Chestertown Holiday Homes
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Featured Holiday Homes in Chestertown
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
River Front, Private Single Family Home
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
BAYSIDE BUNGALOW
Charming Historic Townhouse Steps From USNA
Serene waterfront home with kayaks, paddle board, grill, firepit, W/D, and AC
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home
Waterfront Cottage on the Eastern Shore
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Holiday Accommodation Chestertown
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 Chestertown 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 Chestertown itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Chestertown 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 Chestertown, 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 Chestertown 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.
Chestertown Holiday Homes essential information
Accommodation | 393 Holiday Homes |
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Lowest Price | NZ$90 |
Highest Price | NZ$1,291 |
Popular accommodation | ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Spacious 2 bedroom duplex located conveniently near Route 50 East and West. , River Front, Private Single Family Home, Waterfront w/private pier, pool, Hot Tub, kayaks and in town., BAYSIDE BUNGALOW, Charming Historic Townhouse Steps From USNA, Serene waterfront home with kayaks, paddle board, grill, firepit, W/D, and AC, Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home, Waterfront Cottage on the Eastern Shore, Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!, Charming brick home with patio, WiFi, AC, & W/D - walk to everything, Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view! |
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Quality Inn & Suites Bel Air I-95 Exit 77A
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