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House vacation rentals in Saint Michaels

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Top-rated house rentals in Saint Michaels

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Home in Montross

4.89 out of 5 average rating, 224 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

Our 3 bed/2 full bath+loft house sits in the woods surrounding a beautiful freshwater lake in a neighborhood on the stunning Potomac River! Come enjoy the nearby attractions or simply do nothing at all! We have kayaks/boats for your use right off the private dock. The community has 3 beaches: a private sandy lake beach with a swimming dock, a river-front sandy beach with 15 million old+ shark teeth, and a fossil cliff beach. Fishing! Seasonal hot tub on patio! Bald eagle sightings! Theater Room!

Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

"Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take a kayak out after breakfast to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acre in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home (w. 1GB hi-speed internet).

Home in Mechanicsville

4.92 out of 5 average rating, 12 reviews

Modern luxury waterfront - Fall retreat

Expansive river views from every room and on your bed! A luxurious waterfront retreat. Relax in a full marble tiled, oversized rainfall shower, rich cotton sheets and pillowtop bed. Full kitchen with Nespresso and tea. Cul-de-sac house, on a cliff with private deck/dock. High ceilings and massive windows let in lots of light. Easy access to dining, wineries, farms, beaches, and historic sites. DC/VA easy 1 hr drive away. *Host lives in adjoining building, attached guest house is fully private.

Home in Deale

4.96 out of 5 average rating, 24 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Home in St Michaels

4.85 out of 5 average rating, 118 reviews

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

Home in Newburg

4.9 out of 5 average rating, 111 reviews

The River House, a Wicomico Beach Retreat

Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The acre+ plot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos, plus a fabulous sleeping loft for the kids!

Home in Cambridge

4.98 out of 5 average rating, 121 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Come relax at our casual, pristine waterfront home. We offer 4 bedrooms w/7 beds for 10 guests. We are nestled in a small neighborhood on the beautiful Choptank River. We provide bikes, kayaks, paddleboards & yard games. Just want to relax? Enjoy hanging in the hammock or kick back on the waterfront w/a private pier. Try fishing off the pier or simply chill on the back deck or patio. At night hang out by the firepit. Explore downtown Cambridge - it's a short walk/bike ride to town.

Home in Cambridge

4.94 out of 5 average rating, 119 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Home in Montross

4.94 out of 5 average rating, 189 reviews

The Glebe

This 3br 2ba home with own private beach is nestled off of the Potomac River and boasts serene and expansive views. Sunbathe on the private beach, cool off in the water, go fishing/crabbing from the dock, or just listen to the waves crash. Whatever it is, you’ll find it absolutely relaxing. Be sure to explore local wineries, breweries, shops and enjoy the community pool and tennis court. It's the perfect getaway house for couples/families or anyone looking for a serene weekend.

Home in Scotland

4.91 out of 5 average rating, 124 reviews

Spacious Gorgeous Waterfront Home with Sunset View

Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.

Home in Annapolis

4.92 out of 5 average rating, 106 reviews

Historic Downtown House with Off Street Parking

Spacious living with all the modern amenities. Prime location - 1 block from the water, restaurants, and shops. Park your car off street (up to 3 cars) and you won't need it again! Gourmet kitchen fully stocked and ready for entertaining, enjoy the outdoor space. The whole group will enjoy easy access to everything from this centrally located place.

Home in Annapolis

4.73 out of 5 average rating, 121 reviews

Navy Stadium West Annapolis/Boat Show Gem!

Welcome! We are eager to continue providing our quests with an upgraded experience. This is a one story house! Best of AirBnb! Perfect location close to art and culture, the city center, and parks. Great house for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). One block from Navy Marine Corps Stadium!

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Popular amenities for Saint Michaels house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Edgewater

4.92 out of 5 average rating, 138 reviews

House in Edgewater Maryland

Home in Queenstown

4.81 out of 5 average rating, 155 reviews

Bay Breeze Retreat

Home in Cambridge

4.96 out of 5 average rating, 111 reviews

Waterfront, Fabulous Home for Families with Pool!

Home in Severn

4.86 out of 5 average rating, 138 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

Home in Montross

4.99 out of 5 average rating, 143 reviews

Beach Please! River cottage w/private beach & dock

Home in Tracys Landing

4.99 out of 5 average rating, 195 reviews

The Little Gypsy BoHome

Home in Stevensville

5 out of 5 average rating, 124 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Home in Lusby

5 out of 5 average rating, 133 reviews

Historic Rousby Hall, Waterfront, Patuxent River

Weekly house rentals

Home in Washington Village - Pigtown

4.73 out of 5 average rating, 22 reviews

Townhouse 3 Bedrooms/2 Baths/ Gated Free Parking

Home in Wye Mills

4.91 out of 5 average rating, 11 reviews

⇚Family Getaway⇛| Lakeside + A Nature View |

Home in Shady Side

5 out of 5 average rating, 143 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Home in Cambridge

4.95 out of 5 average rating, 223 reviews

Great Historic Cambridge Home With Parking!

Home in Dameron

5 out of 5 average rating, 33 reviews

Dameron Farm on the Water - Private Pool

Home in College Park

4.82 out of 5 average rating, 168 reviews

Spacious relaxing home by DC, CP, woods & lake

Home in Deale

4.98 out of 5 average rating, 103 reviews

140ft Dock, Pet-Friendly 8 Acre Waterfront Oasis !

Home in Suitland

5 out of 5 average rating, 8 reviews

Spacious 7BR/5BA Retreat: Perfect for Large Groups

Private house rentals

Home in North Beach

5 out of 5 average rating, 14 reviews

Stunning North Beach Getaway w/ Inground Pool

Home in Riva

4.87 out of 5 average rating, 46 reviews

Riverfront Retreat 7mil from MD Renaissance Fest!

Home in Stevensville

4.94 out of 5 average rating, 242 reviews

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Home in Rock Hall

4.94 out of 5 average rating, 35 reviews

Rockfish Keeper

Home in Edgewater

4.98 out of 5 average rating, 52 reviews

Entire Beach House with Pool and Hot Tub

Home in Arnold

4.81 out of 5 average rating, 26 reviews

Entire Private 2 bedrooms house, nice neighborhood

Home in Taylors Island

4.97 out of 5 average rating, 38 reviews

A Vacation for All, Away From It All

Home in Centreville

4.63 out of 5 average rating, 92 reviews

Peaceful Acres Guest House (A Nature's Getaway)

Quick stats about house rentals in Saint Michaels

Total rentals
20 properties
Nightly prices starting at
$180 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Wifi availability
20 properties include access to wifi

Destinations to explore