Maryland Vacation Home Rentals(639)
Spacious Annapolis Waterfront Home with Multiple Decks, Private Pier, and Views!
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 10
$350 -
$500
per night
2 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 10
Annapolis/Boaters/ Waterfront,Pool,Beach,Slip, WI FI ,Family/Retreat
- 5 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 15
$400 -
$975
per night
2 - 3 night Minimum Stay
- 5 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 15
Amazing Waterfront in Annapolis, easy walk to Navy Stadium & Downtown
- 4 Bedrooms,
- 4 Bathrooms, Sleeps 13
$500 -
$1,200
per night
- 4 BR,
- 4 BA,
- Sleeps 13
Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
$650 -
$700
per night
2 - 3 night Minimum Stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Annapolis Area Severn River Waterfront
- 5 Bedrooms,
- 2 Bathrooms,
- 2 Half Baths, Sleeps 11
$500
per night
4 night Minimum Stay
- 5 BR,
- 2 BA,
- 2 HF BA,
- Sleeps 11
Downtown/Camden Yards- 600 feet from homeplate
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 9
$350
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 9
Stunning Downtown Home Steps From the Academy!
- 3 Bedrooms,
- 3 Bathrooms,
- 2 Half Baths, Sleeps 9
$750 -
$875
per night
2 night Minimum Stay
- 3 BR,
- 3 BA,
- 2 HF BA,
- Sleeps 9
It is all about the view - Updated, Decks, Shaded Back Yard, Dock
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$495 -
$605
per night
3 night Minimum Stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
Renovated Historic Home Located Downtown -Walk Everywhere!
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
- 3 BR,
- 2 BA,
- Sleeps 8
Beautiful Annapolis Getaway - Walk Everywhere!
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$300 -
$400
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 8
Ultimate family vacation home! Pool, dock, games barn, hot tub and more!
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$1,118 -
$1,185
per night
2 - 7 night Minimum Stay
- 5 BR,
- 4 BA,
- Sleeps 10
Beautiful Renovation in Historic District
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$375 -
$425
per night
2 - 30 night Minimum Stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
Easy to Love, Hard to Leave
- 7 Bedrooms,
- 7 Bathrooms,
- 1 Half Bath, Sleeps 22
$1,038 -
$1,318
per night
2 - 7 night Minimum Stay
- 7 BR,
- 7 BA,
- 1 HF BA,
- Sleeps 22
Luxury Waterfront Home, Sunsets, Pool, 2 miles from Town Center!
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$650 -
$800
per night
2 - 7 night Minimum Stay
- 5 BR,
- 4 BA,
- Sleeps 10
Camden Yards, Convention Center, Inner Harbor, Ravens Stadium
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 9
- 3 BR,
- 2 BA,
- Sleeps 9
Renovated Waterfront Farm House on 25 Acres with Pool
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$742 -
$868
per night
2 - 7 night Minimum Stay
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
Contemporary Cottage on quiet creek, waterside pool, tranquil views
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$675 -
$775
per night
2 - 7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 8
Three level family home restored 1920s Colonial on 25 acres, dock, pool
- 5 Bedrooms,
- 4 Bathrooms,
- 1 Half Bath, Sleeps 13
$742 -
$912
per night
2 - 7 night Minimum Stay
- 5 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 13
Sprawling Multi-Family Home with all the best amenities--pool, hot tub, dock, kayaks and more!
- 6 Bedrooms,
- 6 Half Baths, Sleeps 23
- 6 BR,
- 6 HF BA,
- Sleeps 23
Friends & Family "Crash Pad" - Views, Pool, Kayaks, Bikes, Firepit & More
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$727 -
$865
per night
2 - 7 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 8
Updated Historic Sprawling Waterfront Estate minutes to Oxford
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 10
$702 -
$978
per night
2 - 7 night Minimum Stay
- 5 BR,
- 3 BA,
- Sleeps 10
Newly remodeled 6 (plus) Bedroom / 7 Bath Vacation Home With Indoor Pool
- 6 Bedrooms,
- 7 Bathrooms, Sleeps 20
$700 -
$850
per night
2 night Minimum Stay
- 6 BR,
- 7 BA,
- Sleeps 20
Wow! Secluded waterfront home on Maryland's Charming Eastern Shore
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 8
$750
per night
3 - 7 night Minimum Stay
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 8
Special $1,000 Off May and June Weeks
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$800
per night
2 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 10
2 Weeks Still Open in June - $2000 Off $6300/Week!
- 6 Bedrooms,
- 6 Bathrooms,
- 2 Half Baths, Sleeps 12
$4,900
per week
2 night Minimum Stay
- 6 BR,
- 6 BA,
- 2 HF BA,
- Sleeps 12
In the Heart of Chesapeake Bay on Maryland’s Scenic Eastern Shore
- 7 Bedrooms,
- 7 Bathrooms,
- 1 Half Bath, Sleeps 14
$2,000 -
$2,500
per week
3 night Minimum Stay
- 7 BR,
- 7 BA,
- 1 HF BA,
- Sleeps 14
Year Round Waterfront Home w/Dock & Pool Sleeps 18
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 18
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 18
Artist Beach Home, Gorgeous 4 BR+ with Dock Bay Front
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 12
- 4 BR,
- 3 BA,
- Sleeps 12
Charming Island Home on Chesapeake Bay with Great Water Views
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$185
per night
3 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
McDade House-privacy In The Woods
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
- 3 BR,
- 2 BA,
- Sleeps 6