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Vacation rentals in Chester

Vacation rentals in Chester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Waterfront Retreat
    Entire flat · 4 guests · 3 beds · 1 bathroom
    Waterfront Retreat

    Utilities included Apartment with Full kitchen, fully furnished, washer/dryer, two bedrooms, comfy couch, Wifi, Tivo, pet friendly, pool, pier with 220. Great water access to Eastern and Chesapeake Bay. Great restaurants. Access to exercise and pool room. 6 month minimum commitment. Oh best part you can pay monthly thru Airbnb and no one month Security Deposit!

    What guests are saying:

    “I’ll begin with the space itself; the pictures don’t even begin to do it justice! I obviously was impressed by the pictures and that’s why I originally looked into this location, but in person it’s even better! The space was perfect for 4 adults and a 4 month old baby; was only 10 minutes away from where we attended a wedding; nearby shopping for the items we invariably forgot, and was about an easy 30 minutes drive into the heart of Annapolis! But mostly, it was the quick and helpful responses from Rita each time I contacted her. We got to meet her, her husband, and their very friendly and welcoming dogs! Rita and Ed were most gracious hosts; I highly recommend their home if you ever need to stay in the area!”

  • Eastern Shore Charm on Winchester Creek
    SUPERHOSTEntire guest house · 2 guests · 1 bed · 1 bathroom
    Eastern Shore Charm on Winchester Creek

    My place is close to restaurants and dining and great views. You’ll love my place because of the comfy bed, the coziness, and the views. My place is good for couples, solo adventurers, and business travelers; sorry no kids. Need at least three days notice to book guest house, I like to be here when you arrive, thus schedule my social activities around bookings.

    What guests are saying:

    “A great spot to stay while visiting family for the holidays. Conveniently located right off the highway to make getting in and out easy. The guesthouse was clean and Judy provided some great snacks. Would definitely stay again!”

  • Halcyon house.  Lovely views on MD eastern shore.
    SUPERHOSTEntire flat · 3 guests · 1 bed · 1 bathroom
    Halcyon house. Lovely views on MD eastern shore.

    This charming apartment is located on the Chester River on Maryland's Eastern Shore and is conveniently located 20 minutes from Annapolis and 50 to Baltimore and Washington, D.C. Spectacular waterfront sunup and sunset views, a newly renovated apartment with all new appliances, and a well-stocked kitchen. There are many seafood restaurants and lots of outlet shopping and consignment/ antique shops nearby. The Cross Island trail for walking, biking etc starts at the local park and ends at bay

    What guests are saying:

    “Really enjoyed my stay and was a perfect place to escape the city for a few days. Weather wasn’t great during my stay but I look forward to going back and using the kayaks. Margaret was very helpful and with no booking the day after I was able to do a late checkout.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chester holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chester

Boutique by the Bay
SUPERHOSTEntire flat
Boutique by the Bay
Price:€156 / night
Kent Island Beautiful 4 BR home, central location!
SUPERHOSTEntire house
Kent Island Beautiful 4 BR home, central location!
Price:€320 / night
Wye River Cottage and Horse Barn
SUPERHOSTEntire cottage
Wye River Cottage and Horse Barn
Price:€120 / night
Kent Island Haven - A Waterfront Getaway
SUPERHOSTEntire guest suite
Kent Island Haven - A Waterfront Getaway
Price:€133 / night
Cottage on the Bay - Kent Island
Entire cottage
Cottage on the Bay - Kent Island
Price:€333 / night
Chester Riverfront At Kent Narrows
SUPERHOSTEntire flat
Chester Riverfront At Kent Narrows
Price:€120 / night
Holiday on the Bay, Kent Island Beach House
SUPERHOSTEntire house
Holiday on the Bay, Kent Island Beach House
Price:€445 / night
Cape Cod Bed and Bath
Private room
Cape Cod Bed and Bath
Price:€76 / night
3BR/2BT/4PK Entire House By Chesapeake Beach Club
SUPERHOSTEntire house
3BR/2BT/4PK Entire House By Chesapeake Beach Club
Price:€204 / night
The Kent Island House
SUPERHOSTEntire house
The Kent Island House
Price:€182 / night
Abay Palace of Kent Narrows in a King  Bed!
SUPERHOSTEntire flat
Abay Palace of Kent Narrows in a King Bed!
Price:€129 / night
Kent Island Beach House II by the Kentmorr Marina
SUPERHOSTEntire house
Kent Island Beach House II by the Kentmorr Marina
Price:€444 / night
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