Coastal Cottages for Fall

by Casey Higgins | Posted: Oct 19, 2012 | Updated: Apr 16, 2018

Comments: 1 Comment

Fall is a great time to escape to Virginia’s shores. The crowds are gone, the air is crisp and the coast is as beautiful as summer.

Clear your mind any weekend this fall with a cottage rental in Virginia Beach, on the Eastern Shore or along the Chesapeake Bay.


Atlantic Breeze is a luxurious four-story town home just a quick 3 1/2 block walk to the oceanfront, Boardwalk, dining, shops, live entertainment, and more. Sleeps up to 12.

The Dunes is a sweet cottage just two blocks from the center of the Virginia Beach Boardwalk. A comfortable four-bedroom, fully equipped home with all the amenities for a relaxing beach vacation, The Dunes sleeps up to 10 people.

Matchotank Country Home

Matchotank Country Home

Matchotank Country Home is an expansive place on 50 acres in Onancock. The home sits waterfront with a dock, boat ramp, stocked freshwater pond, and all of the equipment you need to have a great time outdoors. Sleeps 10.

Eagle’s View is a four-bedroom waterfront home near Assateague Lighthouse on Chincoteague Island. It’s a dream destination for outdoor enthusiasts! Soak in the midst of the Wildlife Refuge with over 300 species of birds and wild ponies. The property has a private dock for your use, as well as two master suites – great for multi-generation vacationing. Sleeps 11.

Nestled along the shores of the Chesapeake Bay is Big Bay in White Stone, a comfortable four-bedroom, two bath home with private beach and plenty of recreational opportunities to entertain you in any season. Pull out a kayak and paddle at sunrise with the dolphins or set a few crab pots and pull in a couple of blues for dinner. Sleeps 8-10.

In Grimstead, Gwynn’s Island Cottage overlooks several bodies of water with easy access to the Chesapeake Bay and a private beach. Sleeps 3.

The view from Grandview on the Bay

The view from Grandview on the Bay

The Crab Shack at Grandview in Mathews overlooks the East River. It’s a brand new accommodation with a rooftop deck and gourmet kitchen. You just might want to stay a while longer. Sleeps two comfortably, but air mattresses are available for additional guests. Dog-friendly.

More great coastal cottages, cabins, and vacation rentals:

  • Spinnaker Waterfront – Chincoteague Island: Four-level design with 4 Bedrooms – 4 Baths on three different levels for privacy. Relax and enjoy Four Sun Decks; screened in porch. Waterfront Outdoor Living Area with seating and grill and private boat dock.\
  • Lillenhamn – Mathews: Gorgeous, serene water view from private deck overlooking Woodas Creek. Accommodations for four. Use of kayak and canoe at waters edge.
  • Gibson Cottage – Horn Harbor: Come and relax at this newly renovated 2 bedroom, 2 bath Cottage over looking the Chesapeake Bay. Located at the end of of a public road, quiet neighborhood with lots of room for the kids. Private pier & boat slip for sun bathing or boating
  • The Oyster Farm – Cape Charles: Kings Creek Vacation Rentals
  • Yorktown’s Charming Battlefield Cottage – Yorktown:  Formerly the studio of renowned folk artist Nancy Thomas this recently renovated cottage is located in a quiet and scenic neighborhood on the Yorktown Battlefield on a bluff just above the York River.

Discover more coastal cottages at


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Looking for a log cabin rental. Near mountains.