Dorchester Area Vacation Rentals - Dorchester Area, Maryland Vacation Rental Deals on Lake Rentals, Beach Houses, Condos, Cabins, Villas by VacaGuru.com!

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

4
2.0
15

Cambridge Maryland Private vacation home From $513 per night (USD)

Algonquin on the Choptank River is a great getaway

Algonquin on the Choptank River is a great getaway

4
3.0
12

Cambridge Maryland Private vacation home From $354 per night (USD)

Beautiful Colonial Home on the Choptank River

Beautiful Colonial Home on the Choptank River

4
2.0
8

Cambridge Maryland Private vacation home From $533 per night (USD)

Waterfront Getaway with Dock

Waterfront Getaway with Dock

3
2.0
6

Woolford Maryland Private vacation home From $220 per night (USD)

Charming and Private with a Water view

Charming and Private with a Water view

1
1.0
3

Cambridge Maryland Private vacation home Click For Pricing

Indian Fields - 25-Acre Nature Lovers retreat!

Indian Fields - 25-Acre Nature Lovers retreat!

5
5.0
13

Cambridge Maryland Private vacation home From $550 per night (USD)

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat

3
4.0
8

Dorchester County Maryland Private vacation home From $224 per night (USD)

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

3
2.0
12

Cambridge Maryland Private vacation home From $595 per night (USD)

$Cambridge Home w\/ Private Dock ~ 4 Mi to Dtwn$

Cambridge Home w\/ Private Dock ~ 4 Mi to Dtwn

4
2.0
8

Cambridge Maryland Private vacation home From $398 per night (USD)

Tidal Serenity- Remote Waterfront Home with dock

Tidal Serenity- Remote Waterfront Home with dock

5
4.0
15

Taylors Island Maryland Private vacation home From $377 per night (USD)

$Waterfront Home, Large Property with Pool, Discount for Monthly\/Seasonal Rentals$

Waterfront Home, Large Property with Pool, Discount for Monthly\/Seasonal Rentals

5
4.0
16

Cambridge Maryland Private vacation home From $750 per night (USD)

$Historic 1918 House 1\/2 Block from the Choptank River$

Historic 1918 House 1\/2 Block from the Choptank River

1
2.0
6

Cambridge Maryland Private vacation home Click For Pricing

Riverside Lodge Bed & Breakfast on the Honga River UNIT B

Riverside Lodge Bed & Breakfast on the Honga River UNIT B

1
1.0
2

Fishing Creek Maryland Bed & breakfast From $270 per night (USD)

Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing

Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing

6
4.0
15

Cambridge Maryland Private vacation home Click For Pricing

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

1
1.0
2

Fishing Creek Maryland Private vacation home From $270 per night (USD)

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

1
1.0
2

Fishing Creek Maryland Private vacation home From $270 per night (USD)

$Waterfront Insta-Worthy Sunsets! 5BR w\/ Bikes , Kayaks and 🐾 Friendly$

Waterfront Insta-Worthy Sunsets! 5BR w\/ Bikes , Kayaks and 🐾 Friendly

5
3.0
15

Fishing Creek Maryland Private vacation home From $285 per night (USD)

Historic Hoopersville Getaway on Chesapeake Bay!

Historic Hoopersville Getaway on Chesapeake Bay!

7
3.0
18

Hoopersville Maryland Private vacation home From $260 per night (USD)

Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks

Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks

5
4.0
16

Cambridge Maryland Private vacation home From $745 per night (USD)

360° Water Views, Hoopers Island Vacation Studio, Fishing Creek

360° Water Views, Hoopers Island Vacation Studio, Fishing Creek

1
1.0
3

Fishing Creek Maryland Apartment From $172 per night (USD)

Need a vacation? Walk to the waterfront 🌊 at the Bungalow ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

Need a vacation? Walk to the waterfront 🌊 at the Bungalow ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

3
2.0
10

Fishing Creek Maryland Private vacation home From $900 per night (USD)

Riverside Lodge Bed & Breakfast on the Honga River UNIT A

Riverside Lodge Bed & Breakfast on the Honga River UNIT A

1
1.0
2

Fishing Creek Maryland Bed & breakfast From $245 per night (USD)

Waterside 4-Bedroom Chesapeake Styled Townhome

Waterside 4-Bedroom Chesapeake Styled Townhome

4
4.0
10

Cambridge Maryland Private vacation home Click For Pricing

Short drive to Downtown Cambridge | Sleeps 22 | Pool | Private Dock | Kayaks | P

Short drive to Downtown Cambridge | Sleeps 22 | Pool | Private Dock | Kayaks | P

7
6.0
22

Cambridge Maryland Private vacation home From $928 per night (USD)

