug 23 - Aug 24
Inn at Perry Cabin
Exterior

9. George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (76 reviews)
  • cleanliness
    Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.
The price is NT$6,866
NT$7,553 total
includes taxes & fees
Aug 10 - Aug 11
George Brooks House B&B
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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Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars

Top Chester Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Super quiet. Great bed."
Gary 1-night trip
Posted 13 hours ago
Graduate by Hilton Annapolis

Frequently asked questions

What are some hotels with pools in Chester?
Historic Inns of Annapolis: Offers daily, a seasonal outdoor pool, and free self parking. St Michaels Inn: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Crowne Plaza Annapolis by IHG: Provides buffet, an indoor pool, and free self parking. Graduate by Hilton Annapolis: Offers a snack bar/deli, an indoor pool, and free self parking.
What is there to see and do in Chester?
Enjoy a stroll along the shore at Sandy Point Beach and Bay Ridge Beach. Discover sights such as Northern Chesapeake Bay, Matapeake State Park, and Chesapeake Bay Environmental Center during your stay.
When is the best time to book a hotel with a pool in Chester?
You may want to think about a place to stay with an outdoor swimming pool if you plan to visit Chester in the warmest months of July, August, or June when the average temperature is 74°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temp is 39°F.