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Cambridge Rentals

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35 Results

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35 Houses

Cambridge Colonial Home, Walk to Town & Waterfront

Cambridge house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 26 minutes

Price per night from

$235

6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

Cambridge house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,028

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 clean and well furnished. The dining room table and table on the porch provided plenty of seating for meals. There was plenty of hot water for showers and clean-up after meals. The pool was clean and the river was awesome, with a gradual slope that was perfect for kids and adults. We used the crab traps provided and caught 2 dozen crabs that made a great contribution to dinner on Friday. Crabbing was best by the dock. We caught all but 3 crabs there, rather than out closer to the middle of the river. The AC on the ground floor stopped working on Tuesday, but one call to the owner and the repair team was on-site in less than 2 hours. The issue was resolved before noon on Wednesday. We have been renting vacation properties for years and issues crop up from time to time. We appreciated the quick response and resolution. The one recommendation we will make is to bring bug spray (mosquitos and horse flies). We anticipated it being right on the river, but if you haven't had that experience, you need to be prepared.

Price per night from

$707

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 propabaly the most memorable week our family has ever spent together. The house was absolutely perfect! Clean, beautifully furnished, amenities for all ages and the most spectacular grounds and views for the entire family to enjoy. We are already planning our stay for next summer and hope to come back this winter as well for a long weekend. Thank you thank you thank you!

Price per night from

$1,656

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Cambridge cottage

3 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 34 minutes

Price per night from

$186

Great rentals within 20 miles that match your search

Waterfront Room Rentals 1 with Private Beach

Trappe private room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 54 minutes

Price per night from

$154

Waterfront Vacation Home with Private Beach

Trappe house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 54 minutes

Price per night from

$390

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$456

Historic Waterfront Property with Wi-Fi and Dock

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 14 minutes

Price per night from

$887

Deerpond Carriage House

Woolford guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$213

RESTORED WATERFRONT COTTAGE

Royal Oak cottage

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$586

St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$590

EASTERN SHORE MARYLAND WELCOMES YOU

Preston house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 54 minutes

Price per night from

$89

Waterfront Room Rentals 3 with Private Beach

Trappe private room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 54 minutes

Price per night from

$119

Waterfront Room Rentals 2 with Private Beach

Trappe private room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 54 minutes

Price per night from

$119

Maryland’s Eastern Shore Welcomes You

Preston house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 54 minutes

Price per night from

$103

Best kept secret by the bay (Entire House)

Fishing Creek house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$200

NEW! Quiet Sailor’s Home with Pier and Bay Vistas!

Tilghman house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Price per night from

$278

Chesapeake Bay Waterfront on Hoopers Island with Private Beach

Fishing Creek house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 54 minutes

Price per night from

$284

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

“5 out of 5” I spent a long weekend at the main house, and it was easily the best weekend of the summer! The location is phenomenal. The house sits on large stretch of beautiful waterfront property. The views from the piers and the pool are exquisite. As for the house itself, we couldn't have asked for more. It is spacious, clean, and has all of the amenities you could want. I must also mention that it was a breeze and a pleasure working with the folks at Grandview. They are incredibly responsive, and make a great effort to ensure that you enjoy your stay.

Price per night from

$789

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$442

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$280

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$280

Eastern Shore Waterfront Home, Ready for Spring and Summer!

Fishing Creek house

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$343

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 42 minutes

Price per night from

$400

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 40 minutes

Price per night from

$176

Hoopers Island Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge

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 more. The décor was adorable, though both aesthetically and functionally vintage. We found a very thoughtful welcome bag and bottle of wine on the dining table as soon as we walked in. A variety of items found throughout the house make for a very comfortable and carefree stay (including a blender, coffee maker, coffee, a wide variety of DVD/VHS movies, and more). The kitchen was fully stocked with all of the essentials, as well as a great assortment of spices. It truly feels like your home away from home. Fishing Creek is a modest town, but houses some of the friendliest people. There is only one general store and one restaurant – both terrific. We arrived at the general store five minutes after closing and they still opened the doors for us. The restaurant, Old Salty’s, has fast, friendly, and accommodating service and the food is very good. Not to mention, the largest and cleanest oysters we have ever tried. We spent much of our time relaxing and enjoying the amenities that the Haven provides. The screened porch makes for a wonderful place to have an outdoor dinner. The fire pit in the back kept us warm as we took in some of the most beautiful sunsets we have ever seen. We even caught a few crabs just off the dock up front, using the crab traps that Debi provided. Unfortunately, we found no luck with catching any fish. Debi was out of town during our stay, yet she still provided wonderful service. Her responses to text messages and e-mails were always very prompt. She left the Haven very tidy for us, and included a detailed instruction manual that covered scenario we may have come across. It’s obvious she puts a lot of thought into giving her guests a pleasant stay, and it surely pays off. We really enjoyed our time at the Haven, and have already talked about a possible return trip in the future. Thanks Debi!

Responds fast! avg. 1 hour 5 minutes

Price per night from

$184

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Responds fast! avg. 3 hours 49 minutes

Price per night from

$247

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$229

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 49 minutes

Price per night from

$235

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 you could ever need and is very unique and quaint. The location is more than perfect (we literally were in walking distance of everything, shops, restaurants, etc.) and did not even have to get into the car to drive anywhere the entire time. The backyard has a wonderful porch where you can sit outside and converse with friends or even sip your coffee in the morning. The view is phenomenal! You have a wonderful panoramic view of the water from your bedroom window and the beds are very comfortable (which is a must for me). If you are planning on a trip to experience St. Michael's whether it is a romantic weekend getaway or a family (group) outing I would hands down recommend this house.

Responds fast! avg. 3 hours 49 minutes

Price per night from

$447

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 building has been lovingly restored keeping to the historical accuracy, yet well placed modern conveniences make the stay even more enjoyable. I have visited this cottage several times and will continue to do so! A great place to gather with family and friends or a quick weekend escape to enjoy life on the shore.

Responds fast! avg. 3 hours 49 minutes

Price per night from

$281

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$6,870

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

St. Michaels house

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$205

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 49 minutes

Price per night from

$247

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Top Destination reviews

Year Round Estate on Bay / Fam. Reunions / Slps 28
An amazing and beautiful wedding experience

I had my wedding at this property. The landlord, Frank, was very polite and easy going. He allowed for our dogs to stay for a low fee and was very good at returning calls. The house was breathtakingly gorgeous. As our families joined us, they also felt the house was amazing and hope to rent here again. People still talk about how beautiful the wedding was. We had the ceremony and reception right there behind the house on the bay. The pictures turned out beautiful especially when the sun was setting. The wedding consisted of 54 people, but there was room for more. All guest were able to stay at hotels which were about 15 minutes away. At the end of the evening, some guest swam, some enjoyed the sunset on the dock, and others danced their feet off. I don't think our wedding would have been nearly as wonderful, if we had not had it at Captain's Quarters!see more
Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths
Wonderful family vacation!

This was a perfect setting for our family vacation. Our grandkids ages range from 4-17 and they all enjoyed biking, kayaking, swimming, fishing and playing in the sand. The house was beautiful and the surroundings were lovely. We all enjoyed this magical vacation!!! … see more

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