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Featured Holiday Homes in Cambridge

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Deale
With a stay at this vacation home, you'll be centrally located in Deale, within a 10-minute drive of Upper Yough River and Franklin Point State Park.
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
The price is AU$609 per night from 16 Dec to 17 Dec
AU$609
includes taxes & fees
16 Dec - 17 Dec
A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Bay views with kayaks, bikes, fire pit, crabbing and more

Bay views with kayaks, bikes, fire pit, crabbing and more

Shady Side
With a stay at this vacation home in Shady Side, you'll be within a 5-minute drive of Shadyside Park and Captain Avery Museum.
Bay views with kayaks, bikes, fire pit, crabbing and more
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Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2 out of 5
Cambridge
Located in Cambridge, this vacation home is within a 15-minute walk of Harriet Tubman Museum and Educational Center and Richardson Maritime Museum.
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Waterfront Home on the Chesapeake Bay!

Waterfront Home on the Chesapeake Bay!

Shady Side
When you stay at this vacation home in Shady Side, you'll be on the waterfront, within a 5-minute drive of Shadyside Park and Captain Avery Museum.
Waterfront Home on the Chesapeake Bay!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of St. Michaels Museum and Chesapeake Bay Maritime Museum.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Cambridge
The price is AU$793 per night from 5 Dec to 6 Dec
AU$793
includes taxes & fees
5 Dec - 6 Dec
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 8 minutes by car from Spocott Windmill.
Beautiful Waterfront Retreat in Cambridge!
Walk to Everything House

Walk to Everything House

Saint Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Walk to Everything House
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
When you stay at this vacation home in Sherwood, you'll be on the waterfront and 7 minutes by car from Tilghman Watermen’s Museum.
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
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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.

Cambridge Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cambridge vacation homes are the perfect way for you to wing it.

Holiday houses in Cambridge let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cambridge in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cambridge adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cambridge with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cambridge vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Cambridge Holiday Homes essential information

Accommodation
303 Holiday Homes
Lowest Price
AU$102
Highest Price
AU$793
Popular accommodation
Rockhold Creek Cottage, Water Front, Vacation Home, Docks, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, Bay views with kayaks, bikes, fire pit, crabbing and more, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, Waterfront Home on the Chesapeake Bay!, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Beautiful Waterfront Retreat in Cambridge!, Walk to Everything House, Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Top trending hotels in Cambridge

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is AU$368 per night from 3 Dec to 4 Dec
AU$368
includes taxes & fees
3 Dec - 4 Dec
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 6 minutes from Dorchester County Visitors ...
Hyatt Regency Chesapeake Bay
Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5
2917 Ocean Gateway, Rt.50 East, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is AU$102 per night from 24 Nov to 25 Nov
AU$102
includes taxes & fees
24 Nov - 25 Nov
When you stay at Days Inn & Suites by Wyndham Cambridge in Cambridge, you'll be near the beach, within a 5-minute drive of Bay Country Shop and Dorchester County ...
Days Inn & Suites by Wyndham Cambridge
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 out of 5
2936 Ocean Gtwy, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is AU$162 per night from 5 Dec to 6 Dec
AU$162
includes taxes & fees
5 Dec - 6 Dec
Located in Cambridge, Comfort Inn & Suites Cambridge is a 4-minute drive from Harriet Tubman Museum and Educational Center and 6 minutes from Choptank River ...
Comfort Inn & Suites Cambridge
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Holiday Inn Express Cambridge, an IHG Hotel

Holiday Inn Express Cambridge, an IHG Hotel

2.5 out of 5
2715 Ocean Gtwy, Cambridge, MD
Fully refundable
The price is AU$198 per night from 26 Nov to 27 Nov
AU$198
includes taxes & fees
26 Nov - 27 Nov
Located in Cambridge, Holiday Inn Express Cambridge, an IHG Hotel is in the business district, a 2-minute walk from Bay Country Shop and within a 5-minute drive ...
Holiday Inn Express Cambridge, an IHG Hotel
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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.

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^Subject to availability and chosen travel dates.