Holiday houses in Saint Michaels

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Top-rated holiday rentals in Saint Michaels

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Guest favourite

Cottage in Saint Michaels

4.98 out of 5 average rating, 423 reviews

St. Michaels-Historic Dist. Margaret Wells House

The Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.

1–8 Mar

$399 NZD per night

Guest favourite

Apartment in Saint Michaels

4.91 out of 5 average rating, 124 reviews

Charming Studio in the heart of St. Michael's, MD.

Welcome to Lucky Ducks Studio! Enjoy a fully renovated furnished studio in the heart of St. Michael's, MD. Located on Talbot Street in the historic 1850’s McMillian House, the 2nd floor studio offers couples a cozy "British" style experience that sleeps 4 (queen size bed & sofa that transitions to queen), a full bath with a claw tub and a gorgeous industrial style kitchen. Your steps away from the Miles River, shopping, museums, restaurants, breweries and wineries. Free WIFI and YouTube TV.

18–25 Jul

$738 NZD per night

Guest favourite

Farm stay in Madison

4.98 out of 5 average rating, 161 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

24 Feb – 3 Mar

$227 NZD per night

Guest favourite

Houseboat in Grasonville

4.99 out of 5 average rating, 115 reviews

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

11–18 Feb

$349 NZD per night

Guest favourite

Guesthouse in Easton

4.99 out of 5 average rating, 543 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.

15–20 Oct

$269 NZD per night

Guest favourite

Cottage in Saint Michaels

4.99 out of 5 average rating, 136 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

24 Sep – 1 Oct

$954 NZD per night

Guest favourite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

8–15 Dec

$230 NZD per night

Guest favourite

Guesthouse in Stevensville

5.0 out of 5 average rating, 205 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

7–14 Nov

$510 NZD per night

Guest favourite

Cottage in Saint Michaels

4.98 out of 5 average rating, 172 reviews

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

13–20 Aug

$495 NZD per night

Guest favourite

Tiny home in Cambridge

4.99 out of 5 average rating, 154 reviews

Blackwater Refuge House on The Farm, water access

The Little House on The Farm is located on a beautiful family farm in rural Dorchester County! Located just 1.5 miles from the Blackwater Wildlife Refuge and Harriet Tubman National Park, This space is quaint,yet provides all the basics for a cozy welcoming getaway! Bring your bikes and cycle to the refuge and kayak in the Blackwater River. Kitchen is fully stocked for cooking. Coffee, tea and basic condiments and all linens and towels are provided.

2–9 Aug

$200 NZD per night

Guest favourite

Guest suite in Saint Michaels

4.78 out of 5 average rating, 328 reviews

Gorgeous Cottage: Easy Walk into St Michaels Town!

Gorgeous, sunny former artist loft with great views. Across from Miles River & harbor. Walk to town! Shopping, brewery, winery, museum, restaurants await! Located in historic Bentley Hay, the lodge is perfect for relaxing walks while runners and bikers explore spectacular sights, including the nearby St Michaels Nature Trail. Or rent a kayak and explore San Domingo Creek! NO PETS OR SMOKING. 4 GUESTS MAX BY LAW. Talbot Co License STR-716-KIM

23–30 Jun

$301 NZD per night

Guest favourite

Home in Cambridge

4.92 out of 5 average rating, 178 reviews

Guest House: Farm homestead

Quiet country guest house with 1 BR/ 1 BA, queen sleeper sofa and fully stocked kitchen. Coffee/creamer/sugar provided. Come relax & enjoy the row boat and paddle boat, fishing in the ponds (C&R, No Pond Access from August 24 thru January 30 annually), grill on the deck, watch the bikers roll by (Ironman course) or finish your day by the fire-pit with s'mores! All this and only 3 miles to town and on the Eagle Man and Iron Man race course.

18–25 Aug

$230 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Saint Michaels holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Saint Michaels's top sights

Chesapeake Bay Maritime Museum39 locals recommend

Ava's Pizzeria & Wine Bar - St. Michaels20 locals recommend

The Crab Claw11 locals recommend

Foxy's Harbor Grille17 locals recommend

Sail Selina II, St. Michaels6 locals recommend

Carpenter Street Saloon10 locals recommend

Other great holiday rentals in Saint Michaels

Guest favourite

Home in Annapolis

4.96 out of 5 average rating, 106 reviews

Historic Downtown in-law suite

4–11 Feb

$242 NZD per night

Guest favourite

Loft in Lusby

5.0 out of 5 average rating, 310 reviews

Coastal Treetop Retreat w/ Private Beach Access

25 Dec – 1 Jan

$240 NZD per night

Guest favourite

Apartment in Saint Michaels

4.96 out of 5 average rating, 23 reviews

Blue Crab Lodge

8–15 Jul

$594 NZD per night

Guest favourite

Home in Saint Michaels

5.0 out of 5 average rating, 34 reviews

Shipwrights Cottage in Town!

19–26 Mar

$481 NZD per night

Guest favourite

Guesthouse in Cambridge

5.0 out of 5 average rating, 12 reviews

Camelot Cottage

30 Jan – 6 Feb

$165 NZD per night

Guest favourite

Guesthouse in Oxford

4.99 out of 5 average rating, 81 reviews

The Nichols House Cottage

29 Jul – 5 Aug

$248 NZD per night

Guest favourite

Home in Saint Michaels

4.98 out of 5 average rating, 82 reviews

SM’s Premier Rental Heated Pool opens 4/12

6–13 Oct

$1,432 NZD per night

Guest favourite

Cabin in Saint Michaels

4.99 out of 5 average rating, 96 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

26 Nov – 3 Dec

$2,122 NZD per night

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Quick stats about holiday rentals in Saint Michaels

Total rentals	40 properties
Rentals with a pool	10 properties have a pool
Pet-friendly rentals	20 properties allow pets
Family-friendly rentals	20 properties are a good fit for families
Total number of reviews	2.8K reviews
Nightly prices starting at	$186 NZD before taxes and fees

Holiday houses in Saint Michaels

Top-rated holiday rentals in Saint Michaels

Cottage in Saint Michaels

Apartment in Saint Michaels

Farm stay in Madison

Houseboat in Grasonville

Guesthouse in Easton

Cottage in Saint Michaels

Guest suite in Tilghman Island

Guesthouse in Stevensville

Cottage in Saint Michaels

Tiny home in Cambridge

Guest suite in Saint Michaels

Home in Cambridge

Holiday rentals for every style

Cottages

Houses

Hotels

Popular amenities for Saint Michaels holiday rentals

Stay near Saint Michaels's top sights

Other great holiday rentals in Saint Michaels

Home in Annapolis

Loft in Lusby

Apartment in Saint Michaels

Home in Saint Michaels

Guesthouse in Cambridge

Guesthouse in Oxford

Home in Saint Michaels

Cabin in Saint Michaels

Quick stats about holiday rentals in Saint Michaels

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

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