HomeAway Vacation Rentals
Traveler Login
Owner Login
Viewed
Favorites
Inquired
My Trips
My Profile
Owner Dashboard
Logout
Help
Travelers
How it Works
Community
Help
Homeowners
How it Works
List Your Property
Community
Help
Property Managers
How it Works
Help
List Your Property
Search
You have sent
a request for
information to
this owner.
FILTERS
List View
Map View
Cancel
Apply Filters
Clear Filters
FILTERS
346
Results
Location
Maryland
Property Manager
Price
Price Per Week
$
Any
0
750
1,000
1,250
1,500
2,000
3,000
4,000
5,000
6,000
7,000
8,000
9,000
$
Any
750
1,000
1,250
1,500
2,000
3,000
4,000
5,000
6,000
7,000
8,000
9,000
10,000
Clear
Sleeps
Any
1+
(
536,412
)
2+
(
536,152
)
3+
(
512,308
)
4+
(
497,869
)
5+
(
395,243
)
6+
(
358,971
)
7+
(
228,590
)
8+
(
206,854
)
9+
(
122,193
)
10+
(
109,744
)
11+
(
65,058
)
12+
(
59,157
)
13 or more
(
34,851
)
Bedrooms
Any
Studio
(
22,303
)
1
(
88,567
)
2
(
162,609
)
3
(
142,498
)
4
(
76,310
)
5
(
32,168
)
6+
(
23,721
)
Booking
Book Online
(
27
)
Accepts online payments
(
101
)
More Filters
Hide Filters
Annapolis (38)
Baltimore (10)
Berlin (2)
Chesapeake Bay (148)
Edgewater (1)
Frederick (4)
Havre de Grace (1)
Lexington Park (1)
Maryland - Washington DC (16)
Middletown (1)
Ocean City (42)
Ocean Pines (8)
Western Maryland (74)
Price Per Week
$
$
Sleeps
Bedrooms
Bathrooms
Booking Options
Booking Options
Book Online
(
27
)
Accepts online payments
(
101
)
Property Type (Select Multiple)
Property Type
Apartments
Apartments
(
7
)
Bungalows
Bungalows
(
2
)
Cabins
Cabins
(
15
)
Chalets
Chalets
(
7
)
Condos
Condos
(
33
)
Cottages
Cottages
(
49
)
Estates
Estates
(
9
)
Farmhouses
Farmhouses
(
8
)
Hotels
Hotels
(
1
)
Homes
Homes
(
195
)
Lodges
Lodges
(
2
)
Studios
Studios
(
1
)
Townhomes
Townhomes
(
14
)
Villas
Villas
(
1
)
Yachts
Yachts
(
1
)
Barns
Barns
(
0
)
Castles
Castles
(
0
)
Location Type
Location Type
beach
(
67
)
waterfront
(
154
)
near the ocean
(
44
)
lake
(
38
)
downtown
(
16
)
mountain
(
39
)
river
(
24
)
golf
(
263
)
skiing
(
60
)
Even More Filters
Even More Filters
special deals & offers
(
2
)
long term renters welcome
(
78
)
luxury
(
31
)
budget
(
26
)
Featured Listing
(
44
)
1+ reviews
(
239
)
Features
Features
Pool
(
107
)
Internet Access
(
276
)
Satellite or Cable TV
(
273
)
Pets Considered
(
-1
)
wheelchair accessible
(
32
)
Hot Tub
(
81
)
Air Conditioning
(
313
)
non smoking only
(
281
)
Fireplace
(
207
)
Parking Included
(
282
)
Outdoor Grill
(
270
)
Managed By
Managed By
Owner
(
242
)
Property Manager
(
104
)
Any
Cancel
Clear Filters
Apply Filters
Vacation Rentals
>
World
>
USA
>
Maryland
4
BR /
2
BA /
Sleeps
8
From $492/nt
Featured
6
BR /
6
HF BA /
Sleeps
23
Featured
1
BR /
1
BA /
Sleeps
4
From $650/wk
Featured
2
BR /
2
BA /
Sleeps
4
From $950/wk
Featured
2
BR /
2
BA /
Sleeps
8
From $150/nt
Featured
Maryland Pet Friendly
(346)
sort by
HomeAway Sort
HomeAway Sort
Average Rating
Availability Last Updated
Accepts Online Payments
Bedrooms: Least to Most
Bedrooms: Most to Least
Price: High to Low
Price: Low to High
Number of Reviews
Special Offers First
Annapolis/Boaters/ Waterfront,Pool,Beach,Slip, WI FI ,Family/Retreat
5 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 15
$400 - $975
per night
Annapolis/Boaters/ Waterfront,Pool,Beach,Slip, WI FI ,Family/Retreat
Book it Now!
2 - 3 night Minimum Stay
5
BR,
2
BA,
1
HF BA,
Sleeps
15
Maryland
>
Annapolis House
#223105
(32)
Compare
Comfort & Style: Chesapeake Bay Views, Beach, Pier, Spa!
