Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Hotels

Estimated price for 1 night/2 adults

Get Rates
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4.0 out of 5.0 100 Heron Blvd Cambridge MD
8.8/5
(1002 Reviews)
Free Cancellation
Hyatt Regency Chesapeake Bay features a private beach, a golf course, and a marina. A stay here includes free parking. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, tours or tickets, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a full-service spa, 2 outdoor pools, and an indoor pool.
Reviewed on Jun 1, 2026

The service was exceptional.

Get Rates
Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5.0 2917 Ocean Gateway Cambridge MD
6.6/5
(1002 Reviews)
Free Cancellation
Guest of Days Inn & Suites by Wyndham Cambridge enjoy features like conference space, a 24-hour business center, and a seasonal outdoor pool. You can put free parking to good use if you drive. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include laundry facilities, a vending machine, and a reception hall.
Reviewed on May 29, 2026

I booked this place last minute just to spend a quick night after a change of plans in our trip due to weather. The place is simply disgusting. Don’t stay here. I never thought a Wyndham branded property could be this filthy. Shame on them for not verifying the basic cleanliness of a hotel they allow ...

Get Rates
Holiday Inn Express Cambridge by IHG

Holiday Inn Express Cambridge by IHG

2.5 out of 5.0 2715 Ocean Gtwy Cambridge MD
8.8/5
(779 Reviews)
Guests staying at Holiday Inn Express Cambridge by IHG enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and securing valuables. Additional amenities include a hot tub, conference space, and a 24-hour business center.
Reviewed on May 17, 2026

A very clean and wonderful hotel with helpful and friendly service staff. The breakfast bar was well stocked, and the rooms were spacious and clean. The hotel lobby was clean and the hotel itself was well kept. I would stay here again.

Get Rates
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 out of 5.0 2936 Ocean Gtwy Cambridge MD
8.2/5
(845 Reviews)
Free Cancellation
Guests of Comfort Inn & Suites Cambridge have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk is staffed 24/7 to help with luggage storage, and answer any questions about the accommodations. Additional amenities include meeting rooms, a business center, and a computer station.
Reviewed on Jun 1, 2026

Staff was excellent, rooms very clean good working refrigerator. Bed slept well. It was a wonderful 3 day stay I would definitely go back

Get Rates
Cambridge Inn

Cambridge Inn

2.0 out of 5.0 2831 Ocean Gateway Cambridge MD
5.4/5
(561 Reviews)
Free Cancellation
At Cambridge Inn, guests have access to free WiFi in public areas, coffee in a common area, and express check-out. There's free parking if you drive. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing. Additional amenities include laundry facilities and a vending machine.
Reviewed on May 30, 2026

BEDBUGS!! Staff was indifferent said you had 15minutes after check-in to report issues for refund on room.

Get Rates
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 out of 5.0 3206 Main St Grasonville MD
9/5
(1002 Reviews)
Guests staying at Hilton Garden Inn Kent Island Marina enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include meeting rooms, a business center, and a computer station.
Reviewed on May 31, 2026

The hotel was clean and looked nice, the bed was very soft in the middle and uncomfortable and the $14 breakfast was no where near worth it.

Get Rates
Robert Morris Inn

Robert Morris Inn

3.0 out of 5.0 314 N. Morris St Oxford MD
8.4/5
(280 Reviews)
Robert Morris Inn features free WiFi in public areas, conference space, and a business center. Free parking is available if you drive. Helpful staff can provide concierge services and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach bed & breakfast include a computer station, a library, and a terrace.
Reviewed on Feb 11, 2024

Beautiful resort, outdated but clean. We went on the weekend before ownership changed so the menu was limited and the breakfast was undercooked but the server was AWESOME! He remembered us and catered to us like we were the only customers.

Get Rates
Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5.0 155 Holiday Dr. P.O. Box 1099 Solomons MD
8/5
(996 Reviews)
Guests of Solomons Inn Resort & Marina have access to an outdoor pool, a gym, and a sauna. There's free parking and an airport shuttle. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and securing valuables. Additional amenities include free WiFi in public areas, an outdoor tennis court, and meeting rooms.
Reviewed on Mar 10, 2026

We arrived at the property to find it was closed. No advanced notice. We had called the hotel several times to alert them that we would not arrive until after 8, phone message said they were busy helping other customers or had stepped away from the desk. Had to find another hotel at 8:30 on a Friday ...

