St. Leonard, MD Vacation Homes from AED 931

A beach at sunset with a wooden fence in the background.

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Our top choices for St. Leonard vacation homes

1. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

AED 931 total

includes taxes & fees

30 Sep - 1 Oct

2. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Bryan P.

AED 1,659 total

includes taxes & fees

20 Sep - 21 Sep

3. Bright and airy waterfront getaway

Benedict

George

AED 1,258 total

includes taxes & fees

20 Sep - 21 Sep

4. Plum Point Cottage #17

Huntingtown

AED 1,681 total

includes taxes & fees

21 Sep - 22 Sep

5. Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

Johanna S.

AED 1,338 total

includes taxes & fees

28 Sep - 29 Sep

6. 4-BR Waterfront Turret Home

Solomons

Thomas S.

AED 2,551 total

includes taxes & fees

21 Sep - 22 Sep

7. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lusby

Anonymous traveler

AED 3,126 total

includes taxes & fees

28 Sep - 29 Sep

8. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Penny N.

AED 1,552 total

includes taxes & fees

23 Sep - 24 Sep

9. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

Tanya S.

AED 4,423 total

includes taxes & fees

21 Sep - 22 Sep

10. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Lusby

Sarah R.

AED 3,446 total

includes taxes & fees

29 Sep - 30 Sep

11. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Lexington Park

Andrea B.

AED 1,351 total

includes taxes & fees

28 Sep - 29 Sep

Coffee/tea maker, fridge, microwave, oven

12. Waterfront Getaway with Dock

Woolford

Meagan G.

AED 981 total

includes taxes & fees

20 Oct - 21 Oct

13. Rose Haven Coastal Cottage

North Beach

Sharon t.

AED 1,591 total

includes taxes & fees

21 Sep - 22 Sep

14. Sunset Breezes - quiet waterfront retreat

Dorchester County

John C.

AED 1,788 total

includes taxes & fees

27 Sep - 28 Sep

15. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

Jill C.

AED 2,317 total

includes taxes & fees

20 Oct - 21 Oct

16. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

Ramon A.

AED 2,640 total

includes taxes & fees

6 Oct - 7 Oct

17. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Montross

Julie P.

AED 1,730 total

includes taxes & fees

28 Sep - 29 Sep

18. Charming Waterfront 3-bedroom house in Piney Point

Piney Point

Meira

AED 2,769 total

includes taxes & fees

19 Oct - 20 Oct

Smart TV, fireplace, computer monitors, printers

19. Tranquil Modern Farmhouse

Waldorf

Jay W.

AED 3,196 total

includes taxes & fees

20 Oct - 21 Oct

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Top St. Leonard Hotel Reviews

Rod 'N' Reel Resort

10/10 Excellent

"Me and my husband loved it. It was great., and for the most part pretty clean, but there was random hairs in our shower and glitter on the bathroom floor when we arrived. I didn’t complain to staff because overall, it was fairly clean. But all the other amenities and the resort as a whole is an excellent place to stay in a great price."

Wylder Tilghman Island

8/10 Good

"Property is well maintained and clean. The rooms are small but adequate. Our only fault was the restaurant pricing. Dishes are at least 25 to 40 percent upvharged. For example, a bowl of gazpacho was priced at $18 . If crab eas added it would have been $15 more for a grand total of $33 for a bowl of soup. Outrageous. I’ve been to 5 star restaurants and never paid that much for a bowl of soup. The chicken entree was $30 and the chicken consisted of 2 small chicken finger type pieces. No full breast or thigh/leg. Drinks definitely upcheged. Drive a bit down the road and eat at Chesapeake seafood or drive into town. If you don’t feel comfortable driving at night, go in and have a late lunch or get takeout."

Historic 1825 Chesapeake Farm Stay

10/10 Excellent

"I booked a weekend stay here for my wife and I for our 30th anniversary. The house was amazing. There has been a lot of effort put into its decor which adds plenty of character to this historic hosue.Its very warm and welcoming. We were greeted by Holly upon our arrival she made us feel comfortable immediately. She prepares a continental breakfast every morning that sets the bar for how others should be.( everything was delicious)There are plenty of areas to hang out comfortably inside as well as outside the house. We did not take advantage of wonderful pool table while we were there,maybe on the next trip.The house is located in a quiet area and it was very peaceful,it was a welcome break from our hectic everyday life. This bed and breakfast is located conveniently to a lot of local attractions ex. Calvert Cliffs, Calvert Marine Museum, Solomons Island etc. I would highly recommend this place to anyone looking for a place to stay in this area. My biggest complaint is that we enjoyed it so much that we didn't want leave and return to normal everyday life after the relaxing weekend we spent there."

Spark by Hilton California Lexington Park

8/10 Good

"The room was very clean and quiet throughout the night, Breakfast staff was very friendly and accommodating. I wish there was more of a variety for breakfast. Fresh fruit and cooked eggs would have been nice. Overall good stay. I would recommend staying here."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for St. Leonard vacation homes

1. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

2. Family Beach House: Spacious Deck, Grill & Views

3. Bright and airy waterfront getaway

4. Plum Point Cottage #17

5. Beachside Oasis with Beach Passes & King Suite by A Haven Away

6. 4-BR Waterfront Turret Home

7. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

8. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

9. Lakefront Cabin Near Solomons Island w/ Hot Tub

10. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

11. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

12. Waterfront Getaway with Dock

13. Rose Haven Coastal Cottage

14. Sunset Breezes - quiet waterfront retreat

15. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

16. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

17. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

18. Charming Waterfront 3-bedroom house in Piney Point

19. Tranquil Modern Farmhouse

Find vacation rentals that suit your style

Top St. Leonard Hotel Reviews

Rod 'N' Reel Resort

Wylder Tilghman Island

Comfort Inn & Suites Lexington Park near Pax River

Springhill Suites by Marriott Prince Frederick

Hilton Garden Inn Solomons

Historic 1825 Chesapeake Farm Stay

Sleep Inn & Suites California MD

Island Inn & Suites, an Ascend Collection Hotel

Spark by Hilton California Lexington Park

Search Vacation Homes in St. Leonard

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for St. Leonard vacation homes

1. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

2. Family Beach House: Spacious Deck, Grill & Views

3. Bright and airy waterfront getaway

4. Plum Point Cottage #17

5. Beachside Oasis with Beach Passes & King Suite by A Haven Away

6. 4-BR Waterfront Turret Home

7. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

8. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

9. Lakefront Cabin Near Solomons Island w/ Hot Tub

10. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

11. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

12. Waterfront Getaway with Dock

13. Rose Haven Coastal Cottage

14. Sunset Breezes - quiet waterfront retreat

15. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

16. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

17. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

18. Charming Waterfront 3-bedroom house in Piney Point

19. Tranquil Modern Farmhouse

Find vacation rentals that suit your style

Top St. Leonard Hotel Reviews

Rod 'N' Reel Resort

15. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8