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Vacation Rentals
>
World
>
USA
>
Maryland
5
BR /
4
BA /
1
HF BA /
Sleeps
12
From $395/nt
Featured
3
BR /
1
BA /
Sleeps
6
From $225/nt
Featured
3
BR /
2
BA /
1
HF BA /
Sleeps
10
From $129/nt
Featured
3
BR /
2
BA /
Sleeps
8
From $350/nt
Featured
3
BR /
2
BA /
Sleeps
6
From $408/nt
Featured
Maryland Waterfront Vacation Rentals
(823)
sort by
HomeAway Sort
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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
Spacious Annapolis Waterfront Home with Multiple Decks, Private Pier, and Views!
3 Bedrooms,
3
Bathrooms
, Sleeps 10
$350 - $500
per night
Spacious Annapolis Waterfront Home with Multiple Decks, Private Pier, and Views!
Book it Now!
2 night minimum stay
3
BR,
3
BA,
Sleeps
10
Maryland
>
Annapolis House
#968476
(20)
Compare
Annapolis/Boaters/ Waterfront,Pool,Beach,Slip, wifi ,Family/Retreat
5 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 15
$400 - $975
per night
Annapolis/Boaters/ Waterfront,Pool,Beach,Slip, wifi ,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
Belmont Towers Direct Oceanfront/Boardwalk-Gorgeous! only 1 summer week avail.
3 Bedrooms,
3
Bathrooms
, Sleeps 9
$200 - $850
per night
Belmont Towers Direct Oceanfront/Boardwalk-Gorgeous! only 1 summer week avail.
Book it Now!
2 - 7 night minimum stay
3
BR,
3
BA,
Sleeps
9
Ocean City
>
Belmont Towers Ocean City Condo
#233143
(66)
Compare
Belmont Towers Premier Boardwalk/Oceanfront! Mini weeks and weekend available.
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 9
$175 - $750
per night
Belmont Towers Premier Boardwalk/Oceanfront! Mini weeks and weekend available.
2 - 4 night minimum stay
3
BR,
2
BA,
1
HF BA,
Sleeps
9
Ocean City
>
Belmont Towers Ocean City Condo
#187487
(88)
Compare
Annapolis Area Severn River Waterfront
5 Bedrooms,
2
Bathrooms
,
2
Half Baths
, Sleeps 11
$500
per night
Annapolis Area Severn River Waterfront
4 night minimum stay
5
BR,
2
BA,
2
HF BA,
Sleeps
11
Maryland
>
Annapolis House
#360959
(10)
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
(18)
Compare
Amazing Waterfront in Annapolis, easy walk to Navy Stadium & Downtown
4 Bedrooms,
4
Bathrooms
, Sleeps 14
$500 - $1,200
per night
Amazing Waterfront in Annapolis, easy walk to Navy Stadium & Downtown
4
BR,
4
BA,
Sleeps
14
Maryland
>
Annapolis House
#241350
(13)
Compare
Pool, hot tub, big water views--what more could you ask for in a cottage
3 Bedrooms,
3
Bathrooms
, Sleeps 7
$567 - $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
(39)
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
(10)
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
$730 - $872
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
Spectacular Corner Unit - Direct Waterfront Condo in Crisfield, Md
3 Bedrooms,
2
Bathrooms
, Sleeps 6
$100 - $200
per night
Spectacular Corner Unit - Direct Waterfront Condo in Crisfield, Md
3 night minimum stay
3
BR,
2
BA,
Sleeps
6
Chesapeake Bay
>
Crisfield Condo
#277457
(49)
Compare
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
It is all about the view - Updated, Decks, Shaded Back Yard, Dock
3 night minimum stay
3
BR,
2
BA,
1
HF BA,
Sleeps
6
Chesapeake Bay
>
Tilghman Island House
#78928vb
(4)
Compare
Sprawling Multi-Family Home with all the best amenities--pool, hot tub, dock, kayaks and more!
6 Bedrooms,
6
Half Baths
, Sleeps 23
Sprawling Multi-Family Home with all the best amenities--pool, hot tub, dock, kayaks and more!
6
BR,
6
HF BA,
Sleeps
23
Chesapeake Bay
>
Cambridge House
#922769
(40)
Compare
Ultimate family vacation home! Pool, dock, games barn, hot tub and more!
5 Bedrooms,
4
Bathrooms
, Sleeps 10
$1,118 - $1,185
per night
Ultimate family vacation home! Pool, dock, games barn, hot tub and more!
