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Wyknot Cabin - Vacation Rentals in Madison

A Vacation Away From It All-Family And Pet Friendly From US $885
         

10.0 (60 Reviews)
Cabin
A Vacation Away From It All-Family And Pet Friendly
  • Air Conditioner
  • Parking
  • Pool

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Luxury Places to Stay in Madison

Over 54+ Luxury Places to Stay in or Near Madison
Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate From US $6,232
         

10.0 (2 Reviews)
House
Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate
  • Air Conditioner
  • Parking
  • Pool

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Remarkable waterfront property on 270 acres From US $1,938
         

New
Other
Remarkable waterfront property on 270 acres
  • Air Conditioner
  • Parking
  • Pool

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Bayberry Cove From US $1,616
         

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New
House
Bayberry Cove
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Family Retreat with Pool on 7+ acres! From US $1,493
         

10.0 (63 Reviews)
House
Waterfront Family Retreat with Pool on 7+ acres!
  • Air Conditioner
  • Parking
  • Pool

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Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub From US $1,328
         

9.4 (6 Reviews)
House
Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub
  • Air Conditioner
  • Parking
  • Pet Friendly

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Mariner at Swan Cove Manor From US $1,296
         

6.4 (5 Reviews)
House
Mariner at Swan Cove Manor
  • Air Conditioner
  • Parking
  • Pet Friendly

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CH Waterfront Home w/Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16 From US $1,296
         

9.4 (15 Reviews)
House
CH Waterfront Home w/Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18 From US $1,296
         

9.6 (4 Reviews)
House
Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18
  • Air Conditioner
  • Parking
  • Pet Friendly

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Top-Rated Vacation Rentals with a Pool in Madison

Over 20+ Top-Rated Vacation Rentals with a Pool in or Near Madison
Family and Pet-Friendly, Waterfront with Pier From US $275
         

10.0 (265 Reviews)
Cottage
Family and Pet-Friendly, Waterfront with Pier
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach! From US $1,095
         

10.0 (88 Reviews)
Cottage
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Peaceful family get away with in ground pool and hot tub close to town From US $514
         

10.0 (38 Reviews)
House
Peaceful family get away with in ground pool and hot tub close to town
  • Air Conditioner
  • Parking
  • Pool

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"Endless Summer" Waterfront on the Chesapeake Bay! From US $707
         

10.0 (6 Reviews)
House
"Endless Summer" Waterfront on the Chesapeake Bay!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Private Waterfront Family Retreat w/Pier Pool Pickleball Basketball Volleyball From US $618
         

9.8 (85 Reviews)
Other
Private Waterfront Family Retreat w/Pier Pool Pickleball Basketball Volleyball
  • Air Conditioner
  • Parking
  • Pool

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Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock From US $957
         

9.8 (75 Reviews)
House
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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

9.8 (74 Reviews)
House
Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals From US $795
         

9.8 (29 Reviews)
House
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Madison

Over 21+ Pet-Friendly Vacation Rentals in or Near Madison
Waterfront Getaway with Dock From US $279
         

10.0 (52 Reviews)
House
Waterfront Getaway with Dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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

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New
House
Chesapeake Waterfront - 7BR 5BA - Beach Pool Dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger! From US $555
         

10.0 (5 Reviews)
House
About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger!
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks From US $512
         

9.4 (25 Reviews)
House
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
  • Air Conditioner
  • Parking
  • Pet Friendly

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Fish, kayak, bike, and more at this private serene 24-acre waterfront estate. From US $397
         

9.4 (6 Reviews)
House
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou From US $1,023
         

9.2 (5 Reviews)
House
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
  • Air Conditioner
  • Parking
  • Pet Friendly

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2BR Riverfront Retreat on 61 acres with 270 degrees of waterfront/private Pool From US $208
         

New
House
2BR Riverfront Retreat on 61 acres with 270 degrees of waterfront/private Pool
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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Outrigger at Swan Cove Manor From US $427
         

9.0 (15 Reviews)
House
Outrigger at Swan Cove Manor
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Madison

Over 15+ Large Vacation Homes & Villas in or Near Madison
Bayfront Gem w/Amazing Water Views + Pond! From US $577
         

10.0 (19 Reviews)
House
Bayfront Gem w/Amazing Water Views + Pond!
  • Air Conditioner
  • Parking
  • TV

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

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10.0 (2 Reviews)
House
Bayfront Gem with Amazing Water Views and Pond!
  • Parking
  • Accessibility
  • Security/Safety

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Private 9 acre Family Retreat on the Chesapeake Bay From US $674
         

10.0 (13 Reviews)
House
Private 9 acre Family Retreat on the Chesapeake Bay
  • Air Conditioner
  • Parking
  • TV

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Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier! From US $265
         

