House vacation rentals in St. Michaels

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Top-rated house rentals in St. Michaels

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Top guest favorite

A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.

Home in North Beach

5 out of 5 average rating, 155 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

Top guest favorite

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

4.95 out of 5 average rating, 281 reviews

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

Top guest favorite

The exterior of the cottage is framed by vibrant flowerbeds filled with blooming roses and lush green shrubs. A well-manicured path leads to the entrance, flanked by tall greenery, with glimpses of the sparkling water visible in the background.

Home in Shady Side

5 out of 5 average rating, 184 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

Top guest favorite

A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.

Home in Cambridge

4.99 out of 5 average rating, 181 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Top guest favorite

The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.

Home in Lusby

5 out of 5 average rating, 155 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

**Heated pool open to Nov 2. Thanksgiving chef dinner options** Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee additional).

Guest favorite

A spacious bedroom features a large wooden bed with a light comforter and decorative pillows. Two leather benches are positioned at the foot of the bed. Natural light fills the room through large windows adorned with wooden shades, and a ceiling fan adds to the comfort.

Home in Montross

4.98 out of 5 average rating, 117 reviews

3N+ Promo| Waterfront | Beach+Gamerm+Kayak+Firepit

*Ask about our 3+ Night promotions* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨‍🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK 🎯 Gameroom ⚡️EV Outlet If you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! Book your getaway today or ❤️ us for next time!

Top guest favorite

The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.

Home in Solomons

5 out of 5 average rating, 107 reviews

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Top guest favorite

A bright sun porch features a round glass dining table surrounded by four light-colored chairs. Large windows provide views of the waterfront, allowing natural light to fill the space. A cozy seating area is visible in the background, offering a serene atmosphere.

Home in Leonardtown

5 out of 5 average rating, 135 reviews

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

Top guest favorite

A charming two-story cottage features a light green exterior with white trim. The welcoming front porch is furnished with two white chairs and a small table, while a bright red door serves as the main entrance. A private balcony is visible above, framed by railing.

Home in Saint Michaels

4.99 out of 5 average rating, 123 reviews

Shipwrights Cottage in Town!

Charming historic cottage within walking distance to all St. Michaels has to offer! Relax & enjoy the sights of town from your front porch! Once a working shipwrights cottage, this home is 2 stories with a 1st floor full kitchen, combo living-dining room, den with queensize pullout couch & full bath. The 2nd floor has 2 bedrooms & a full bath. Both bedrooms have vaulted ceilings & ceiling fans. The primary bedroom has a private sitting balcony. Walk to shops, restaurants & waterfront!

Guest favorite

The exterior of the farmhouse showcases a large, white structure with multiple windows and a spacious lawn surrounded by trees. The scene is complemented by a clear sky, creating a serene environment. Outdoor seating appears to be arranged on the patio, inviting relaxation.

Home in Chester

4.94 out of 5 average rating, 105 reviews

Waterfront Farmhouse Meets Modern Luxury

Enjoy all that the Eastern Shore has to offer while staying at the neoclassical 19th-century "Osprey's Reach" farmhouse. Osprey's Reach blends the original character of Kent Island with modern comforts of a full house restoration, all while enjoying stunning sunsets over the Chesapeake, from the private dock or poolside. Kent Island is centrally located for short day trips to Annapolis, Easton, St. Michael's or Chestertown, with family-friendly dining and shopping options on-island.

Top guest favorite

A charming blue cottage is depicted with a gabled roof and white columns framing the entrance. Lush green bushes line the pathway, providing an inviting approach. Clear blue skies and tall trees are visible in the background, enhancing the peaceful setting.

Home in Saint Michaels

4.98 out of 5 average rating, 109 reviews

SM’s Premier Rental Heated Pool (closes 10/28)

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

Top guest favorite

The cottage features a charming white exterior with blue shutters, sitting gracefully adjacent to a tree-lined street. A welcoming front porch is adorned with two white chairs, while a neat white picket fence outlines the inviting garden space.

Home in Saint Michaels

4.99 out of 5 average rating, 182 reviews

Grace Cottage, Saint Michaels Walk to everything!

Welcome to Grace Street Cottage with a newly renovated kitchen! Located in the heart of Saint Michaels. Walk to shops, restaurants and experience the best of the Eastern Shore. This cottage has all you will need for a perfect getaway. Sit by the fire pit and grill out or take a few steps to Talbot Street where your dining options are endless! Pack your bags and head to the shore! The experience awaits you!