The Best Vacation Rentals - Vacation Rentals in Woolford

Multi-Generational Waterfront Retreat with Pool! From US $833
         

10.0 (70 Reviews)
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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, Pets, Dock From US $874
         

9.8 (75 Reviews)
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  • Pet Friendly
Family and Pet-Friendly, Waterfront with Pier From US $275
         

10.0 (265 Reviews)
Cottage
  • Air Conditioner
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  • Pet Friendly
Year Round Waterfront Estate/Family Reunions/Retreats - Sleeps 28 From US $1,287
         

Waterfront Getaway with Dock From US $219
         

10.0 (51 Reviews)
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  • Pet Friendly
Sunset Breezes - quiet waterfront retreat From US $313
         

10.0 (41 Reviews)
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  • TV

Luxury Places to Stay in Woolford

Over 37+ Luxury Places to Stay in or Near Woolford
Waterfront Family Retreat with Pool on 7+ acres! From US $1,618
         

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

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Mariner at Swan Cove Manor From US $1,296
         

6.4 (5 Reviews)
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Woolford

Over 13+ Top-Rated Vacation Rentals with a Pool in or Near Woolford
A Vacation Away From It All-Family And Pet Friendly From US $885
         

A Beautiful Waterfront Retreat for Family Gatherings! From US $980
         

10.0 (23 Reviews)
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  • Air Conditioner
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  • Pet Friendly
"Endless Summer" Waterfront on the Chesapeake Bay! From US $628
         

10.0 (5 Reviews)
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  • Pet Friendly
Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool From US $820
         

Outrigger at Swan Cove Manor From US $426
         

9.0 (15 Reviews)
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  • Air Conditioner
  • Parking
  • Pet Friendly
Chesapeake Waterfront - 7BR 5BA - Beach Pool Dock From US $909
         

Pet-Friendly Vacation Rentals in Woolford

Over 9+ Pet-Friendly Vacation Rentals in or Near Woolford
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks From US $473
         

Quarterdeck at Swan Cove Manor From US $215
         

10.0 (8 Reviews)
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  • Pet Friendly
Waterfront Getaway for Two From US $164
         

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  • Pet Friendly
  • Balcony/Terrace
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
         

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

Large Vacation Homes & Villas in Woolford

Over 5+ Large Vacation Homes & Villas in or Near Woolford
Bayfront Gem w/Amazing Water Views + Pond! From US $571
         

10.0 (19 Reviews)
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  • Air Conditioner
  • Parking
  • TV
Magnificent Madison's private bay getaway home! From US $438
         

Woolford Varoom and Airbnb Places to Stay Under $200

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

Instantly Bookable Vacation Homes in Woolford

Over 1+ Instantly Bookable Vacation Homes in or Near Woolford
Chesapeake Sunset Cottage From US $452
         

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About Woolford Vacation Rentals

With more than 46 Woolford vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Thebestvacationrentals 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 Thebestvacationrentals 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 2323.74 ft² on average, with prices averaging $887 a night.

Thebestvacationrentals 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 39
Cottages 3
Holiday Apartments 2
Cabin Rentals 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Woolford

Pro Tip: Thebestvacationrentals makes it easy to compare the best listings on Thebestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Thebestvacationrentals 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