When is the best time to go to Oyster Harbor?

The best time to visit Oyster Harbor is during the late spring and early autumn months, specifically May, early June, September, and October. These periods offer pleasant weather with comfortable temperatures, making it ideal for enjoying outdoor activities without the intense heat and humidity of mid-summer. You'll also find fewer crowds during these shoulder seasons, allowing for a more relaxed experience. Families looking for a classic beach holiday will find July and August suitable, although these months are the busiest and hottest. The water is warmest then, superb for swimming and watersports, and most attractions are in full swing. However, be prepared for larger crowds and higher accommodation prices. For those interested in fishing or boating, late spring and early autumn provide excellent conditions, with calmer waters and good catches.

Can I cancel my hotel reservation on Expedia?

Many Expedia hotel reservations are refundable, provided that you cancel before the hotel’s cancellation deadline − this is often within 24 to 48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our ‘Fully refundable property’ filter during your search to find the right Oyster Harbor hotel for you.

How can I save on a hotel booking in Oyster Harbor with Expedia?

One Key™ —Expedia’s free travel rewards program—gives you instant access to discounts with Member Prices on Oyster Harbor hotels. Plus, you’ll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Oyster Harbor?

Hotel prices in Oyster Harbor often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates and sort search results by ‘Price: low to high’ for our cheapest rates.

Oyster Harbor Hotels: Cheap Accommodation in Oyster Harbor

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 prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Oyster Harbor hotels

1. Laurel Grove Inn on the South

10.6 km from Oyster Harbor

Ruth

includes taxes & fees

12 Aug - 13 Aug

2. Historic Inns of Annapolis

Historic District, 6.2 km from Oyster Harbor

Monica

includes taxes & fees

25 Aug - 26 Aug

3. DoubleTree by Hilton Hotel Annapolis

9 km from Oyster Harbor

eliana

includes taxes & fees

30 Aug - 31 Aug

4. Hilton Garden Inn Annapolis Downtown

6.3 km from Oyster Harbor

Nelson

includes taxes & fees

30 Aug - 31 Aug

5. Fairfield Inn & Suites By Marriott Annapolis

6.7 km from Oyster Harbor

Eileen

includes taxes & fees

16 Aug - 17 Aug

6. SpringHill Suites by Marriott Annapolis

8.6 km from Oyster Harbor

Thomas

includes taxes & fees

30 Aug - 31 Aug

Room, 1 King Bed, Non Smoking (Whirlpool)

7. Holiday Inn Express & Suites Annapolis by IHG

8.8 km from Oyster Harbor

Jaime

includes taxes & fees

18 Aug - 19 Aug

8. Graduate by Hilton Annapolis

6.3 km from Oyster Harbor

MARIANNA

includes taxes & fees

31 Aug - 1 Sept

9. Country Inn & Suites by Radisson, Annapolis, MD

10 km from Oyster Harbor

Annapurna

includes taxes & fees

1 Sept - 2 Sept

10. The Westin Annapolis

6.4 km from Oyster Harbor

Jessica

includes taxes & fees

16 Aug - 17 Aug

11. Crowne Plaza Annapolis by IHG

9.3 km from Oyster Harbor

Douglas and Lori

includes taxes & fees

1 Sept - 2 Sept

12. Best Western Annapolis

9 km from Oyster Harbor

Julian

includes taxes & fees

30 Aug - 31 Aug

13. Residence Inn By Marriott Annapolis

6.7 km from Oyster Harbor

Caitlin

includes taxes & fees

23 Aug - 24 Aug

14. Hampton Inn & Suites Annapolis

8.7 km from Oyster Harbor

Meghalee

includes taxes & fees

26 Aug - 27 Aug

15. Courtyard by Marriott Annapolis

9.1 km from Oyster Harbor

Tyriek

includes taxes & fees

31 Aug - 1 Sept

16. Hilton Garden Inn Annapolis

9.1 km from Oyster Harbor

Glenn

includes taxes & fees

25 Aug - 26 Aug

17. Sonesta ES Suites Annapolis

8.8 km from Oyster Harbor

Daniela

includes taxes & fees

2 Sept - 3 Sept

Premium bedding, down duvets, pillow-top beds, in-room safe

18. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 5.7 km from Oyster Harbor

