Chesapeake Beach Holiday Homes
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Featured Holiday Homes in Chesapeake Beach

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

Rising Sun Bay View Cottage

Relax on Kent Island in 3 Bedroom Home w/Waterview

Spacious 4 Bedroom Home w/ Hot Tub

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

The Blue Crab Beach House - Free beach passes

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Beautiful Waterfront Retreat in Cambridge!
Holiday Accommodation Chesapeake Beach
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Chesapeake Beach are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Chesapeake Beach itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Chesapeake Beach holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Chesapeake Beach, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Chesapeake Beach with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Chesapeake Beach Holiday Homes essential information
Accommodation | 412 Holiday Homes |
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Lowest Price | NZ$180 |
Highest Price | NZ$1,207 |
Popular accommodation | The Cozy Crab- Your Charming Haven in Lovely North Beach!, The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill, Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown. , Rising Sun Bay View Cottage, Relax on Kent Island in 3 Bedroom Home w/Waterview, Spacious 4 Bedroom Home w/ Hot Tub, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, The Blue Crab Beach House - Free beach passes , Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Beautiful Waterfront Retreat in Cambridge! |
More accommodations in Chesapeake Beach
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Rod 'N' Reel Resort
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