Sherwood Vacations

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Find the Best Sherwood Vacation Packages

Sherwood Hotel Deals

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood MD
10/10 Exceptional! (37 reviews)
What a spectacular home!! We all loved our stay and took advantage of the beautiful heated pool, dock, fire pit and playground. In the evening the pool table, ping pong and foosball were enjoyed by all. Stunning views, beautiful furnishings and comfortable bedding. Hopefully we will have occasion ...

Reviewed on Oct 20, 2025

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ¥11,782 per night from Feb 8 to Feb 9
¥11,782
¥13,432 total
Feb 8 - Feb 9
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Clean and we moved to a quiet room as well

Reviewed on Jan 8, 2026

DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ¥23,175 per night from Jan 21 to Jan 22
¥23,175
¥26,419 total
Jan 21 - Jan 22
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
Pleasant staff. Good location to walk to restaurants, shops.

Reviewed on Dec 30, 2025

Graduate by Hilton 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.