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Featured Cottages in St. Leonard

Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island

Fishing Creek
Located in Fishing Creek, this cottage is on the waterfront, a 5-minute drive from P. L. Jones Marina and 6 minutes from Middle Hooper Island.
Waterfront Cottage in Beautiful Hoopers Island
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Newburg
With a stay at this cottage in Newburg, you'll be on the waterfront, and 7 mi (11.3 km) from Cooksey Island and 7.9 mi (12.7 km) from Potomac River.
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
North Beach Cottage - Walk to Chesapeake Bay

North Beach Cottage - Walk to Chesapeake Bay

North Beach
Located in North Beach, this cottage is by the sea, a 3-minute walk from Bayside History Museum and within a 5-minute drive of Chesapeake Beach Water Park.
North Beach Cottage - Walk to Chesapeake Bay
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 Artists, writers & creative minds  IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman Island
Located in Tilghman, this cottage is on the waterfront, within a 5-minute drive of Tilghman Watermen’s Museum and Talbot County Library Tilghman Branch.
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Lusby
Located in Lusby, this cottage is on the waterfront, a 5-minute drive from Drum Point Lake and 7 minutes from Seahorse Beach.
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge
With a stay at this cottage in Cambridge, you'll be on the waterfront, and 6.3 mi (10.1 km) from Ragged Island and 7.6 mi (12.2 km) from Spocott Windmill.
Family and Pet-Friendly, Waterfront with Pier
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings
With a stay at this cottage in Owings, you'll be on a river, a 3-minute walk from Fridays Creek Winery and a 4-minute drive from Patuxent River.
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict
Located in Benedict, this cottage is on the waterfront, a 1-minute drive from Patuxent River and 7 minutes from Running Hare Vineyard.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣

Fishing Creek
Located in Fishing Creek, this cottage is on the waterfront, a 2-minute drive from P. L. Jones Marina and 6 minutes from Gunners Island.
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣
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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.

St. Leonard Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in St. Leonard will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to St. Leonard definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in St. Leonard, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

St. Leonard Cottages essential information

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86 Cottages
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Popular accommodation
Waterfront Cottage in Beautiful Hoopers Island, Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing, North Beach Cottage - Walk to Chesapeake Bay, Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE, Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit, Family and Pet-Friendly, Waterfront with Pier, Relaxing, peaceful house in Calvert County, Md close to beach towns and DC., Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch., Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣

Top trending hotels in St. Leonard

New! Cozy River Cottage with great views of the water!

New! Cozy River Cottage with great views of the water!

Saint Leonard
Located in St. Leonard, this vacation home is on the waterfront, within a 15-minute drive of Perigeaux Vineyards and Winery and Jefferson Patterson Park and ...
New! Cozy River Cottage with great views of the water!
Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
With a stay at Solomons Inn Resort & Marina in Solomons, you'll be within a 15-minute drive of Patuxent River Naval Air Station and Southern Branch Library.
Solomons Inn Resort & Marina
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

3 out of 5
22769 Three Notch Rd, California, MD
Fully refundableReserve now, pay when you stay
With a stay at La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent in California, you'll be within a 5-minute drive of Patuxent River Naval Air Station ...
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
When you stay at Rod 'N' Reel Resort in Chesapeake Beach, you'll be on the waterfront, just steps from Chesapeake Beach Railway Museum and 3 minutes by foot ...
Rod 'N' Reel Resort
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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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