10.0 (11 Reviews)
House
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!
  • Air Conditioner
  • Parking
  • TV

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Eastern Shore Group Getaway! Riverfront Home From US $645
         

New
House
Eastern Shore Group Getaway! Riverfront Home
  • Air Conditioner
  • Parking
  • TV

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Waterfront Nature/Outdoor Lovers Secluded Estate From US $606
         

10.0 (26 Reviews)
House
Waterfront Nature/Outdoor Lovers Secluded Estate
  • Air Conditioner
  • Parking
  • TV

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About Time-Bunkhouse Only From US $259
         

10.0 (2 Reviews)
House
About Time-Bunkhouse Only
  • Air Conditioner
  • Parking
  • Pet Friendly

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Year Round Waterfront Estate/Family Reunions/Retreats - Sleeps 28 From US $1,307
         

10.0 (81 Reviews)
House
Year Round Waterfront Estate/Family Reunions/Retreats - Sleeps 28
  • Air Conditioner
  • Parking
  • Pet Friendly

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Madison Varoom and Airbnb Places to Stay Under $200

Over 2+ Madison Varoom and Airbnb Places to Stay Under $200
Waterfront Getaway for Two From US $164
         

New
Apartment
Waterfront Getaway for Two
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

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Farmhouse Charm Woolford Studio Apt. w/Amazing Eastern Shore Sunrise & Sunsetsn From US $177
         

10.0 (3 Reviews)
Apartment
Farmhouse Charm Woolford Studio Apt. w/Amazing Eastern Shore Sunrise & Sunsetsn
  • Air Conditioner
  • Parking
  • TV

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Instantly Bookable Vacation Homes in Madison

Over 8+ Instantly Bookable Vacation Homes in or Near Madison
Sunset Breezes - quiet waterfront retreat From US $313
         

10.0 (41 Reviews)
House
Sunset Breezes - quiet waterfront retreat
  • Air Conditioner
  • Parking
  • TV

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Private waterfront cottage with pool on Church Creek From US $251
         

10.0 (62 Reviews)
Cottage
Private waterfront cottage with pool on Church Creek
  • Air Conditioner
  • Parking
  • Pool

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

10.0 (12 Reviews)
House
Bay Views & Fire Pit: Taylor’s Island Retreat
  • Air Conditioner
  • Parking
  • Pet Friendly

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365-degree waterfront views. Quiet property bordering Blackwater River Refuge. From US $512
         

10.0 (5 Reviews)
House
365-degree waterfront views. Quiet property bordering Blackwater River Refuge.
  • Air Conditioner
  • Parking
  • TV

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Willoughby - Over 10,000 SqFt, Indoor Pool, Grill, Sleeps 24! From US $1,130
         

4.2 (6 Reviews)
House
Willoughby - Over 10,000 SqFt, Indoor Pool, Grill, Sleeps 24!
  • Air Conditioner
  • Pet Friendly
  • Pool

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Short drive to Downtown Cambridge | Indoor Pool | Private Dock | Kayaks | Pet Fr From US $904
         

New
House
Short drive to Downtown Cambridge | Indoor Pool | Private Dock | Kayaks | Pet Fr
  • Air Conditioner
  • Parking
  • Pet Friendly

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Chesapeake Bay Waterfront Retreat. Access to Private Dock, Beach and Pool. From US $500
         

New
House
Chesapeake Bay Waterfront Retreat. Access to Private Dock, Beach and Pool.
  • Air Conditioner
  • Pet Friendly
  • Pool

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The Retreat - The Perfect Ambiance! From US $417
         

New
House
The Retreat - The Perfect Ambiance!
  • Air Conditioner
  • Pet Friendly
  • Pool

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About Madison Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Wyknotcabin Madison, 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 Madison. Places to stay near Madison are 4800 ft² on average, with prices averaging $885 a night.

Wyknotcabin makes it easy and safe to find and compare vacation rentals in Madison 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 Madison

Type Count
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Madison

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

Weather in Madison

View the weather forecast for Madison before booking your Madison 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

Top Attractions Around Madison, MD

Wyknotcabin offers a large selection of top attractions around Madison. Research things to do on your vacation before you visit Madison.


Patuxent River Naval Air Station Calvert Cliffs State Park St. Michaels Winery Great Marsh Park Chesapeake Bay Maritime Museum Blackwater National Wildlife Refuge Harriet Tubman Museum and Educational Center Oxford Museum Breezy Point Beach Cove Point Lighthouse Running Hare Vineyard Harriet Tubman Underground Railroad National Historical Park Patuxent River Naval Air Museum Long Wharf Park Sotterley Plantation Layton's Chance Vineyard and Winery Bay Country Shop Perigeaux Vineyards and Winery Bill Burton Fishing Pier State Park Jefferson Patterson Park and Museum