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Cambridge Rentals

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Cambridge Rentals

40 Houses

NEW! Colonial Home in Cambridge w/Wraparound Porch

Cambridge house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 12 minutes

Price per night from

$220

1 / 29

Choptank River View House

Cambridge house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$993

1 / 16

6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

Cambridge house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$863

1 / 8

Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths

Cambridge house

6 bedrooms / 5 bathrooms / sleeps 20

“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was cle

Responds fast! avg. 3 hours 27 minutes

Price per night from

$493

1 / 31

Year Round Estate on Bay / Fam. Reunions / Slps 28

Cambridge house

7 bedrooms / 7 bathrooms / sleeps 28

“Unbelievable Home in an Unbelievable Setting!!!” Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand parents, etc) and it was prop

Price per night from

$1,000

1 / 35

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Cambridge cottage

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$166

1 / 50

Great rentals within 20 miles that match your search

Waterfront Room Rentals 1 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 34 minutes

Price per night from

$130

1 / 34

Waterfront Vacation Home with Private Beach

Trappe house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 34 minutes

Price per night from

$326

1 / 55

Best kept secret by the bay (Entire House)

Fishing Creek house

3 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 33 minutes

Price per night from

$168

1 / 20

Waterfront Room Rentals 2 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 34 minutes

Price per night from

$100

1 / 42

Waterfront Room Rentals 3 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 34 minutes

Price per night from

$100

1 / 44

St. Michaels Waterfront Home W/Dock for 2 boats

Neavitt house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$224

1 / 18

St. Michaels Area Waterfront Retreat with pier, pool, kayaks and bikes

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$599

1 / 4

Chesapeake Bay Waterfront on Hoopers Island with Private Beach

Fishing Creek house

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$295

1 / 33

Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

Tilghman cottage

3 bedrooms / 2 bathrooms / sleeps 6

“We loved it!” We had a great (albeit too short!) family getaway at the Roost! The cottage is extremely clean, comfortable, well-maintained, and spacious. The kids (ages 6 and 20 months) loved it -- especially the bunk beds and the nice backyard, and t

Price per night from

$199

1 / 20

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 32 minutes

Price per night from

$160

1 / 23

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that

Responds fast! avg. 3 hours 32 minutes

Price per night from

$290

1 / 30

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

“Crabtastic Great Escape” This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The buildin

Responds fast! avg. 3 hours 32 minutes

Price per night from

$148

1 / 27

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 12 minutes

Price per night from

$174

1 / 28

Best sunrise in St. Michaels....Broadview Bay House

St. Michaels house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$596

1 / 24

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$244

1 / 8

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 32 minutes

Price per night from

$150

1 / 24

Historic Waterfront Property with Wi-Fi and Dock

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$745

1 / 18

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Responds fast! avg. 3 hours 32 minutes

Price per night from

$160

1 / 25

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$383

1 / 9

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$596

1 / 15

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$373

1 / 22

Hoopers Island Studio, 360 Degrees WATER VIEWS

Fishing Creek apartment

1 bedroom / 1 bathroom / sleeps 3

“What a fantastic stay!” As soon as we stepped out of our car, we felt like we hit the jackpot. The views in front and in back of the house are breathtaking, with water stretching to the horizons. Inside the house, we found all that we could need and

Responds fast! avg. 1 hour 35 minutes

Price per night from

$155

1 / 38

Harris Cove Cottages LLC

St. Michaels cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$199

1 / 12

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$245

1 / 6

Eastern Shore Waterfront Home, Ready for Spring and Summer!

Fishing Creek house

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$222

1 / 9

Halo's Haven Guest Quarters

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$325

1 / 14

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$283

1 / 7

Deerpond Carriage House

Woolford guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$180

1 / 17

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

St. Michaels villa

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 1 hour 1 minutes

Price per night from

$839

1 / 38

RESTORED WATERFRONT COTTAGE

Royal Oak cottage

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$300

1 / 24

Maryland’s Eastern Shore Welcomes You

Preston house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$87

1 / 20

EASTERN SHORE MARYLAND WELCOMES YOU

Preston house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$74

1 / 23
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