Stevensville Holiday Homes from £90: Search Holiday Homes in Stevensville

A pier extending into a body of water with people fishing, a clear sky, and distant land with a bridge.

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Our top choices for Stevensville holiday homes

A lighthouse with a white exterior, a balcony, and a metal roof.

1. Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

Michelle P.

includes taxes & fees

29 Sept - 30 Sept

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

2. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

Dawn G.

includes taxes & fees

29 Sept - 30 Sept

Three birds perched on a wooden structure by the water.

3. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

barbara s.

includes taxes & fees

29 Sept - 30 Sept

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

4. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

David R.

includes taxes & fees

29 Sept - 30 Sept

A two-story house with a red roof, a brick chimney, and a small porch.

5. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

"We arrived and the air conditioning was broken.The owner did not inform us but installed portable AC’s running vents out of doors that would not close or lock. The old AC unit was installed incorrectly &BR below flooded by 12 am. contacted owner and then was told not to run AC & we would be refunded. Covered mattresses that were being soaked, cleaned up flood, washed all bedding. Owner said trying to find us another rental but there were none & I had service dog. If we moved we would miss...

Suzanne R.

includes taxes & fees

30 Sept - 1 Oct

A building with a gabled roof and a circular vent on the roof.

6. BAYSIDE BUNGALOW

Rock Hall

Diane V.

includes taxes & fees

29 Sept - 30 Sept

A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

7. Large 2 bedroom house with private parking in a nice neighborhood

Arnold

Linda B.

includes taxes & fees

1 Oct - 2 Oct

A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

8. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

Robin

includes taxes & fees

29 Sept - 30 Sept

A beach with chairs and a pier in the background.

9. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Sharon Z.

includes taxes & fees

29 Sept - 30 Sept

A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

10. Lower Level Loft - Adorable Studio Apt. Near BWI

South Gate

Deanna

includes taxes & fees

29 Sept - 30 Sept

A wooden dock extending into a calm body of water with boats docked at the end.

11. Cozy 2br home w/ parking in downtown Annapolis

Historic District

Nancy N.

includes taxes & fees

5 Oct - 6 Oct

A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

12. Cute, Cozy 2-bedroom house near Annapolis with water access

Herald Harbor

Taylor C.

includes taxes & fees

12 Oct - 13 Oct

A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

13. Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

includes taxes & fees

29 Sept - 30 Sept

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

14. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

20 Oct - 21 Oct

A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

15. Charming Annapolis WaterVIEW Home

Arundel on the Bay

Whitney M.

includes taxes & fees

29 Sept - 30 Sept

A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

16. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Annapolis

includes taxes & fees

5 Oct - 6 Oct

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

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

North Beach

Johanna S.

includes taxes & fees

4 Oct - 5 Oct

A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

18. Historic Row Home in Downtown Annapolis

Historic District

"This property was an up and down property for us. The ups: check in process was flawless; cleanliness was as good as an old house can be; and the location was superb. The downs: they say it can sleep ten. Well ten people might sleep but they can’t do much else. There are two baths and the kitchen was fine and although adequate to work with. But there are only four wine glasses and barely five people can sit at the dining room table. So if ten people sleep - they wake up and there are enough...

DEAN F.

includes taxes & fees

29 Sept - 30 Sept

A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

19. Luxe Row Home Steps to USNA Gate 3!

Historic District

Christine A.

includes taxes & fees

29 Sept - 30 Sept

20. Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic District

Tracie B.

includes taxes & fees

29 Sept - 30 Sept

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Top Stevensville Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"The beds were comfortable. Amenities were plentiful. Enjoyed the stay. The shuttle driver John was great, and friendly. Would come back again."

Sonesta ES Suites Annapolis

10/10 Excellent

"We stayed in the 2 bedroom and there was plenty of room. Loved that each bedroom had a bathroom. It felt more lime staying in an apartment having your own entrance. Not having to worry about breakfast was a plus, really liked that it was included. The staff was very helpful. We did use the exercise room that was small but good enough for a quick workout to start the day. We would most definitely stay again."