Short drive to Downtown Cambridge | Private Dock | Sleeps 22 | Pool | Hot Tub |

Short drive to Downtown Cambridge | Private Dock | Sleeps 22 | Pool | Hot Tub |

9
6.0
22

East New Market Maryland Private vacation home From $2135 per night (USD)

Short drive to Downtown Cambridge | Pool | Private Dock | Game Room | Stunning V

Short drive to Downtown Cambridge | Pool | Private Dock | Game Room | Stunning V

7
7.0
20

Cambridge Maryland Private vacation home From $943 per night (USD)

Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18

Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18

5
5.0
18

Cambridge Maryland Private vacation home From $1050 per night (USD)

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

3
1.0
8

Cambridge Maryland Private vacation home From $442 per night (USD)

Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island

2
1.0
5

Fishing Creek Maryland Cottage From $203 per night (USD)

Dorchester County Home Near Choptank River!

Dorchester County Home Near Choptank River!

3
2.0
7

Cambridge Maryland Private vacation home From $271 per night (USD)

Private, gated country home with outdoor pavilion & EV charger - dog-friendly

Private, gated country home with outdoor pavilion & EV charger - dog-friendly

3
4.0
8

Hurlock Maryland Private vacation home From $326 per night (USD)

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

6
4.0
18

Woolford Maryland Private vacation home From $440 per night (USD)

$Cozy Cambridge Retreat w\/ Casita Near Marina!$

Cozy Cambridge Retreat w\/ Casita Near Marina!

4
3.0
10

Cambridge Maryland Private vacation home From $434 per night (USD)

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

2
3.0
5

Cambridge Maryland Private vacation home From $175 per night (USD)

Large Luxury Townhouse with Elevator adjacent to the Chesapeake Hyatt

Large Luxury Townhouse with Elevator adjacent to the Chesapeake Hyatt

4
4.0
10

Cambridge Maryland Private vacation home From $706 per night (USD)

Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach

Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach

4
3.0
12

Cambridge Maryland Private vacation home From $889 per night (USD)

$Chesapeake Waterfront- 7bd\/5ba, Beach, Pool, Pets, Dock - Free Night thru April$

Chesapeake Waterfront- 7bd\/5ba, Beach, Pool, Pets, Dock - Free Night thru April

7
5.0
18

Woolford Maryland Private vacation home From $1060 per night (USD)

Waterfront Getaway on the Choptank River

Waterfront Getaway on the Choptank River

2
1.0
6

Cambridge Maryland Private vacation home From $200 per night (USD)

Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

4
2.0
8

Cambridge Maryland Cottage From $275 per night (USD)

Peaceful Multi-Generational Waterfront Retreat with Pool. No cleaning fees!

Peaceful Multi-Generational Waterfront Retreat with Pool. No cleaning fees!

4
3.0
12

Cambridge Maryland Private vacation home From $750 per night (USD)

Hudson Creek Gorgeous Private Home Awaits your arrival. This place has it all!

Hudson Creek Gorgeous Private Home Awaits your arrival. This place has it all!

7
5.0
15

Cambridge Maryland Private vacation home From $799 per night (USD)

Victorian Home In Historic West End

Victorian Home In Historic West End

6
3.0
13

Cambridge Maryland Private vacation home Click For Pricing

Attractive Waterfront Home over looking Choptank River. Sleeps 5

Attractive Waterfront Home over looking Choptank River. Sleeps 5

3
3.0
7

Cambridge Maryland Private vacation home From $417 per night (USD)

$Waterfront Nature\/Outdoor Lovers Secluded Estate$

Waterfront Nature\/Outdoor Lovers Secluded Estate

5
5.0
14

Taylors Island Maryland Private vacation home From $567 per night (USD)

Waterfront Haven in Cambridge, Md - sleeps 10, 4 bedrooms

Waterfront Haven in Cambridge, Md - sleeps 10, 4 bedrooms

4
2.0
10

Cambridge Maryland Private vacation home From $504 per night (USD)

Quarterdeck at Swan Cove Manor

Quarterdeck at Swan Cove Manor

1
1.0
4

Cambridge Maryland Private vacation home From $254 per night (USD)

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

3
2.0
9

Cambridge Maryland Cottage From $863 per night (USD)

Modernized classic. Historic district near water.

Modernized classic. Historic district near water.

3
3.0
6

Cambridge Maryland Private vacation home From $405 per night (USD)

A Beautiful Waterfront Retreat for Family Gatherings!

A Beautiful Waterfront Retreat for Family Gatherings!

