Holiday rentals near Church Hill Theatre

We found 166 holiday rentals — enter your dates for availability

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August 2025

September 2025

If you'd like to stay close to Church Hill Theatre, take a look at private holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the amenities that you expect and more, which might include a hot tub and a washer and dryer. At the end of the day, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Church Hill Theatre

Showing deals for:14 Nov - 21 Nov

Exceptional

(22 reviews)

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Chestertown, MD

8% off

AU$1,906 per night

includes taxes & fees

Exceptional

(7 reviews)

Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Chestertown, MD

17% off

AU$636 per night

includes taxes & fees

Exceptional

(11 reviews)

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville, MD

17% off

AU$407 per night

includes taxes & fees

Exceptional

(115 reviews)

Peaceful getaway convenient to local amenities including beach, boating & food

Rock Hall, MD

8% off

AU$377 per night

includes taxes & fees

Exceptional

(48 reviews)

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

Rock Hall, MD

12% off

AU$391 per night

includes taxes & fees

Exceptional

(23 reviews)

Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler

Rock Hall, MD

8% off

AU$2,075 per night

includes taxes & fees

Exceptional

(11 reviews)

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Centreville, MD

8% off

AU$1,885 per night

includes taxes & fees

View from deck of brick patio, fire pit area, & pier w/ separate floating dock.

Exceptional

(99 reviews)

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

Chestertown, MD

8% off

AU$908 per night

includes taxes & fees

20982 Bayside Ave, across from town dock, close to harbor and restaurants

Exceptional

(61 reviews)

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Rock Hall, MD

8% off

AU$498 per night

includes taxes & fees

This photo is about 8 years old. The trees have grown up a little.

Exceptional

(20 reviews)

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Galena, MD

8% off

AU$994 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Church Hill Theatre

STONE RIVERSIDE COTTAGE is just a few steps from the SASSAFRAS RIVERS edge

Sleeps 4 · 1 bedroom · 1 bathroom

Store front - New Wine Bar - Coming June 2025

Grand home located right on Main St, walk to Chesapeake Bay & great restaurants

Sleeps 13 · 5 bedrooms · 4+ bathrooms

Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities

Sleeps 8 · 3 bedrooms · 3 bathrooms

Top rated rentals - Church Hill Theatre

House, pond, property. Private beach and Chesapeake Bay is behind far tree line.

Premier Host

Great place for a family reunion

Our family was gathered in the area for a wedding. Although we only had nine people sleeping here, we accommodated other relatives for meals and a crab feast. The house has several seating areas, including the beach area, where people could sit down and catch up. Had it been warmer weather, we would have also enjoyed the kayaks and paddle boards. Overall, it suited our needs perfectly.

Kathryn A.

Stayed Oct 2023

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value