1+ Vacation Rentals Near Madison |
  1. USA
  2. Maryland
  3. Madison

Wyknot Cabin - Vacation Rentals in Madison

A Vacation Away From It All-Family And Pet Friendly in Taylors Island From US $1,100
         

10.0 (61 Reviews)
Cabin
A Vacation Away From It All-Family And Pet Friendly
  • Air Conditioner
  • Parking
  • Pool

View Availability
See More Madison Vacation Rentals

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 in Cambridge From US $8,121
         

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

View Availability
Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22 in Cambridge From US $2,257
         

8.0 (1 Review)
House
Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22
  • Air Conditioner
  • Parking
  • Pool

View Availability
Remarkable waterfront property on 270 acres in Cambridge From US $2,007
         

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

View Availability
Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub in Cambridge From US $1,889
         

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

View Availability
4-bedroom historic waterfront farmhouse with pool in Cambridge in Cambridge From US $1,863
         

10.0 (1 Review)
Other
4-bedroom historic waterfront farmhouse with pool in Cambridge
  • Air Conditioner
  • Parking
  • Pool

View Availability
Waterfront Family Retreat with Pool on 7+ acres! in Woolford From US $1,838
         

10.0 (66 Reviews)
House
Waterfront Family Retreat with Pool on 7+ acres!
  • Air Conditioner
  • Parking
  • Pool

View Availability
Eagles Nest. Discover Tranquility, Privacy, Excellence, and so much more. in Cambridge From US $1,836
         

10.0 (2 Reviews)
House
Eagles Nest. Discover Tranquility, Privacy, Excellence, and so much more.
  • Air Conditioner
  • Parking
  • TV

View Availability
Waterfront Home with Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 20 in Cambridge From US $1,702
         

6.4 (5 Reviews)
House
Waterfront Home with Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 20
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
See More Madison Luxury Vacation Rentals
Find More Madison Villas, Resorts, & Rentals on BedroomVillas

Top-Rated Vacation Rentals with a Pool in Madison

Over 20+ Top-Rated Vacation Rentals with a Pool in or Near Madison
Peaceful family get away with in ground pool close to town in Cambridge From US $828
         

10.0 (42 Reviews)
House
Peaceful family get away with in ground pool close to town
  • Air Conditioner
  • Parking
  • Pool

View Availability
Rippling Waters on Fishing Creek in Cambridge From US $996
         

10.0 (4 Reviews)
House
Rippling Waters on Fishing Creek
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Private Waterfront Family Retreat w/Pier Pool Pickleball Basketball Volleyball in Taylors Island From US $767
         

9.8 (90 Reviews)
House
Private Waterfront Family Retreat w/Pier Pool Pickleball Basketball Volleyball
  • Air Conditioner
  • Parking
  • Pool

View Availability
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted in Woolford From US $1,129
         

9.8 (79 Reviews)
House
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals in Cambridge From US $807
         

9.8 (35 Reviews)
House
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
  • Air Conditioner
  • Parking
  • Pool

View Availability
"Endless Summer" Waterfront on the Chesapeake Bay! in Woolford From US $1,070
         

9.8 (12 Reviews)
House
"Endless Summer" Waterfront on the Chesapeake Bay!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou in Cambridge From US $1,371
         

9.4 (6 Reviews)
House
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Relaxing getaway at Outrigger w/plenty of space sleeping up to 21 in Cambridge From US $560
         

9.0 (16 Reviews)
House
Relaxing getaway at Outrigger w/plenty of space sleeping up to 21
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
See More Madison Vacation Rentals with a Pool

Pet-Friendly Vacation Rentals in Madison

Over 22+ Pet-Friendly Vacation Rentals in or Near Madison
Waterfront Getaway with Dock in Woolford From US $278
         

10.0 (64 Reviews)
House
Waterfront Getaway with Dock
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Chesapeake Waterfront - 7BR 5BA - Beach Pool Dock in Woolford From US $909
         

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

View Availability
About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger! in Taylors Island From US $757
         

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

View Availability
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks in Woolford From US $650
         

9.6 (34 Reviews)
House
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate. in Cambridge From US $529
         

