Maryland Pet Friendly(346)
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
Comfort & Style: Chesapeake Bay Views, Beach, Pier, Spa!
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 20
$495 -
$695
per night
2 - 3 night Minimum Stay
- 5 BR,
- 3 BA,
- Sleeps 20
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
Pool, hot tub, big water views--what more could you ask for in a cottage
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 7
$583 -
$712
per night
2 - 7 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 7
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
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
1920's Restored Waterman's Cottage with Fantastic Views!
- 2 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 4
$392 -
$500
per night
2 - 3 night Minimum Stay
- 2 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 4
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
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
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
Private Cottage just outside St. Michaels with kayak and bikes included!
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 6
$490 -
$610
per night
2 - 3 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 6
Waterfront getaway cottage near St. Michaels, hot tub, kayaks
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$425 -
$550
per night
2 - 7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Lake Access Chalet-Short Walk to Slip ($200 Summer Discount)
- 5 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 12
$275 -
$475
per night
2 - 7 night Minimum Stay
- 5 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 12
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
100 Acre Farm Only Minutes From Deep Creek Lake And Wisp
- 4 Bedrooms,
- 4 Bathrooms, Sleeps 8
$335 -
$450
per night
2 night Minimum Stay
- 4 BR,
- 4 BA,
- Sleeps 8
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
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
Miller's Slip Away Chalet pampers you while you relax in luxury.
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 12
- 5 BR,
- 3 BA,
- Sleeps 12
Year Round Waterfront Estate / Family Reunions - Sleeps 26
- 7 Bedrooms,
- 6 Bathrooms,
- 1 Half Bath, Sleeps 26
- 7 BR,
- 6 BA,
- 1 HF BA,
- Sleeps 26
Red Run Cabin at Deep Creek Lake
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
- 3 BR,
- 2 BA,
- Sleeps 6
Tucked in the Woods at Deep Creek Lake -Red Pine
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 10
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 10
Magical Bayfront Home
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$350 -
$425
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 8
Walk to DWTN or enjoy the FREE eCruiser! Great location!
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$500
per night
3 night Minimum Stay
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
Riverfront Cabin - 7 acres! Close to Hiking/State Parks!
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$200 -
$250
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 8
Total Privacy and Relaxation! 90 Acre Waterfront Farm with wraparound views
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 8
$492 -
$750
per night
2 - 7 night Minimum Stay
- 4 BR,
- 2 BA,
- Sleeps 8
1940's Sears Cottage in Village
- 2 Bedrooms,
- 1 Bathroom, Sleeps 4
$307 -
$360
per night
2 - 3 night Minimum Stay
- 2 BR,
- 1 BA,
- Sleeps 4