Winter Getaways

Our waterfront cottages and homes offer the perfect spot to enjoy a quiet winter break or a long weekend. Take in the wide open winter views, cozy interiors and updated kitchens for simmering a pot of chili or crab soup. Many also have fireplaces, hot tubs and are pet friendly!

Sort by:
Starting at (USD)

$425.00

Back Street Cottage
Easton, MD
  • 6 Guests
  • 3 Bedrooms
  • 1.5 Bathrooms
  • Code: Back Street Cottage
  • Pets Allowed
View Rental
Starting at (USD)

$481.00

Carpenter Alley Cottage
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Carpenter Alley
  • Pets Allowed
View Rental
Starting at (USD)

$355.00

Caulk's Cove
Bozman, MD
  • 7 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Caulks Cove
  • Pets Allowed
View Rental
Starting at (USD)

$455.00

Chesapeake Pines
Royal Oak, MD
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Chesapeake Pines
  • Pets Allowed
View Rental
Starting at (USD)

$575.00

Grace Cottage
Oxford, MD
  • 10 Guests
  • 5 Bedrooms
  • 4 Bathrooms
  • Code: Grace Cottage At Sullivan`s Way
View Rental
Starting at (USD)

$430.00

Mallard Point Cottage
McDaniel, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallard Point Cottage
  • Pets Allowed
View Rental
Starting at (USD)

$305.00

Memory Lane
Oxford, MD
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Memory Lane
  • Pets Allowed
View Rental
Starting at (USD)

$335.00

Simplicity Cottage
Tilghman Island, MD
  • 4 Guests
  • 2 Bedrooms
  • 1.5 Bathrooms
  • Code: Simplicity Cottage
  • Pets Allowed
View Rental
Starting at (USD)

$1,215.00

Willoughby
Cambridge, MD
  • 24 Guests
  • 7 Bedrooms
  • 6 Bathrooms
  • Code: Willoughby
  • Pets Allowed
View Rental