Find Hotels with a Pool in Rose Haven, MD

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 availability on Rose Haven Hotels with a Pool

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Rose Haven hotels with a pool

Outdoor pool
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (372)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is ₩752,547
₩910,582 total
includes taxes & fees
Dec 30 - Dec 31
Inn at Perry Cabin
Porch
Parsonage Inn

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is ₩245,082
₩269,590 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Parsonage Inn
Exterior
George Brooks House B&B

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is ₩220,574
₩242,631 total
includes taxes & fees
Jan 1 - Jan 2, 2026
George Brooks House B&B
Seasonal outdoor pool, pool umbrellas
The Tilghman Island Inn

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is ₩295,540
₩325,094 total
includes taxes & fees
Jan 18 - Jan 19, 2026
The Tilghman Island Inn
Seasonal outdoor pool, sun loungers
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1005)
"Perfect "
United States
Coleen
The price is ₩122,945
₩140,157 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hampton Inn & Suites Annapolis
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1002)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
The price is ₩114,179
₩130,164 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hilton Garden Inn Annapolis
Indoor pool
Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG
2.5 star property
Prince Frederick
8.8 out of 10, Excellent, (698)
"Great environment, friendly staff, great place to stay with family and lots of things to do around the area!"
United States
Rosemary
The price is ₩148,491
₩180,827 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Holiday Inn Express Prince Frederick by IHG
Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1006)
"Cookies and coffee at check in .excellent staff "
United States
Cheryl
The price is ₩134,939
₩153,831 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Country Inn & Suites by Radisson, Annapolis, MD
View from property
The Westin Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1003)
"Beautiful and perfect location"
United States
Lauren
The price is ₩200,391
₩228,445 total
includes taxes & fees
Dec 30 - Dec 31
The Westin Annapolis
Seasonal outdoor pool, pool umbrellas, sun loungers
The Inn at Tacaro Estate

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (11)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The Inn at Tacaro Estate
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 Rose Haven Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Yes!"
Laurie 2-night trip
Posted 2 days ago
Crowne Plaza Annapolis by IHG

Frequently asked questions

What are some hotels with pools in Rose Haven?
DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Offers buffet, an indoor pool, and free self parking. Crowne Plaza Annapolis by IHG: Provides buffet, a seasonal outdoor pool, and free self parking. Graduate by Hilton Annapolis: Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. Annapolis Waterfront Hotel, Autograph Collection: Offers buffet, a seasonal outdoor pool, and complimentary wired internet access.
What is there to see and do in Rose Haven?
Make a point to visit attractions like Breezy Point Beach and Chesapeake Beach Water Park. During your stay, check out sights such as Rod n Reel Charter Fishing, Chesapeake Beach Railway Museum, and Bruce Gabrielson's Surf Art Gallery and Museum.
When is the best time to book a hotel with a pool in Rose Haven?
You may want to consider a place to stay with an outdoor swimming pool if you will be visiting Rose Haven 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 are visiting during the coldest months of January, February, or December when the average temp is 40°F.