Find hotels with pools in Anchorage, Annapolis from $85

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Check availability on Anchorage Hotels with a Pool

Our top choices for Anchorage hotels with a pool

Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
$136 nightly
The price is $149
Dec 21 - Dec 22
Total with taxes and fees
Rod 'N' Reel Resort
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (360)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
$120 nightly
The price is $132
Dec 14 - Dec 15
Total with taxes and fees
Knapps Narrows Marina & Inn
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (932)
"It was very comfortable and clean"
United States
Maria
$87 nightly
The price is $97
Jan 3 - Jan 4, 2026
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1000)
"clean and comfy, friendly staff"
United States
Tamara
$105 nightly
The price is $116
Dec 17 - Dec 18
Total with taxes and fees
St Michaels Inn
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1000)
"Excellent from check in to check out, highly recommend!"
United States
Eric
$110 nightly
The price is $125
Jan 10 - Jan 11, 2026
Total with taxes and fees
Crowne Plaza Annapolis by IHG
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
$179 nightly
The price is $195
Dec 14 - Dec 15
Total with taxes and fees
Kent Island Resort
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
$175 nightly
The price is $193
Jan 1 - Jan 2, 2026
Total with taxes and fees
Wylder Tilghman Island
Outdoor pool
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
$149 nightly
The price is $170
Dec 28 - Dec 29
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
Lobby
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (860)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
$85 nightly
The price is $94
Dec 14 - Dec 15
Total with taxes and fees
Quality Inn Grasonville near Kent Island
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, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
$74 nightly
The price is $85
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hilton Garden Inn Annapolis
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 Anchorage Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"This is a very nice hotel clean and seems to be new"
richard 1-night trip
Posted 2 days ago
Crowne Plaza Annapolis by IHG

Frequently asked questions

What are some accommodations with pools in Anchorage?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Offers buffet, an indoor pool, and free self parking. Microtel Inn & Suites by Wyndham Gambrills: Features buffet, a seasonal outdoor pool, and free self parking. Hilton Garden Inn Annapolis Downtown: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli.
What is there to see and do in Anchorage?
Make a point to visit attractions like Bay Ridge Beach and Annapolis Maritime Museum. Discover sights such as Maryland Quiet Waters Park, Annapolis Landing Marina, and Annapolis City Dock during your stay.
When is the best time to book a hotel with a pool in Anchorage?
You may want to consider a place to stay with an outdoor swimming pool if you plan to visit 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.

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