6
4.0
12

Woolford Maryland Private vacation home From $995 per night (USD)

Mariner at Swan Cove Manor

Mariner at Swan Cove Manor

5
4.0
18

Cambridge Maryland Private vacation home From $1280 per night (USD)

Waterfront Vintage Eastern Shore Retreat

Waterfront Vintage Eastern Shore Retreat

5
3.0
10

East New Market Maryland Private vacation home Click For Pricing

House close to Great Marsh Park and Downtown

House close to Great Marsh Park and Downtown

3
2.0
6

Cambridge Maryland Private vacation home From $800 per night (USD)

Outrigger at Swan Cove Manor

Outrigger at Swan Cove Manor

4
3.0
12

Cambridge Maryland Private vacation home From $571 per night (USD)

Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool

Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool

4
5.0
17

Cambridge Maryland Private vacation home From $708 per night (USD)

August 4-7 , 2016 AVAILABLE BOOK NOW!!!

August 4-7 , 2016 AVAILABLE BOOK NOW!!!

1
1.0
4

Fishing Creek Maryland Apartment From $150 per night (USD)

BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!

BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!

4
2.0
10

Fishing Creek Maryland Private vacation home From $260 per night (USD)

Chesapeake Waterfront with Private Beach & Pool

Chesapeake Waterfront with Private Beach & Pool

3
3.0
9

Cambridge Maryland Private vacation home Click For Pricing

Waterfront Family Retreat with Pool on 7+ acres!

Waterfront Family Retreat with Pool on 7+ acres!

10
7.0
24

Woolford Maryland Private vacation home From $1500 per night (USD)

Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD

Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD

3
2.0
10

Cambridge Maryland Private vacation home From $518 per night (USD)

Cottage on Cabin Creek

Cottage on Cabin Creek

1
1.0
2

East New Market Maryland Private vacation home From $250 per night (USD)

$Year Round Waterfront Estate \/ Family Reunions \/ Retreats - Sleeps 28$

Year Round Waterfront Estate \/ Family Reunions \/ Retreats - Sleeps 28

7
7.0
28

Cambridge Maryland Private vacation home From $1700 per night (USD)

The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula

The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula

3
1.0
5

Cambridge Maryland Cottage From $254 per night (USD)

$BayDreams - IronMan\/Eagleman Retreat on the bay$

BayDreams - IronMan\/Eagleman Retreat on the bay

4
3.0
8

Cambridge Maryland Private vacation home From $435 per night (USD)

$CH Waterfront Home w\/ Dock, Pool, Sandy Beach, Kayaks, 5BR\/3.5BA Sleeps up to 16$

CH Waterfront Home w\/ Dock, Pool, Sandy Beach, Kayaks, 5BR\/3.5BA Sleeps up to 16

5
4.0
16

Cambridge Maryland Private vacation home From $1269 per night (USD)

$Weddings\/Reunions\/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate$

Weddings\/Reunions\/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate

20
17.0
60

Cambridge Maryland Private vacation home From $5100 per night (USD)

$Waterfront 5BR\/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18$

Waterfront 5BR\/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18

5
4.0
12

Cambridge Maryland Private vacation home From $1250 per night (USD)

Peaceful Cambridge Home on Jenkins Creek

Peaceful Cambridge Home on Jenkins Creek

3
2.0
6

Cambridge Maryland Private vacation home From $363 per night (USD)

A Vacation Away From It All-Family And Pet Friendly

A Vacation Away From It All-Family And Pet Friendly

5
5.0
12

Taylors Island Maryland Private vacation home From $695 per night (USD)

Private waterfront cottage with pool on Church Creek

Private waterfront cottage with pool on Church Creek

2
1.0
4

Cambridge Maryland Cottage From $212 per night (USD)

Best Kept Secret By the Bay

Best Kept Secret By the Bay

2
2.0
4

Fishing Creek Maryland Private vacation home From $179 per night (USD)

$Private Waterfront Family Retreat w\/ Pool Pickleball Basketball and Volleyball$

Private Waterfront Family Retreat w\/ Pool Pickleball Basketball and Volleyball

4
2.0
14

Taylors Island Maryland Agritourism From $530 per night (USD)

GORGEOUS, WATERFRONT HOME WITH POOL IS PERFECT FOR FAMILIES! WINTER DEALS NOW

GORGEOUS, WATERFRONT HOME WITH POOL IS PERFECT FOR FAMILIES! WINTER DEALS NOW

7
5.0
14

Cambridge Maryland Private vacation home From $632 per night (USD)

Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

5
3.0
10

East New Market Maryland Private vacation home From $698 per night (USD)

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier

8
7.0
22

Cambridge Maryland Private vacation home From $895 per night (USD)

Renovated Historic Waterfront Home with Pool, Dock, 200 acres

Renovated Historic Waterfront Home with Pool, Dock, 200 acres

7
5.0
18

Cambridge Maryland Private vacation home From $845 per night (USD)

Spacious, pet-friendly 3-bedroom home

Spacious, pet-friendly 3-bedroom home

3
1.0
6

Cambridge Maryland Private vacation home From $299 per night (USD)

Remarkable waterfront property on 270 acres

Remarkable waterfront property on 270 acres

5
7.0
15

Cambridge Maryland Agritourism From $1800 per night (USD)

Stylish Victorian in Historic District

Stylish Victorian in Historic District

3
4.0
10

Cambridge Maryland Private vacation home From $307 per night (USD)

Waterfront retreat with heated pool, historic guest house.

