Maryland with Pools(898)
Annapolis/Boaters/ Waterfront,Pool,Beach,Slip, wifi ,Family/Retreat
- 5 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 15
$250 -
$975
per night
2 - 3 night minimum stay
- 5 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 15
Belmont Towers Direct Oceanfront/Boardwalk Sept discounts for full week
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 9
$200 -
$850
per night
2 - 7 night minimum stay
- 3 BR,
- 3 BA,
- Sleeps 9
Comfort & Style: Chesapeake Bay Views, Beach, Pier, Spa!
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 20
$195 -
$695
per night
2 - 3 night minimum stay
- 5 BR,
- 3 BA,
- Sleeps 20
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
Oceanblock 3-Story Townhome with 2-Car Garage 56th Street
- 3 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$150 -
$500
per night
2 - 7 night minimum stay
- 3 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
Belmont Towers Premier Boardwalk/Oceanfront! Mini weeks and weekend available.
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 9
$175 -
$750
per night
2 - 4 night minimum stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 9
Pool, hot tub, big water views--what more could you ask for in a cottage
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 7
$587 -
$712
per night
2 - 7 night minimum stay
- 3 BR,
- 3 BA,
- Sleeps 7
Amazing Waterfront in Annapolis, easy walk to Navy Stadium & Downtown
- 4 Bedrooms,
- 4 Bathrooms, Sleeps 14
$500 -
$1,200
per night
- 4 BR,
- 4 BA,
- Sleeps 14
Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$535 -
$752
per night
2 - 7 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 8
Renovated Waterfront Farm House on 25 Acres with Pool
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$742 -
$872
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 -
$921
per night
2 - 7 night minimum stay
- 5 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 13
Friends & Family "Crash Pad" - Views, Pool, Kayaks, Bikes, Firepit & More
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$744 -
$869
per night
2 - 7 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 8
Spectacular Corner Unit - Direct Waterfront Condo in Crisfield, Md
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$100 -
$200
per night
3 night minimum stay
- 3 BR,
- 2 BA,
- Sleeps 6
Our Nation's Capitol -- Enjoy a beautiful historical vacation
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 8
$249 -
$269
per night
2 night minimum stay
- 2 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
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 Large Waterfront Home, Sunsets, Pool, 2 miles from town
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$650 -
$800
per night
2 - 7 night minimum stay
- 5 BR,
- 4 BA,
- Sleeps 10
Luxury Ocean Facing 2 BR Condo,Slps 8,Indoor Pool,Walk 2 Beach
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 8
$83 -
$258
per night
3 night minimum stay
- 2 BR,
- 2 BA,
- Sleeps 8
Updated Historic Sprawling Waterfront Estate minutes to Oxford
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 10
$717 -
$993
per night
2 - 7 night minimum stay
- 5 BR,
- 3 BA,
- Sleeps 10
Charming Island Home on Chesapeake Bay with Great Water Views
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
- 3 BR,
- 2 BA,
- Sleeps 6
Rudy's Retreat $ 129/Night + Community Indoor Heated Pool!!
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 10
$119 -
$129
per night
2 night minimum stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 10
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 4
$950 -
$2,395
per week
3 - 7 night minimum stay
- 2 BR,
- 2 BA,
- Sleeps 4
Luxury Bay View Condo, New Furnishings, Linens, Pool, Wi Fi & Walk to Beach
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 7
$120 -
$170
per night
3 night minimum stay
- 2 BR,
- 2 BA,
- Sleeps 7
St. Michaels Waterfront 5 Bedroom, Sleeps 10 $2,500/Week
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$357 -
$800
per night
2 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 10
Newly remodeled 6 (plus) Bedroom / 7.5 Bath Vacation Home With Indoor Pool
- 6 Bedrooms,
- 7 Bathrooms, Sleeps 20
$600 -
$850
per night
2 night minimum stay
- 6 BR,
- 7 BA,
- Sleeps 20
The Point of It All-Near Annapolis, Washington D.C., Baltimore
- 6 Bedrooms,
- 6 Bathrooms, Sleeps 14
$5,425 -
$6,475
per week
7 night minimum stay
- 6 BR,
- 6 BA,
- Sleeps 14
AWESOME BAYVIEWS! Direct Bayfront Topfloor Condo Sleep6
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 8
- 2 BR,
- 2 BA,
- Sleeps 8
Luxury St. Michaels Waterfront 6 Bedrooms/6 Baths $4900/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
Direct OceanFront; Discounts for May weeks. Weekends available.
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 7
$225
per night
3 night minimum stay
- 2 BR,
- 2 BA,
- Sleeps 7