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Compare 74 Cottages in Cambridge with updated reviews, rates, and availability.

Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Soul Oasis - home on the Chesapeake Bay
Exterior

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (17)
"Beautiful and quiet in the fall. A great place for relaxing. Clean, great communication. End of the street with views of the bay. "
The price is SAR 563
SAR 1,166 total
includes taxes & fees
1 Dec - 2 Dec
Soul Oasis - home on the Chesapeake Bay
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Front and side view of Blades House from Locust St.

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (134)
"We loved this house, it was perfect for exploring town and as a base for things further afield. Comfortable, thoughtfully and well stocked with lots of charm."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Eastern Shore Waterside Cottage Near St. Michaels
wrap around porch with rockers and dining area

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Blue heron sunset

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (7)
"“Point of View” waterfront cottage did not disappoint. In fact, it was beyond expectations. Maria’s (the host) personal touches made the cottage feel like home. We used “Point of View” as overflow for a family reunion we were having. It is perfectly situated for easy walking to anything you need or want to do on Tilghman Island. The views from the cottage are amazing. Being on the entrance to Dogwood Harbor provides you with a real time experience of what a waterman’s life is truly all...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Deal Island Bay Cottage
Sunsets at the nearby beach

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is SAR 432
SAR 816 total
includes taxes & fees
2 Dec - 3 Dec
Deal Island Bay Cottage
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Front of Carpenter St. Cottage

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (168)
"We went to St. Michael’s for a wedding. The cottage was great. Very charming. The location was perfect. We could walk everywhere. We had great communication with the host. He was very accommodating. We will stay there again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Updated North Beach Cottage: Pet Friendly!
North Beach Vacation Rental | 3BR | 2BA | 1,440 Sq Ft | Stairs Required to Enter

Updated North Beach Cottage: Pet Friendly!

10.0 out of 10, Exceptional, (11)
"Adorable cottage with updated amenities. A great retreat for friends or a family!! "
Updated North Beach Cottage: Pet Friendly!
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
Every sunrise brings new hope for a brighter future.

Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

10.0 out of 10, Exceptional, (46)
"Great experience, wonderful cozy cottage with thoughtful touches throughout. Remote, peaceful location with excellent fishing and crabbing all around you. Fantastic eating at Old Salty's less than a couple of miles away. Very dog friendly cottage and lovely screened in porch area to sit and watch the sunsets. We will be booking again next year."
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
Cozy Cottage with access to and partially obstructed views of the bay.
Exterior

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (13)
"Away from the hustle and bustle of any city but close enough to get anything you need. Our stay was very relaxing and Hyrum and Lisa were the best hosts we have had so far... Will definitely look for them again if we are in the area again..."
Cozy Cottage with access to and partially obstructed views of the bay.
Cottage at Goose Neck Point
Living area

Cottage at Goose Neck Point

10.0 out of 10, Exceptional, (31)
"We loved everything about this sweet cottage on the water! The decor was top notch, and so welcoming! We stayed 3 nights, and can’t say enough about this beautiful area of Maryland. Great restaurants, shoppes, and delicious crabs! We also did the ferry ride over to Oxford. Had an amazing time at this property! The host also left some yummy treats, and a bottle of champagne for our anniversary! Can’t wait to come back!"
Cottage at Goose Neck Point
Perfect family / friend getaway. Kayaks and bikes provided. Walk to Herrington H
Inviting cottage beside wooded lot for privacy.

Perfect family / friend getaway. Kayaks and bikes provided. Walk to Herrington H

9.6 out of 10, Exceptional, (90)
"Great location for a wedding stay. Beautiful home, professionally managed!"
Perfect family / friend getaway. Kayaks and bikes provided. Walk to Herrington H
Waterfront Cottage in Beautiful Hoopers Island
Enjoy a beautiful sunrise from the back deck

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (63)
"My boyfriend and I needed to get away. This house and location was just what we needed. Beautiful scenery, cozy home. We started a full week and I was sad to go at the end of our trip. We look forward to visiting again in the future! "
Waterfront Cottage in Beautiful Hoopers Island
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Front and side of W Melson House

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (115)
"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Front of house from St. Michaels harbor looking across Town Park

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (112)
"Our stay in St Michael's was wonderful. The location of this property could not be better. Close to marina, parks, restaurants, historic downtown and the maritime museum. We never needed to use our car! Tom is an excellent host. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
The Middle Point Cabin in Saint Michaels
Living area

The Middle Point Cabin in Saint Michaels

9.8 out of 10, Exceptional, (48)
"nice property. secluded. clean and comfortable. owners very very responsive. "
The Middle Point Cabin in Saint Michaels
Waterfront, cozy cottage with private pool on 27 acres
Private Pool

Waterfront, cozy cottage with private pool on 27 acres

9.8 out of 10, Exceptional, (87)
"We had a wonderful time overlooking the water and swimming in the refreshing pool while enjoying easy access to downtown Cambridge and Blackwater NW Refuge."
Waterfront, cozy cottage with private pool on 27 acres
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"Beautiful, tranquil setting. Hostess was very accommodating. Access to all of the right elements: kayaks, fire pitfire, plenty of outdoor seating, tiki torches, gas grill and more. "
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (2)
"Great little cottage, beautiful scenery, quiet and peaceful. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Waterfront property with private boat ramp and new dock!
Exterior

Waterfront property with private boat ramp and new dock!

9.6 out of 10, Exceptional, (8)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!
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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Other property types in Cambridge

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Cambridge Vacation Rental | 7BR | 5.5BA | Stairs Required | 10,333 Sq Ft

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (17)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Beautiful Waterfront Retreat in Cambridge!
Exterior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (31)
"This house exceeded our expectations in every way. The kitchen is large and well-appointed, the beds are comfortable, and the peace and quiet is priceless. We enjoyed morning coffee in the sunroom, table tennis in the crab house, sunsets from the dock, and stargazing at the firepit. If you desire peace and quiet this house is a perfect choice!"
The price is SAR 1,032
SAR 1,926 total
includes taxes & fees
1 Dec - 2 Dec
Beautiful Waterfront Retreat in Cambridge!
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
Aerial property view

Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach

9.8 out of 10, Exceptional, (55)
"The original home is unique and gorgeous and the additions, the sunroom facing sunrises and the lodge style master chef kitchen gave us plenty of room to spread out. The large lawn and driveway gave us plenty of areas to walk the dogs and the beach was a daily swim spot for the dogs. The pool was one of the nicest we have had yet. We love the places with nice pools facing the boats out on the water. We will be back again for sure"
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
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.

Frequently asked questions

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