Women In Travel - Vacation Rentals in Woolford

Bayfront Gem with Amazing Water Views and Pond! From US $580
         

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10.0 (2 Reviews)
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Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted From US $1,164
         

Family and Pet-Friendly, Waterfront with Pier From US $333
         

10.0 (265 Reviews)
Cottage
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  • Pet Friendly
Waterfront Getaway with Dock From US $265
         

10.0 (54 Reviews)
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  • Pet Friendly
Sunset Breezes - quiet waterfront retreat From US $356
         

10.0 (43 Reviews)
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  • TV

Luxury Places to Stay in Woolford

Over 41+ Luxury Places to Stay in or Near Woolford
Waterfront Family Retreat with Pool on 7+ acres! From US $1,626
         

10.0 (63 Reviews)
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Bayberry Cove From US $1,616
         

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Top-Rated Vacation Rentals with a Pool in Woolford

Over 16+ Top-Rated Vacation Rentals with a Pool in or Near Woolford
A Vacation Away From It All-Family And Pet Friendly From US $885
         

"Endless Summer" Waterfront on the Chesapeake Bay! From US $750
         

10.0 (6 Reviews)
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Private 2 Acre Waterfront Family Retreat with Pool & Pier From US $1,123
         

9.6 (89 Reviews)
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  • Pet Friendly
Relaxing getaway at Outrigger w/plenty of space sleeping up to 21 From US $629
         

Chesapeake Waterfront - 7BR 5BA - Beach Pool Dock From US $909
         

Pet-Friendly Vacation Rentals in Woolford

Over 12+ Pet-Friendly Vacation Rentals in or Near Woolford
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks From US $405
         

Waterfront Getaway for Two From US $154
         

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  • Pet Friendly
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Bay Views & Fire Pit: Taylor’s Island Retreat From US $515
         

10.0 (12 Reviews)
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  • Pet Friendly
The Retreat - The Perfect Ambiance! From US $417
         

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  • Pet Friendly
  • Pool
See More Pet-Friendly Vacation Rentals in Woolford on PetFriendly.io

Large Vacation Homes & Villas in Woolford

Over 6+ Large Vacation Homes & Villas in or Near Woolford
Eastern Shore Group Getaway! Riverfront Home From US $752
         

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Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool From US $962
         

Magnificent Madison's private bay getaway home! From US $438
         

Woolford Vacation Rentals and Airbnb Places to Stay Under $200

Over 1+ Woolford Vacation Rentals and Airbnb Places to Stay Under $200

Instantly Bookable Vacation Homes in Woolford

Over 2+ Instantly Bookable Vacation Homes in or Near Woolford
Private waterfront cottage with pool on Church Creek From US $251
         

10.0 (62 Reviews)
Cottage
  • Air Conditioner
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  • Pool
Chesapeake Sunset Cottage From US $452
         

New
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About Woolford Vacation Rentals

With more than 50 Woolford vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Womenintravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Woolford.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Womenintravel Woolford, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Woolford. Places to stay near Woolford are 2217.92 ft² on average, with prices averaging $952 a night.

Womenintravel makes it easy and safe to find and compare vacation rentals in Woolford with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Woolford

Type Count
Vacation Homes 42
Cottages 3
Holiday Apartments 2
Others 2
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Woolford

Pro Tip: Womenintravel makes it easy to compare the best listings on Womenintravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Womenintravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Woolford.

Weather in Woolford

View the weather forecast for Woolford before booking your Woolford Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Woolford Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Woolford?
How many vacation rentals are available in Woolford?

Currently, the total number of properties listed in 2026 is over 50 in the Woolford area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Woolford.