2 - 7 night minimum stay
5
BR,
4
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#922712
(15)
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
Luxury Waterfront Home....ONE SUMMER WEEK LEFT 6/23-6/30
5 Bedrooms,
4
Bathrooms
, Sleeps 10
$650 - $800
per night
Luxury Waterfront Home....ONE SUMMER WEEK LEFT 6/23-6/30
2 - 7 night minimum stay
5
BR,
4
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#233398
(13)
Compare
Luxury Ocean Facing 2 BR Condo,Slps 8,Indoor Pool,Walk 2 Beach
2 Bedrooms,
2
Bathrooms
, Sleeps 8
$83 - $258
per night
Luxury Ocean Facing 2 BR Condo,Slps 8,Indoor Pool,Walk 2 Beach
3 night minimum stay
2
BR,
2
BA,
Sleeps
8
Ocean City
>
Makai Ocean City Condo
#413468vb
(8)
Compare
Updated Historic Sprawling Waterfront Estate minutes to Oxford
5 Bedrooms,
3
Bathrooms
, Sleeps 10
$717 - $993
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
(5)
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
Boaters Delight, Spectacular Sunsets!
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$1,300 - $2,200
per week
Boaters Delight, Spectacular Sunsets!
7 night minimum stay
3
BR,
2
BA,
Sleeps
8
Ocean City
>
Vacation Homes in Ocean City Townhome
#102006
(18)
Compare
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
2 Bedrooms,
2
Bathrooms
, Sleeps 4
$950 - $2,395
per week
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
3 - 7 night minimum stay
2
BR,
2
BA,
Sleeps
4
Ocean City
>
Capri Ocean City Condo
#250023
(33)
Compare
Gorgeous Southern Colonial on the Water in Annapolis-
6 Bedrooms,
4
Bathrooms
,
1
Half Bath
, Sleeps 16
Gorgeous Southern Colonial on the Water in Annapolis-
6
BR,
4
BA,
1
HF BA,
Sleeps
16
Maryland
>
Annapolis Cottage
#283672
(44)
Compare
Charming Island Home on Chesapeake Bay with Great Water Views
3 Bedrooms,
2
Bathrooms
, Sleeps 6
Charming Island Home on Chesapeake Bay with Great Water Views
3
BR,
2
BA,
Sleeps
6
Chesapeake Bay
>
Tilghman Island House
#274622
Compare
Luxury St. Michaels Waterfront 6 Bedrooms/6 Baths $4900/Week
6 Bedrooms,
6
Bathrooms
,
2
Half Baths
, Sleeps 12
$4,900
per week
Luxury St. Michaels Waterfront 6 Bedrooms/6 Baths $4900/Week
2 night minimum stay
6
BR,
6
BA,
2
HF BA,
Sleeps
12
Chesapeake Bay
>
St. Michaels House
#272472
Compare
Direct OceanFront; Discounts for May weeks. Weekends available.
2 Bedrooms,
2
Bathrooms
, Sleeps 7
$225
per night
Direct OceanFront; Discounts for May weeks. Weekends available.
3 night minimum stay
2
BR,
2
BA,
Sleeps
7
Ocean City
>
Atlantis Ocean City Condo
#114347
(5)
Compare
Beachfront Resort Condo w/ Gr8 Views - WiFi, Pools, Game Room & More!
3 Bedrooms,
3
Bathrooms
, Sleeps 6
$2,695 - $4,395
per week
Beachfront Resort Condo w/ Gr8 Views - WiFi, Pools, Game Room & More!
7 night minimum stay
3
BR,
3
BA,
Sleeps
6
Ocean City
>
Gateway Grand Ocean City Condo
#3000962
Compare
Luxurious 'Cottage by the Sea' Oceanfront Condo SIZZLING SUMMER SALE!
3 Bedrooms,
3
Bathrooms
, Sleeps 10
$2,100 - $6,195
per week
Luxurious 'Cottage by the Sea' Oceanfront Condo SIZZLING SUMMER SALE!
7 night minimum stay
3
BR,
3
BA,
Sleeps
10
Ocean City
>
Gateway Grand Ocean City Condo
#249999
(14)
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
Just Reduced! Oceanfront Perfection — Huge Luxury Condo w/ Wi-Fi & Pool!
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 12
$495 - $1,395
per night
Just Reduced! Oceanfront Perfection — Huge Luxury Condo w/ Wi-Fi & Pool!
3 - 7 night minimum stay
4
BR,
3
BA,
1
HF BA,
Sleeps
12
Ocean City
>
Meridian Ocean City Condo
#3530540
4 Reviews
Compare
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Maryland
Annapolis (39)
Baltimore (11)
Berlin (1)
Bryans Road (2)
Chesapeake Bay (210)
Edgewater (2)
Lexington Park (1)
Maryland - Washington DC (9)
Ocean City (456)
Ocean Pines (19)
Pasadena (1)
Western Maryland (71)
West Ocean City (1)