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Featured Holiday Homes in Cambridge

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach
Located in Owings, this vacation home is a 3-minute drive from Bayside History Museum and 6 minutes from Chesapeake Beach Water Park.
The Cozy Crab- Your Charming Haven in Lovely North Beach!
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$788 per night from 1 Sept to 2 Sept
AU$788
1 Sept - 2 Sept
includes taxes & fees
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
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton
With a stay at this vacation home in Easton, you'll be on the beach, and 6.8 mi (10.9 km) from Historical Society of Talbot County and 6.9 mi (11 km) from Easton ...
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
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Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

St. Michaels
When you stay at this vacation home in St. Michaels, you'll be on the waterfront, within a 5-minute drive of Perry Cabin Park and Saint Michaels Town Hall.
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Rising Sun Bay View Cottage

Rising Sun Bay View Cottage

Chesapeake Beach
Located in Chesapeake Beach, this vacation home is on the waterfront, a 1-minute drive from Bruce Gabrielson's Surf Art Gallery and Museum and 6 minutes from ...
Rising Sun Bay View Cottage
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
The price is AU$473 per night from 11 Aug to 12 Aug
AU$473
11 Aug - 12 Aug
includes taxes & fees
Located in Stevensville, this vacation home is within a 15-minute drive of Romancoke Wharf County Park and Matapeake State Park.
Relax on Kent Island in 3 Bedroom Home w/Waterview
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 12 minutes by car from Spocott Windmill.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
St. Michaels Waterfront Home

St. Michaels Waterfront Home

New comb
Located in Easton, this vacation home is on the waterfront, a 4-minute drive from Saint Michaels Village and 5 minutes from St. Michaels Winery.
St. Michaels Waterfront Home
The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach
Located in North Beach, this vacation home is by the sea, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
The Blue Crab Beach House - Free beach passes
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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
399 Holiday Homes
Lowest Price
AU$130
Highest Price
AU$788
Popular accommodation
The Cozy Crab- Your Charming Haven in Lovely North Beach!, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks, Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Rising Sun Bay View Cottage, Relax on Kent Island in 3 Bedroom Home w/Waterview, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, St. Michaels Waterfront Home, The Blue Crab Beach House - Free beach passes

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$437 per night from 25 Aug to 26 Aug
AU$437
25 Aug - 26 Aug
includes taxes & fees
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Meredith House.
Hyatt Regency Chesapeake Bay
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$203 per night from 3 Sept to 4 Sept
AU$203
3 Sept - 4 Sept
includes taxes & fees
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
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$130 per night from 10 Aug to 11 Aug
AU$130
10 Aug - 11 Aug
includes taxes & fees
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 Meredith ...
Days Inn & Suites by Wyndham Cambridge
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Cambridge Inn

Cambridge Inn

2 out of 5
2831 Ocean Gateway, Cambridge, MD
Fully refundableReserve now, pay when you stay
A stay at Cambridge Inn places you in the heart of Cambridge, within a 5-minute drive of Bay Country Shop and Meredith House.
Cambridge Inn
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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.