Find the best place to stay — Chester

Where to stay around Chester, MD?

Our 2018 property listings offer a large selection of 156 vacation rentals near Chester. From 97 houses to 24 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chester for a holiday or a weekend are on VRBO.

What is the best area to stay when traveling to Chester?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chester:

  • Bay Ridge: 29 vacation rentals
  • Eastport: 160 vacation rentals
  • Historic District: 191 vacation rentals
  • Epping Forest: 19 vacation rentals
  • Winchester-on-the-Severn: 17 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Chester?

VRBO offers a large selection of vacation rentals near lovely places in Chester. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Chesapeake Bay Bridge: 579 vacation rentals
  • Sandy Point State Park: 566 vacation rentals
  • Maryland Quiet Waters Park: 609 vacation rentals
  • U.S. Naval Academy: 584 vacation rentals
  • Captain Avery Museum: 603 vacation rentals

But there are many other points of interest around Chester listed on VRBO where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent houses in Chester?

Yes, of course. VRBO has 97 houses in Chester. Our other popular types of vacation rentals in Chester include:

  • Cottages: 24 rentals available
  • Estates: 7 rentals available
  • Townhomes: 6 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including apartments and more.

Can I rent golf rental rentals in Chester?

Absolutely, VRBO has 69 golf rental rentals in Chester. You have also many other possibilities in Chester area, including:

  • Beachfront rentals: 65 rentals
  • Beach view rentals: 17 rentals
  • Lake view rentals: 5 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with online bookable in Chester?

Yes, you can select your prefered vacation rental with online bookable among our 156 vacation rentals with online bookable available in Chester. Please use our search bar to access the selection of vacation rentals available.