Church Hill Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Church Hill holiday rentals

1. First Floor Studio Apartment in Historic Chestertown

Chestertown

S G.

HK$1,245 total

includes taxes & fees

2 Sept - 3 Sept

2. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveller

HK$2,761 total

includes taxes & fees

31 Aug - 1 Sept

3. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

HK$2,269 total

includes taxes & fees

8 Sept - 9 Sept

4. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

HK$3,923 total

includes taxes & fees

9 Sept - 10 Sept

5. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

HK$2,215 total

includes taxes & fees

1 Sept - 2 Sept

6. Family Retreat at Lansdowne Manor

Centreville

HK$2,951 total

includes taxes & fees

2 Sept - 3 Sept

7. Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Riley B.

HK$981 total

includes taxes & fees

10 Sept - 11 Sept

8. BAYSIDE BUNGALOW

Rock Hall

Diane V.

HK$2,475 total

includes taxes & fees

31 Aug - 1 Sept

9. Beachcomber Suite

Kent County

"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...

Lisa E.

HK$1,554 total

includes taxes & fees

31 Aug - 1 Sept

10. Waterfront Retreat with Private Dock and Beach

Worton

Max G.

HK$2,952 total

includes taxes & fees

31 Aug - 1 Sept

11. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

Hartly

HK$1,197 total

includes taxes & fees

31 Aug - 1 Sept

12. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

lisa p.

HK$2,257 total

includes taxes & fees

31 Aug - 1 Sept

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

Grasonville

Robin

HK$3,324 total

includes taxes & fees

1 Sept - 2 Sept

14. Cass-Away Luxury Houseboat

Grasonville

Jamie L.

HK$2,467 total

includes taxes & fees

25 Sept - 26 Sept

15. Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

HK$2,851 total

includes taxes & fees

29 Sept - 30 Sept

16. Turtle Cove Room

Kent County

HK$1,366 total

includes taxes & fees

31 Aug - 1 Sept

17. Turnbridge Manor

Denton

Glenn S.

HK$4,837 total

includes taxes & fees

1 Sept - 2 Sept

18. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Dover

Richard B.

HK$1,387 total

includes taxes & fees

6 Sept - 7 Sept

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Top Church Hill Hotel Reviews

Best Western Kent Narrows Inn

8/10 Good

"Location was great, beds were comfortable and the room was clean."

240' Private Beachfront @Kent Island Love Point - Great for Families

10/10 Excellent

"The property was beautiful!! The beach area was so peaceful and already had Adirondack chairs and a table ready for us. It was an area just for the group that didn’t have to be shared with any one. Plus kayaks and life vest! The rooms were nicely made up and plenty of bed for the whole group.We enjoyed our meals together inside and out on the screeded porches which was so enjoyable. The fire pit was nicely made to sit around at night, also chairs were already provided. The kitchen was stocked with everything we needed for meal time including extra paper towels, tissues, napkins, and kitchen pots, pans, spices and even small things we needed like pens, a lighter, detergent, towels (for inside and out) and extra dog bowl! Being dog friendly was a huge huge huge plus the actual reason why we picked this listing over others! Every one was welcomed.The host answered every question I had quickly! The entries group, kids, adults and dogs all really enjoyed the home and the property!"

Inn at Huntingfield Creek

10/10 Excellent

"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10/10 Excellent

"The stay was very enjoyable. The hosts were friendly and thoughtful. Sunsets were great too. The members of the community we met were very friendly. The Grille up the street has excellent food. We did hike the 6.5 miles of trails at Bohemia River State Park."

Island Life! Kent Island Waterfront with Pool-Bring your boat!

10/10 Excellent

"We really enjoyed our stay at this spot while visiting our son for Plebe Parents Weekend at USNA. Had plenty of space to relax and unwind and communication was great throughout. One thing that wasn't as clear until arrival was that this is a guest house above garage next to main house where owner resides - therefore the pool/hot tub/outdoor space isn't private but shared. Wasn't a big deal to us but could to know beforehand. Really enjoyed the peaceful setting and was great to have the pool to cool off in with hot August humidity."

Find out more about Church Hill

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Frequently asked questions

Can I find holiday rentals in Church Hill?

Yes, there are holiday rentals close to the most popular sights in Church Hill, or you can select a more secluded option if you're looking for a relaxing stay. Church Hill is known for its wineries.

What are some of the best holiday rentals that Church Hill has to offer?

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining: This holiday home rental outside of Church Hill is located near the beach, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Church Hill?

Explore the area and cultural attractions such as Church Hill Theatre, or visit one of the family-friendly sights such as Crumpton Auction. Cassinelli Winery and Vineyards and Chestertown Historic District are a couple of places you'll find in the wider area.

What are holiday rentals like in Church Hill?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Church Hill. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips.

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Check prices for these dates

Our top choices for Church Hill holiday rentals

1. First Floor Studio Apartment in Historic Chestertown

2. Newly restored apartment in the heart of Chestertown

3. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

4. Wren Retweet- Country Estate in Center of C’Town

5. Secluded Cottage in Middle of Chestertown

6. Family Retreat at Lansdowne Manor

7. Guest Suite for up to 2 in a Victorian on the Chester River

8. BAYSIDE BUNGALOW

9. Beachcomber Suite

10. Waterfront Retreat with Private Dock and Beach

11. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

12. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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

14. Cass-Away Luxury Houseboat

15. Bayside Cottage steps from Rock Hall Harbor

16. Turtle Cove Room

17. Turnbridge Manor

18. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Find holiday rentals that suit your style

Top Church Hill Hotel Reviews

Best Western Kent Narrows Inn

The Inn at Chesapeake Bay Beach Club

Kent Island Resort

Best Western Denton Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

240' Private Beachfront @Kent Island Love Point - Great for Families

Inn at Huntingfield Creek

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Find out more about Church Hill

Frequently asked questions

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