Short-Term Rentals in Woolford, MD: Compare 10+ Sites & Save

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30 Best Short-Term Rentals in Woolford (Starting from $172)

Chesapeake Waterfront - 7BR 5BA - Beach Pool Dock
Chesapeake Waterfront - 7BR 5BA - Beach Pool Dock
House
Woolford, MD, USA
5.8k from Woolford center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach

7 Bedrooms18 Guests
New to Booking
$908
Average price / night
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The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
House
Woolford, MD, 21677, United States
2.0k from Woolford center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms18 Guests
9.6

Exceptional

28 reviews

$538
Average price / night
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Bayfront Gem with Amazing Water Views and Pond!
Bayfront Gem with Amazing Water Views and Pond!
House
MD, USA
6.9k from Woolford center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$580
Average price / night
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Waterfront Getaway with Dock
Waterfront Getaway with Dock
House
Woolford, MD, 21677, United States
2.4k from Woolford center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

54 reviews

$265
Average price / night
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Sunset Breezes - quiet waterfront retreat
Sunset Breezes - quiet waterfront retreat
House
Woolford, MD, USA
9.8k from Woolford center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$246
Average price / night
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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!
Cottage
Cambridge, MD, 21613, United States
2.6k from Woolford center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms9 Guests
10.0

Exceptional

88 reviews

$1090
Average price / night
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2BR Riverfront Retreat on 61 acres with 270 degrees of waterfront/ private Pool
2BR Riverfront Retreat on 61 acres with 270 degrees of waterfront/ private Pool
House
Cambridge, MD, 21613, United States
3.6k from Woolford center

AC, Dryer, Heater, Internet, Laundry, Living Area, No Smoking, Washer

2 Bedrooms6 Guests
New to Booking
$256
Average price / night
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Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!
House
Madison, MD, 21648, United States
4.0k from Woolford center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$331
Average price / night
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Waterfront Family Retreat with Pool on 7+ acres!
Waterfront Family Retreat with Pool on 7+ acres!
House
Woolford, MD, 21677, United States
5.3k from Woolford center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

10 Bedrooms24 Guests
10.0

Exceptional

63 reviews

$1626
Average price / night
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Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub
Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub
House
Cambridge, MD, 21613, United States
5.3k from Woolford center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

8 Bedrooms17 Guests
9.4

Superb

6 reviews

$1434
Average price / night
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Private 2 Acre Waterfront Family Retreat with Pool & Pier
Private 2 Acre Waterfront Family Retreat with Pool & Pier
House
Cambridge, MD, 21613, United States
5.7k from Woolford center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

8 Bedrooms22 Guests
9.6

Exceptional

89 reviews

$1123
Average price / night
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 Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
House
Woolford, MD, 21677, United States
5.8k from Woolford center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

7 Bedrooms18 Guests
9.8

Exceptional

75 reviews

$1164
Average price / night
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\"Endless Summer\" Waterfront on the Chesapeake Bay!
\"Endless Summer\" Waterfront on the Chesapeake Bay!
House
Woolford, MD, 21677, United States
6.1k from Woolford center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms12 Guests
10.0

Exceptional

6 reviews

$759
Average price / night
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Peaceful family get away with in ground pool close to town
Peaceful family get away with in ground pool close to town
House
Cambridge, MD, 21613, United States
6.2k from Woolford center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

4 Bedrooms14 Guests
10.0

Exceptional

39 reviews

$662
Average price / night
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Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22
Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22
House
Cambridge, MD, 21613, United States
6.8k from Woolford center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Laundry, Microwave, No Smoking

8 Bedrooms28 Guests
New to Booking
$1964
Average price / night
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Bayfront Gem w/ Amazing Water Views + Pond!
Bayfront Gem w/ Amazing Water Views + Pond!
House
Madison, MD, 21648-1103, United States
6.9k from Woolford center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms10 Guests
10.0

Exceptional

19 reviews

$509
Average price / night
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365-degree waterfront views. Quiet property bordering Blackwater River Refuge.
365-degree waterfront views. Quiet property bordering Blackwater River Refuge.
House
Church Creek, MD, 21622, United States
7.7k from Woolford center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

8 Bedrooms13 Guests
10.0

Exceptional

5 reviews

$511
Average price / night
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Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room
Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room
House
Cambridge, MD, 21613, United States
7.8k from Woolford center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
10.0

Exceptional

70 reviews

$749
Average price / night
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Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
House
Cambridge, MD, 21613, United States
8.5k from Woolford center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
9.4

Superb

6 reviews

$397
Average price / night
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Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16
Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16
House
Cambridge, MD, 21613, United States
8.8k from Woolford center

AC, Barbecue, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms16 Guests
9.4

Superb

15 reviews

$1425
Average price / night
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 Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate
Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate
House
Cambridge, MD, 21613, United States
8.9k from Woolford center

AC, Arcade, Barbecue, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Internet

20 Bedrooms70 Guests
10.0

Exceptional

2 reviews

$6937
Average price / night
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Waterfront Home with Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 20
Waterfront Home with Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 20
House
Cambridge, MD, 21613, United States
8.9k from Woolford center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms18 Guests
6.4

Good

5 reviews

$1443
Average price / night
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Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 14
Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 14
House
Cambridge, MD, 21613, United States
9.0k from Woolford center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

6 Bedrooms12 Guests
9.6

Exceptional

4 reviews

$1443
Average price / night
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 Relaxing getaway at Outrigger w/ plenty of space sleeping up to 21
Relaxing getaway at Outrigger w/ plenty of space sleeping up to 21
House
Cambridge, MD, 21613, United States
9.0k from Woolford center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms12 Guests
9.0

Fabulous

15 reviews

$610
Average price / night
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Quarterdeck cottage at Swan Cove Manor - A cozy stay for up to 4 people
Quarterdeck cottage at Swan Cove Manor - A cozy stay for up to 4 people
House
Cambridge, MD, 21613, United States
9.0k from Woolford center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

8 reviews

$240
Average price / night
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Waterfront Getaway for Two
Waterfront Getaway for Two
Apartment
Cambridge, MD, 21613, United States
9.2k from Woolford center

AC, Fireplace, Heater, Internet, Kitchen, No Smoking, Outdoor Grill, Patio

1 Bedroom2 Guests
New to Booking
$172
Average price / night
Check Availability
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
House
Cambridge, MD, 21613, United States
9.7k from Woolford center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms16 Guests
9.8

Exceptional

29 reviews

$795
Average price / night
Check Availability

Other accommodation types in Woolford:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Woolford.

Stay Near Woolford's Top Attractions

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Woolford Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 30 verified short-term rentals in Woolford, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Woolford vary depending on location, property size, and travel dates. Rates typically start from around $172 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Woolford include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Woolford, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Woolford often include amenities such as Fireplace/Heating, Bedding/Linens, and Wellness Facilities, providing a comfortable and convenient stay.

Short-term rentals in Woolford are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.