Downtown Cambridge Vacation Packages for 2026

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Top Hotel Deals

St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
24.98 km from Downtown Cambridge
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
2.56 km from Downtown Cambridge
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
27.68 km from Downtown Cambridge
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
22.88 km from Downtown Cambridge
Book a stay at this spa hotel in Easton. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions ...
Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5
2917 Ocean Gateway Cambridge MD
3.63 km from Downtown Cambridge
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. ...
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
27.55 km from Downtown Cambridge
Stay at this hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

2.5 out of 5
8708 Alicia Drive Easton MD
24.45 km from Downtown Cambridge
Book a stay at this business-friendly hotel in Easton. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff ...
Quality Inn

Quality Inn

2.5 out of 5
8523 Ocean Gtwy Easton MD
23.88 km from Downtown Cambridge
Book a stay at this business-friendly hotel in Easton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG

3 out of 5
8561 Ocean Gateway Route 50 Easton MD
23.99 km from Downtown Cambridge
Book a stay at this business-friendly hotel in Easton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
Cambridge Inn

Cambridge Inn

2 out of 5
2831 Ocean Gateway Cambridge MD
3.09 km from Downtown Cambridge
Stay at this hotel in Cambridge. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Bay Country Shop and Dorchester County Historical ...
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 out of 5
2936 Ocean Gtwy Cambridge MD
3.97 km from Downtown Cambridge
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Tilghman Island Inn

The Tilghman Island Inn

3.5 out of 5
21384 Coopertown Rd Tilghman MD
28.23 km from Downtown Cambridge
Stay at this guesthouse in Tilghman. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Sandaway Suites & Beach

Sandaway Suites & Beach

3 out of 5
103 West Strand Road Oxford MD
16.21 km from Downtown Cambridge
Book a stay at this beach hotel in Oxford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our reviews. Popular ...
Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton

3 out of 5
8945 Sunflower Drive Easton MD
25.52 km from Downtown Cambridge
Book a stay at this business-friendly hotel in Easton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Holiday Inn Express Cambridge by IHG

Holiday Inn Express Cambridge by IHG

2.5 out of 5
2715 Ocean Gtwy Cambridge MD
2.11 km from Downtown Cambridge
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Oct 3 - Sat, Oct 10
BOS
Logan Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$420 Roundtrip, found 3 days ago
$420
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Oct 3 from Logan Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, Oct 10, priced at $420 found 3 days ago
American Airlines
Mon, Oct 5 - Sat, Oct 10
BOS
Logan Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$450 Roundtrip, found 3 days ago
$450
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Oct 5 from Logan Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, Oct 10, priced at $450 found 3 days ago
American Airlines
Sat, Sep 26 - Tue, Sep 29
BOS
Logan Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$462 Roundtrip, found 3 days ago
$462
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Sep 26 from Logan Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, Sep 29, priced at $462 found 3 days ago
Breeze Airways
Sun, Oct 4 - Fri, Oct 9
PSM
Portsmouth Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$639 Roundtrip, found 5 days ago
$639
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, Oct 4 from Portsmouth Intl. to Salisbury - Ocean City Wicomico Regional, returning Fri, Oct 9, priced at $639 found 5 days ago