Get Rates
Hilton Garden Inn Solomons

Hilton Garden Inn Solomons

3.0 out of 5.0 13100 Dowell Road Solomons MD
8.6/5
(671 Reviews)
Free Cancellation
At Hilton Garden Inn Solomons, guests enjoy features like an outdoor pool, a 24-hour gym, and free WiFi in public areas. Self parking is available for USD 3.87 per day. The 24-hour front desk has staff standing by to help with luggage storage and securing valuables. Additional amenities include a 24-hour business center, express check-in, and express check-out.
Reviewed on May 31, 2026

Great Staff really helpful

Get Rates
Wingate by Wyndham North East

Wingate by Wyndham North East

3.0 out of 5.0 39 Elwoods Rd North East MD
8.2/5
(1006 Reviews)
Free Cancellation
Wingate by Wyndham North East features a gym, free WiFi in public areas, and conference space. If you drive, put free parking to good use. The 24-hour front desk has staff standing by to help with securing valuables and luggage storage. Additional amenities include a business center, a microwave in a common area, and a computer station.
Reviewed on May 31, 2026

The front desk was very friendly. Room was very clean and beds were comfortable. Breakfast has limited variety of food and can be improved.

Get Rates
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5.0 150 Scheeler Road Chestertown MD
8.6/5
(916 Reviews)
Free Cancellation
Comfort Inn & Suites Chestertown features a gym, free WiFi in public areas, and a business center. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.
Reviewed on May 28, 2026

my favorite place to stay when going to Chestertown. Recommend this hotel vs any other in the area

Get Rates
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

2.5 out of 5.0 101 Vfw Ave Grasonville MD
7.8/5
(913 Reviews)
Free Cancellation
Quality Inn Grasonville near Kent Island features free WiFi in public areas, a seasonal outdoor pool, and coffee in a common area. If you drive, take advantage of free parking. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Additional amenities include a computer station and a vending machine.
Reviewed on May 29, 2026

Slipped in the shower because of lack of non skid. Traffic noise is crazy. Pool has unposted random hours determined by front staff. Staff doesnt seem to be on the same page about amentities

Get Rates
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 out of 5.0 1020 Kent Narrows Rd Grasonville MD
9.2/5
(1002 Reviews)
Free Cancellation
Guests of Holiday Inn Express Annapolis East-Kent Island by IHG enjoy access to free WiFi in public areas, meeting rooms, and conference space. If you drive, put free parking to good use. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a 24-hour business center, a seasonal outdoor pool, and a computer station.
Reviewed on May 31, 2026

Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again.

Get Rates
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 out of 5.0 3101 Main Street Grasonville MD
8/5
(1005 Reviews)
Free Cancellation
At Best Western Kent Narrows Inn, guests enjoy an indoor pool, a gym, and a sauna. There's free parking if you drive. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Additional amenities include free WiFi in public areas, a hot tub, and a 24-hour business center.
Reviewed on May 28, 2026

Good hotel for the price

Get Rates
Holiday Inn Express North East by IHG

Holiday Inn Express North East by IHG

2.5 out of 5.0 101 Hotel Plz North East MD
8.4/5
(576 Reviews)
Free Cancellation
Guests of Holiday Inn Express North East by IHG have access to an outdoor pool, a gym, and free WiFi in public areas. There's free parking if you drive. The 24-hour front desk has multilingual staff ready to help secure valuables, and answer any questions about the area. Additional amenities include a business center, a seasonal outdoor pool, and coffee/tea in a common area.
Reviewed on May 31, 2026

It was just overall a nice hotel.

Get Rates
Red Roof Inn Perryville

Red Roof Inn Perryville

2.0 out of 5.0 61 Heather Lane Perryville MD
9/5
(184 Reviews)
Free Cancellation
Guests of Red Roof Inn Perryville enjoy access to free WiFi in public areas, meeting rooms, and a 24-hour business center. If you plan to drive, free parking is available. The front desk is staffed 24/7 to help with locker space, and answer any questions about the accommodations. Additional amenities include coffee/tea in a common area, a meeting room, and a computer station.
Reviewed on May 26, 2026

Clean and perfect for one night stay. Would stay again!

Get Rates
Quality Inn Solomons - Beacon Marina

Quality Inn Solomons - Beacon Marina

2.5 out of 5.0 255 Lore Rd Solomons MD
7.6/5
(888 Reviews)
Free Cancellation
Guests of Quality Inn Solomons - Beacon Marina enjoy access to free WiFi in public areas, a business center, and a seasonal outdoor pool. You can put free parking to good use if you drive. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include coffee/tea in a common area, laundry facilities, and a vending machine.
Reviewed on May 28, 2026

This is the 3rd time we have stayed here. The rooms are always clean, staff friendly & helpful. Just some constructive comments, It is soon time for the Galway’s to be updated, the carpets are starting to show their age & the tub enclosure could use a facelift.

Get Rates
Comfort Inn & Suites North East

Comfort Inn & Suites North East

2.5 out of 5.0 1 Center Drive I 95 Exit 100 North East MD
8/5
(690 Reviews)
Free Cancellation
Guests of Comfort Inn & Suites North East have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. You can take advantage of free parking if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include conference space, a business center, and coffee/tea in a common area.
Reviewed on Jun 1, 2026

Our check in was easy and efficient. The hotel is a little outdated but the rooms were clean and common areas were well maintained. Our microwave didn't work in the room but staff were

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.