includes taxes & fees

23 Aug - 24 Aug

19. TownePlace Suites by Marriott Annapolis

8.9 km from Oyster Harbor

Jamila

includes taxes & fees

17 Aug - 18 Aug

20. Candlewood Suites Annapolis by IHG

8.5 km from Oyster Harbor

Javier

includes taxes & fees

23 Aug - 24 Aug

View all properties

Our guide on where to stay in Oyster Harbor

Find the best Oyster Harbor areas for the activities you enjoy most.

An aerial view of a coastal town with a prominent church, dense residential area, and a marina with boats.

Historic District

While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.

See properties

A marina with numerous sailboats docked, surrounded by residential houses and a backdrop of trees and a distant shoreline.

Eastport

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

See properties

A cityscape with historic buildings, a river, and a bridge in the background.

Murray Hill

If you're spending some time in Murray Hill, Spa Creek and Ballet Theater of Maryland are top sights worth seeing.

See properties

A large suspension bridge spanning a wide river at sunset.

Hillsmere

While visiting Hillsmere, you might make a stop by sights like Maryland Quiet Waters Park and Great Frogs Winery.

See properties

A suspension bridge over a body of water with a sunset in the background.

Cape Saint Claire

While visiting Cape Saint Claire, you might make a stop by sights like Northern Chesapeake Bay and Chesapeake Bay.

See properties

Top Oyster Harbor Hotel Reviews

Recent Reviews in Oyster Harbor

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"Room was clean. Staff were friendly. The area shuttle was a wonderful amenity to have access to with friendly drivers! The no my opportunity to note is the air conditioning was inconsistent getting very cold then cycling off to very warm making it hard to sleep comfortably during a summer stay."

Historic Inns of Annapolis

8/10 Good

"Our stay was overall good. The room stayed cool during a very hot weekend. It is so conveniently located! Our only opportunity to note is that our housekeeping was inconsistent. Day 2 we were in the room and we asked if the house keeper could come back. They never came back. Day 3 the house keeper came late into the afternoon (after not coming the day prior) and straightened the bed and took most of the trash out but not all of it, and changed out the towels. The coffee station was not refilled. We are low maintenance as far as having new towels, etc. but we did have quite a bit of trash and recycling that would have been nice to not stack up. We have stayed here twice. If the prices is reasonable we will stay here again. Note: there is a small fitness room that we didn’t know existed. Not big but nice to know it is there for future stays."

Oyster Harbor Hotels, Annapolis

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Oyster Harbor hotels

1. Laurel Grove Inn on the South

2. Historic Inns of Annapolis

3. DoubleTree by Hilton Hotel Annapolis

4. Hilton Garden Inn Annapolis Downtown

5. Fairfield Inn & Suites By Marriott Annapolis

6. SpringHill Suites by Marriott Annapolis

7. Holiday Inn Express & Suites Annapolis by IHG

8. Graduate by Hilton Annapolis

9. Country Inn & Suites by Radisson, Annapolis, MD

10. The Westin Annapolis

11. Crowne Plaza Annapolis by IHG

12. Best Western Annapolis

13. Residence Inn By Marriott Annapolis

14. Hampton Inn & Suites Annapolis

15. Courtyard by Marriott Annapolis

16. Hilton Garden Inn Annapolis

17. Sonesta ES Suites Annapolis

18. Annapolis Waterfront Hotel, Autograph Collection

19. TownePlace Suites by Marriott Annapolis

20. Candlewood Suites Annapolis by IHG

Our guide on where to stay in Oyster Harbor

Historic District

Eastport

Murray Hill

Hillsmere

Cape Saint Claire

Top Oyster Harbor Hotel Reviews

Recent Reviews in Oyster Harbor

DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

Explore a world of travel with Expedia