9.6 (8 Reviews)
House
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Waterfront Fishing Creek Cottage with Guesthouse Pier-Kayaks-Fire Pit in Woolford From US $559
         

New
Cottage
Waterfront Fishing Creek Cottage with Guesthouse Pier-Kayaks-Fire Pit
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Quarterdeck cottage at Swan Cove Manor - A cozy stay for up to 4 people in Cambridge From US $376
         

10.0 (9 Reviews)
House
Quarterdeck cottage at Swan Cove Manor - A cozy stay for up to 4 people
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
About Time-Main House in Taylors Island From US $438
         

10.0 (5 Reviews)
House
About Time-Main House
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
See More Pet-Friendly Vacation Rentals in Madison on PetFriendly.io

Large Vacation Homes & Villas in Madison

Over 14+ Large Vacation Homes & Villas in or Near Madison
Bayfront Gem w/Amazing Water Views + Pond! in Madison From US $722
         

10.0 (20 Reviews)
House
Bayfront Gem w/Amazing Water Views + Pond!
  • Air Conditioner
  • Parking
  • TV

View Availability
Bayfront Gem w/Amazing Water Views + Pond! in Madison From US $557
         

|
10.0 (2 Reviews)
House
Bayfront Gem w/Amazing Water Views + Pond!
  • Parking
  • Security/Safety
  • Sports/Activities

View Availability
Private 9 acre Family Retreat on the Chesapeake Bay in Cambridge From US $775
         

10.0 (16 Reviews)
House
Private 9 acre Family Retreat on the Chesapeake Bay
  • Air Conditioner
  • Parking
  • TV

View Availability
365-degree waterfront views. Quiet property bordering Blackwater River Refuge. in Church Creek From US $685
         

10.0 (7 Reviews)
House
365-degree waterfront views. Quiet property bordering Blackwater River Refuge.
  • Air Conditioner
  • Parking
  • TV

View Availability
Waterfront Nature/Outdoor Lovers Secluded Estate in Taylors Island From US $681
         

10.0 (30 Reviews)
House
Waterfront Nature/Outdoor Lovers Secluded Estate
  • Air Conditioner
  • Parking
  • TV

View Availability
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier! in Madison From US $342
         

10.0 (14 Reviews)
House
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!
  • Air Conditioner
  • Parking
  • TV

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

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

View Availability
Tidal Serenity- Remote Waterfront Home with dock in Taylors Island From US $378
         

10.0 (15 Reviews)
House
Tidal Serenity- Remote Waterfront Home with dock
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

View Availability
See More Family Vacation Rentals in Madison on FVR

Madison Vacation Rentals and Airbnb Places to Stay Under $200

Over 1+ Madison Vacation Rentals and Airbnb Places to Stay Under $200
Farmhouse Charm Woolford Studio Apt. w/Amazing Eastern Shore Sunrise & Sunsetsn in Woolford From US $177
         

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

View Availability
See More Madison Vacation Rental Deals

Instantly Bookable Vacation Homes in Madison

Over 8+ Instantly Bookable Vacation Homes in or Near Madison
Sunset Breezes - quiet waterfront retreat in Dorchester County From US $491
         

10.0 (45 Reviews)
House
Sunset Breezes - quiet waterfront retreat
  • Air Conditioner
  • Parking
  • TV

View Availability
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach! in Cambridge From US $1,090
         

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

View Availability
Private waterfront cottage with pool on Church Creek in Cambridge From US $251
         

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

View Availability
Bay Views & Fire Pit: Taylor’s Island Retreat in Taylors Island From US $515
         

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

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

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

View Availability
Eastern Shore Group Getaway! Riverfront Home in Church Creek From US $645
         

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

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

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

View Availability
The Retreat - The Perfect Ambiance! in Woolford From US $417
         

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

View Availability
See More Madison Short-Term Vacation Rentals

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 US $1,100 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

Madison Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Madison?

There are a lot of options in Madison. If you plan on staying in the Madison area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Madison:

How many vacation rentals are available in Madison?

Currently, the total number of properties listed in 2026 is over 1 in the Madison area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Madison.