5 Bedrooms,
3
Bathrooms
, Sleeps 20
$495 - $695
per night
Comfort & Style: Chesapeake Bay Views, Beach, Pier, Spa!
Book it Now!
2 - 3 night Minimum Stay
5
BR,
3
BA,
Sleeps
20
Maryland
>
Annapolis Cottage
#390303vb
(23)
Compare
Amazing Waterfront in Annapolis, easy walk to Navy Stadium & Downtown
4 Bedrooms,
4
Bathrooms
, Sleeps 13
$500 - $1,200
per night
Amazing Waterfront in Annapolis, easy walk to Navy Stadium & Downtown
4
BR,
4
BA,
Sleeps
13
Maryland
>
Annapolis House
#241350
(12)
Compare
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
Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly
2 - 3 night Minimum Stay
4
BR,
2
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#123352
(17)
Compare
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
Pool, hot tub, big water views--what more could you ask for in a cottage
2 - 7 night Minimum Stay
3
BR,
3
BA,
Sleeps
7
Chesapeake Bay
>
Tilghman Island Cottage
#204687vb
(38)
Compare
Easy to Love, Hard to Leave
7 Bedrooms,
7
Bathrooms
,
1
Half Bath
, Sleeps 22
$1,038 - $1,318
per night
Easy to Love, Hard to Leave
2 - 7 night Minimum Stay
7
BR,
7
BA,
1
HF BA,
Sleeps
22
Chesapeake Bay
>
Church Creek House
#390476vb
(10)
Compare
Renovated Historic Home Located Downtown -Walk Everywhere!
3 Bedrooms,
2
Bathrooms
, Sleeps 8
Renovated Historic Home Located Downtown -Walk Everywhere!
3
BR,
2
BA,
Sleeps
8
Maryland
>
Annapolis House
#951256
(28)
Compare
Beautiful Annapolis Getaway - Walk Everywhere!
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$300 - $400
per night
Beautiful Annapolis Getaway - Walk Everywhere!
2 night Minimum Stay
3
BR,
2
BA,
Sleeps
8
Maryland
>
Annapolis House
#461541vb
(4)
Compare
1920's Restored Waterman's Cottage with Fantastic Views!
2 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 4
$392 - $500
per night
1920's Restored Waterman's Cottage with Fantastic Views!
2 - 3 night Minimum Stay
2
BR,
1
BA,
1
HF BA,
Sleeps
4
Chesapeake Bay
>
Tilghman Island Cottage
#922752
(51)
Compare
Renovated Waterfront Farm House on 25 Acres with Pool
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 10
$742 - $868
per night
Renovated Waterfront Farm House on 25 Acres with Pool
2 - 7 night Minimum Stay
4
BR,
3
BA,
1
HF BA,
Sleeps
10
Chesapeake Bay
>
Cambridge House
#367564vb
(11)
Compare
Contemporary Cottage on quiet creek, waterside pool, tranquil views
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$675 - $775
per night
Contemporary Cottage on quiet creek, waterside pool, tranquil views
2 - 7 night Minimum Stay
3
BR,
2
BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#391798vb
(21)
Compare
Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location
4 Bedrooms,
3
Bathrooms
, Sleeps 8
$535 - $752
per night
Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location
2 - 7 night Minimum Stay
4
BR,
3
BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels Cottage
#449007vb
(8)
Compare
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
Three level family home restored 1920s Colonial on 25 acres, dock, pool
2 - 7 night Minimum Stay
5
BR,
4
BA,
1
HF BA,
Sleeps
13
Chesapeake Bay
>
Cambridge House
#390372vb
(10)
Compare
Private Cottage just outside St. Michaels with kayak and bikes included!
3 Bedrooms,
3
Bathrooms
, Sleeps 6
$490 - $610
per night
Private Cottage just outside St. Michaels with kayak and bikes included!
