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Vacation rentals in Chesapeake Beach

Vacation rentals in Chesapeake Beach

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chesapeake Beach

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

  • Artists amazing sunrise water retreat!
    SUPERHOSTEntire house · 2 guests · 1 bed · 2 bathrooms
    Artists amazing sunrise water retreat!

    Wake up to AMAZING sunrises over the water. Visit our beautiful little beach community where everyone says hello as you walk one of our several board walks on the bay or a back creek. This a place of serenity where you can come relax and get away from it all. 25 minutes from Annapolis and 45 minutes to the monuments in DC. Best for a couple retreat or single person who want to get away from it all. We accommodate couples and singles. Welcome.

    What guests are saying:

    “When creating this review, Airbnb asked what I liked most about my stay and it was truly difficult in narrowing it down to one option as there were so many things I enjoyed about my stay. But Jacqueline’s hospitality had to take the prize as she immediately made me feel at home. I enjoyed our conversations and the “surprises” that would periodically appear on the front porch. This is an amazing place to stay with the most relaxing views. Even with all the anxiety surrounding COVID-19 and social distancing, the people in the town were friendly and welcoming. I felt like a welcome guest rather than an intrusive outsider. Other reviews mentioned the sunrise and I can’t emphasize enough what a wonderful sight that sunrise is to behold. You look out of your bed and there it is! I’m not one to ramble on in a review so I’ll bring it to a close. I very much recommend this rental. I’ve been looking for a new go-to vacation spot and I think I may have found just that. I’ll be back.”

  • Nice Guest Suite at Chesapeake Bay
    Entire guest suite · 2 guests · 2 beds · 1 bathroom
    Nice Guest Suite at Chesapeake Bay

    Come and relax in our modern & comfortable guest suite and enjoy a small-town setting with amazing Chesapeake Bay views. Unbelievable sunrises and sunsets. A short drive from Washington DC (45 min), Annapolis (30 Min), or Baltimore (1 hr). Groceries, boardwalks, restaurants are all within walking distances. Bring your fishing poles as you can have great fishing from the bayside of our house. Enjoy hi-speed Internet as well as strong wifi through Xfinity cable service.

    What guests are saying:

    “Farhad and Rhonda are wonderful people ! They were always very quick to respond if we had any questions, and they had lots of great recommendations of things to do in the area. Their guest suite was spotless, coffee in the morning was a great perk, and the view from their property was incredible ! We loved having morning coffee and meals at the table that overlooked the water. If you’re looking for calming ocean sounds, this will probably be the perfect place to stay!”

  • Bayside Cottage
    SUPERHOSTEntire house · 6 guests · 3 beds · 1 bathroom
    Bayside Cottage

    ***Due to Covid19 the beaches in North Beach and Chesapeake Beach are closed until further notice*** Newly renovated! Enjoy the entire home. Close to everything! Only 2.5 miles from Herrington on the Bay; Close to Beach, boardwalk, Water park, restaurants, bars, local shops, antiques! . Off street/ample parking, fenced back yard, screened front porch with rocking chairs. Explore the quaint town of North Beach, charter a fishing boat, go antiquing, or just sit back and relax.

    What guests are saying:

    “The Chesapeake Beach House is centrally located between Chesapeake and North Beach-- both are walking/biking distance. It is worth noting that the house is right on the main road. There's a great screened in porch with rocking chairs. The kitchen is bright and welcoming. If you have several people staying, you might want to bring an extra mirror for getting ready as the little bedroom doesn't have one. The house was perfect for vacation and I would highly recommend it to others.”

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Popular amenities for Chesapeake Beach holiday rentals

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

Other great holiday rentals in Chesapeake Beach

Chesapeake Bay Beachfront Cottage, A Hidden Secret
SUPERHOSTEntire cottage
Chesapeake Bay Beachfront Cottage, A Hidden Secret
Price:€267 / night
CUTE CHESAPEAKE BEACH COTTAGE  CLOSE TO THE BAY
SUPERHOSTEntire guest house
CUTE CHESAPEAKE BEACH COTTAGE CLOSE TO THE BAY
Price:€79 / night
Bayview at Hilltop
SUPERHOSTPrivate room
Bayview at Hilltop
Price:€58 / night
Brand new apartment
SUPERHOSTEntire guest suite
Brand new apartment
Price:€53 / night
Spacious apartment, private entrance - water views
SUPERHOSTEntire house
Spacious apartment, private entrance - water views
Price:€85 / night
Last Stop Cozy Cottage near North Beach, MD
Entire cottage
Last Stop Cozy Cottage near North Beach, MD
Price:€156 / night
Boutique by the Bay
SUPERHOSTEntire flat
Boutique by the Bay
Price:€156 / night
Chesapeake Bay Cottage
Entire cottage
Chesapeake Bay Cottage
Price:€218 / night
The Little Gypsy BoHome on the Bay!
SUPERHOSTEntire house
The Little Gypsy BoHome on the Bay!
Price:€534 / night
Burkingham
SUPERHOSTPrivate room
Burkingham
Price:€28 / night
Crystal Cove Retreat | A Place of Zen
SUPERHOSTEntire house
Crystal Cove Retreat | A Place of Zen
Price:€107 / night
Full house rental in Twin Beach. 1 bk from the Bay
SUPERHOSTEntire cottage
Full house rental in Twin Beach. 1 bk from the Bay
Price:€124 / night
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