Waterfront retreat with heated pool, historic guest house.

5
4.0
15

Cambridge Maryland Private vacation home Click For Pricing

Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Waterfront Retreat < 4 Mi to Dtwn Cambridge!

4
3.0
9

Cambridge Maryland Private vacation home From $406 per night (USD)

High Water Guest House<br>

High Water Guest House<br>

2
1.0
6

Cambridge Maryland Private vacation home From $350 per night (USD)

Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub

Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub

7
7.0
17

Cambridge Maryland Private vacation home From $900 per night (USD)

Beautiful Home in Historic Waterfront District, Walk to Downtown!

Beautiful Home in Historic Waterfront District, Walk to Downtown!

3
2.0
7

Cambridge Maryland Private vacation home From $215 per night (USD)

365-degree waterfront views. Quiet property bordering Blackwater River Refuge.

365-degree waterfront views. Quiet property bordering Blackwater River Refuge.

8
4.0
12

Church Creek Maryland Private vacation home From $599 per night (USD)

$Pristine 5 Acre Home\/Pool\/Pool House$

Pristine 5 Acre Home\/Pool\/Pool House

4
5.0
8

Hurlock Maryland Private vacation home From $499 per night (USD)

Cozy Home in Historic West End Perfect for Ironman

Cozy Home in Historic West End Perfect for Ironman

4
2.0
8

Cambridge Maryland Private vacation home From $295 per night (USD)

Casual Bungalow close to Choptank River, sleeps 5

Casual Bungalow close to Choptank River, sleeps 5

2
1.0
6

Cambridge Maryland Private vacation home Click For Pricing

Nanticoke River Retreat

Nanticoke River Retreat

3
2.0
12

Vienna Maryland Private vacation home From $330 per night (USD)

$Luxe Chesapeake Getaway \/ 3-Bedroom Townhome$

Luxe Chesapeake Getaway \/ 3-Bedroom Townhome

3
3.0
8

Cambridge Maryland Private vacation home From $303 per night (USD)

The Schultz Estate

The Schultz Estate

6
3.0
14

Fishing Creek Maryland Private vacation home From $223 per night (USD)

$New private waterfront Eastern shore home w\/ pier + peaceful water views$

New private waterfront Eastern shore home w\/ pier + peaceful water views

3
2.0
10

Cambridge Maryland Private vacation home From $365 per night (USD)

A little slice of heaven on the Choptank River

A little slice of heaven on the Choptank River

2
2.0
6

East New Market Maryland Lodge From $325 per night (USD)

Waterfront Hoopers Island Light House Point Vacation Rental Sunsets pet friendly

Waterfront Hoopers Island Light House Point Vacation Rental Sunsets pet friendly

4
3.0
12

Fishing Creek Maryland Private vacation home Click For Pricing

Casa Maria heart of downtown Cambridge Maryland

Casa Maria heart of downtown Cambridge Maryland

1
1.0
2

Cambridge Maryland Apartment From $142 per night (USD)

New Waterfront! Drop Anchor on Brannocks Bay. An Amazing waterfront retreat!

New Waterfront! Drop Anchor on Brannocks Bay. An Amazing waterfront retreat!

3
3.0
8

Cambridge Maryland Private vacation home From $346 per night (USD)

Historic Farmhouse on the Chesapeake Bay! PANORAMIC Waterfront Sunsets. 🌅

Historic Farmhouse on the Chesapeake Bay! PANORAMIC Waterfront Sunsets. 🌅

3
2.0
10

Cambridge Maryland Agritourism Click For Pricing

New listing! Riverside Retreat on the Choptank River

New listing! Riverside Retreat on the Choptank River

3
2.0
6

Cambridge Maryland Private vacation home From $250 per night (USD)

Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

5
3.0
10

East New Market Maryland Private vacation home From $550 per night (USD)

Magnificent Historic Home by Water is Ready!

Magnificent Historic Home by Water is Ready!

5
4.0
9

Cambridge Maryland Private vacation home From $499 per night (USD)

$Cambridge Beach Home on Choptank River w\/ Pier!$

Cambridge Beach Home on Choptank River w\/ Pier!

5
3.0
12

Cambridge Maryland Private vacation home From $567 per night (USD)

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