COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Houses St. Michaels

Updating...

age 0-16
64 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

64 houses

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 6 minutes

Match: Rental types

All filters match

Price per night from

$352

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 4 minutes

Match: Rental types

All filters match

Price per night from

$878

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Rental types

All filters match

Price per night from

$718

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

5 bedrooms / 3 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$2,340

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

6 bedrooms / 6 bathrooms / sleeps 12

Match: Rental types

All filters match

Price per night from

$2,340

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

6 bedrooms / 6 bathrooms / sleeps 12

Match: Rental types

All filters match

Price per night from

$1,890

Great rentals within 20 miles that match your search

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

Match: Rental types

All filters match

Price per night from

$498

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

Match: Rental types

All filters match

Price per night from

$462

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Match: Rental types

All filters match

Price per night from

$223

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Match: Rental types

All filters match

Price per night from

$328

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Match: Rental types

All filters match

Price per night from

$1,047

Love Point Waterfront

Kent Island house

3 bedrooms / 3 bathrooms / sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

Match: Rental types

All filters match

Price per night from

$468

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

4 bedrooms / 2 bathrooms / sleeps 12

Match: Rental types

All filters match

Price per night from

$1,989

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Rental types

All filters match

Price per night from

$1,989

Responds fast! avg. 55 minutes

Match: Rental types

All filters match

Price per night from

$468

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Match: Rental types

All filters match

Price per night from

$1,170

Breathtaking Waterfront Cambridge Getaway

Cambridge house

3 bedrooms / 2 bathrooms / sleeps 12

Match: Rental types

All filters match

Price per night from

$696

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

8 bedrooms / 10 bathrooms / sleeps 12

Match: Rental types

All filters match

Price per night from

$2,925

Golf..Fish..Hunt..Shop - A PAR for the Course & Mile to Beach on Kent Island

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 11

Match: Rental types

All filters match

Price per night from

$775

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!

Responds fast! avg. 2 hours 18 minutes

Match: Rental types

All filters match

Price per night from

$1,895

Main House at Grandview at Pleasure Point

Bozman house

4 bedrooms / 3 bathrooms / sleeps 9

“Family Fun at Grandview” Our group of grandparents, children with spouses, & grandchildren spent a week in the main house at Grandview. We had a great time in the pool, on the docks, in the porches, & exploring this very large & private property. We also enjoyed the shopping, restaurants, & Maritime Museum in St. Michaels. It was a very hot week & the many fans that were provided made it comfortable. The kitchen was well equipped to handle a large group & we had a great seafood feast on the picnic tables by the pool.

Match: Rental types

All filters match

Price per night from

$666

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 7

Match: Rental types

All filters match

Price per night from

$401

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

Match: Rental types

All filters match

Price per night from

$804

Cozy cottage with expansive backyard and firepit!

Tracys Landing house

2 bedrooms / 1 bathroom / sleeps 4

Match: Rental types

All filters match

Price per night from

$287

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$345

Indoor pool and spa located in beautiful Southern Maryland woodlands

Chesapeake Beach house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$1,109

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

Cambridge house

6 bedrooms / 5 bathrooms / sleeps 18

“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.

Responds fast! avg. 3 hours 2 minutes

Match: Rental types

All filters match

Price per night from

$918

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Edgewater house

2 bedrooms / 1 bathroom / sleeps 8

Match: Rental types

All filters match

Price per night from

$575

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 4 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$6,890

Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA

Cape Saint Claire house

2 bedrooms / 1 bathroom / sleeps 6

Match: Rental types

All filters match

Price per night from

$402

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 30 minutes

Match: Rental types

All filters match

Price per night from

$173

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Match: Rental types

All filters match

Price per night from

$801

Seize the Bay at Waterfront Kent Island home with Hot Tub (Open!)

Stevensville house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Match: Rental types

All filters match

Price per night from

$416

Take your Leave of Absence around gorgeous gardens with a private driveway

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 2 hours 25 minutes

Match: Rental types

All filters match

Price per night from

$402

PARKING and Pet Friendly Renovated Eastport Firehouse in Annapolis

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Match: Rental types

All filters match

Price per night from

$288

Steps to Main Street with View of the Capital & Parking

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Match: Rental types

All filters match

Price per night from

$386

Seashell in the City 2 parking spots and Walkable to Main Street!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Match: Rental types

All filters match

Price per night from

$195

Historic Charm! Walk from Wisteria to Waterfront & Academy with Parking

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Match: Rental types

All filters match

Price per night from

$432

Viewing 38 of 64
houses in St. Michaels

×

Also consider