2 - 3 night Minimum Stay
3
BR,
3
BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels Cottage
#389515vb
(11)
Compare
Waterfront getaway cottage near St. Michaels, hot tub, kayaks
3 Bedrooms,
2
Bathrooms
, Sleeps 6
$425 - $550
per night
Waterfront getaway cottage near St. Michaels, hot tub, kayaks
2 - 7 night Minimum Stay
3
BR,
2
BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels Cottage
#448997vb
(25)
Compare
Lake Access Chalet-Short Walk to Slip ($200 Summer Discount)
5 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 12
$275 - $475
per night
Lake Access Chalet-Short Walk to Slip ($200 Summer Discount)
2 - 7 night Minimum Stay
5
BR,
3
BA,
1
HF BA,
Sleeps
12
Deep Creek Lake
>
McHenry Chalet
#170908
(10)
Compare
Updated Historic Sprawling Waterfront Estate minutes to Oxford
5 Bedrooms,
3
Bathrooms
, Sleeps 10
$702 - $978
per night
Updated Historic Sprawling Waterfront Estate minutes to Oxford
2 - 7 night Minimum Stay
5
BR,
3
BA,
Sleeps
10
Chesapeake Bay
>
Oxford House
#922779
(4)
Compare
100 Acre Farm Only Minutes From Deep Creek Lake And Wisp
4 Bedrooms,
4
Bathrooms
, Sleeps 8
$335 - $450
per night
100 Acre Farm Only Minutes From Deep Creek Lake And Wisp
2 night Minimum Stay
4
BR,
4
BA,
Sleeps
8
Deep Creek Lake
>
McHenry Farmhouse
#455866vb
Compare
Wow! Secluded waterfront home on Maryland's Charming Eastern Shore
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 8
$750
per night
Wow! Secluded waterfront home on Maryland's Charming Eastern Shore
3 - 7 night Minimum Stay
4
BR,
3
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
Centreville House
#458295vb
2 Reviews
Compare
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
In the Heart of Chesapeake Bay on Maryland’s Scenic Eastern Shore
3 night Minimum Stay
7
BR,
7
BA,
1
HF BA,
Sleeps
14
Chesapeake Bay
>
Tilghman Island House
#3513192
Compare
Year Round Waterfront Home w/Dock & Pool Sleeps 18
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 18
Year Round Waterfront Home w/Dock & Pool Sleeps 18
4
BR,
3
BA,
1
HF BA,
Sleeps
18
Chesapeake Bay
>
Cambridge House
#429253vb
(7)
Compare
Miller's Slip Away Chalet pampers you while you relax in luxury.
5 Bedrooms,
3
Bathrooms
, Sleeps 12
Miller's Slip Away Chalet pampers you while you relax in luxury.
5
BR,
3
BA,
Sleeps
12
Deep Creek Lake
>
McHenry Chalet
#448036vb
(3)
Compare
Year Round Waterfront Estate / Family Reunions - Sleeps 26
7 Bedrooms,
6
Bathrooms
,
1
Half Bath
, Sleeps 26
Year Round Waterfront Estate / Family Reunions - Sleeps 26
7
BR,
6
BA,
1
HF BA,
Sleeps
26
Chesapeake Bay
>
Cambridge Estate
#409548vb
(4)
Compare
Red Run Cabin at Deep Creek Lake
3 Bedrooms,
2
Bathrooms
, Sleeps 6
Red Run Cabin at Deep Creek Lake
3
BR,
2
BA,
Sleeps
6
Deep Creek Lake
>
McComas Beach Cabin
#444352vb
Compare
Tucked in the Woods at Deep Creek Lake -Red Pine
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 10
Tucked in the Woods at Deep Creek Lake -Red Pine
3
BR,
2
BA,
1
HF BA,
Sleeps
10
Deep Creek Lake
>
McHenry House
#374892vb
Compare
Magical Bayfront Home
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$350 - $425
per night
Magical Bayfront Home
2 night Minimum Stay
3
BR,
2
BA,
Sleeps
8
Chesapeake Bay
>
Port Republic House
#212770
(13)
Compare
Walk to DWTN or enjoy the FREE eCruiser! Great location!
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 10
$500
per night
Walk to DWTN or enjoy the FREE eCruiser! Great location!
3 night Minimum Stay
4
BR,
3
BA,
1
HF BA,
Sleeps
10
Maryland
>
Annapolis House
#319055
(26)
Compare
Riverfront Cabin - 7 acres! Close to Hiking/State Parks!
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$200 - $250
per night
Riverfront Cabin - 7 acres! Close to Hiking/State Parks!
Book it Now!
2 night Minimum Stay
3
BR,
2
BA,
Sleeps
8
Deep Creek Lake
>
Oakland Cabin
#377768
2 Reviews
Compare
Total Privacy and Relaxation! 90 Acre Waterfront Farm with wraparound views
4 Bedrooms,
2
Bathrooms
, Sleeps 8
$492 - $750
per night
Total Privacy and Relaxation! 90 Acre Waterfront Farm with wraparound views
2 - 7 night Minimum Stay
4
BR,
2
BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#146900vb
(26)
Compare
1940's Sears Cottage in Village
2 Bedrooms,
1
Bathroom
, Sleeps 4
$307 - $360
per night
1940's Sears Cottage in Village
2 - 3 night Minimum Stay
2
BR,
1
BA,
Sleeps
4
Chesapeake Bay
>
Oxford Cottage
#215987vb
(59)
Compare
1 - 30 of 346
Show
15
30
60
properties
Advertisement
Maryland
Annapolis (38)
Baltimore (10)
Berlin (2)
Chesapeake Bay (148)
Edgewater (1)
Frederick (4)
Havre de Grace (1)
Lexington Park (1)
Maryland - Washington DC (16)
Middletown (1)
Ocean City (42)
Ocean Pines (8)
Western Maryland (74)