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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 16 Apartments in Church Hill with updated reviews, rates, and availability.

Newly restored apartment in the heart of Chestertown
Fridge, microwave, oven, stovetop

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (21)
"We loved this apartment. The communication with the owner was very timely and clear!"
Newly restored apartment in the heart of Chestertown
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (27)
"Property is clean & comfortable. Great location for walking to downtown Chestertown shopping and restaurants."
Historic Downtown Garden Oasis with Private Patio
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (81)
"Clean, well appointed, plenty of space, all small amenities were thought of. We would definitely come back. Very responsive owner too!"
The price is AED 360
AED 579 total
includes taxes & fees
6 May - 7 May
First Floor Studio Apartment in Historic Chestertown
Carriage House Hideaway in Middle of Chestertown
Iron/ironing board, travel crib, free WiFi, bed sheets

Carriage House Hideaway in Middle of Chestertown

10.0 out of 10, Exceptional, (87)
"If I could give these hosts 10 stars, I would! They went above and beyond for me! Their kindness and helpfulness was way beyond what I would have expected from a host. The carriage house is adorable! It is comfy, clean and quiet. It is stocked with a coffee maker, a toaster, an air fryer, a microwave, etc. If you need it, it probably there!I just cannot say enough about these hosts and their adorable carriage house rental. "
Carriage House Hideaway in Middle of Chestertown
Relaxation Haven on the Shore near Choptank River
Fridge, microwave, oven, stovetop

Relaxation Haven on the Shore near Choptank River

10.0 out of 10, Exceptional, (4)
"We were attending a wedding in Easton, MD. This was the perfect place to use as a base while attending wedding and get togethers "
Relaxation Haven on the Shore near Choptank River
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (35)
"Clean and away from all the hustle and bustle, not to mention the views and lovely hosts! Don’t miss out on this if you want a relaxing trip, or if you do want to explore the area there’s plenty of great small towns in the area, also an easy drive to some of the most iconic cities along the Chesapeake Bay."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Waterfront Retreat with Private Dock and Beach
Miscellaneous

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (17)
"This property was exactly what we needed! The apartment was very clean and well maintained making it such a pleasant experience. Even though the property is shared with the owners, they weren’t constantly around or hovering over us allowing us to enjoy our time together. We loved having the dock and availability of the kayaks so we didn’t have to bring us along for the long trip there. We found some small shops and cute little towns along with a wonderful winery all within a short drive from...
The price is AED 643
AED 1,159 total
includes taxes & fees
27 Apr - 28 Apr
Waterfront Retreat with Private Dock and Beach
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

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

10.0 out of 10, Exceptional, (10)
"Fantastic accommodations! Many amenities! Friendly hostess! "
The price is AED 250
AED 459 total
includes taxes & fees
24 Apr - 25 Apr
Guest Suite for up to 2 in a Victorian on the Chester River
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Miscellaneous

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

10.0 out of 10, Exceptional, (4)
"A great place to chill out and enjoy what Rock Hall has to offer. It’s always great to come back to my childhood town. Rick is a great host and takes really good care of the property! We will be back."
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
1 bedroom, bed sheets

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.6 out of 10, Exceptional, (5)
"Thank you Lynn for having us. It was a short trip but worth it, especially being able to stay at the She Shed - clean, conveniently located, and quiet. We’ll definitely be back!"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

10.0 out of 10, Exceptional, (2)
"Just spent the weekend at Knot’s Landing and highly recommend it! The location is incredible with walk-ability to all of Main St and still close to the marina and the beach. The place was very clean and incredibly spacious. Check in and out was perfectly smooth and the host was responsive and helpful with the one question we had. 10/10 absolutely recommend!"
Knot's Landing, spacious Apt. downtown Rock Hall
Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm
Outdoor dining

Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm

9.8 out of 10, Exceptional, (50)
"This place is absolutely beautiful. So relaxing and management well let’s just say that they are the best people to be around. Looking forward to returning one day. Hated to leave"
Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm
Cute waterfront apartment -- 8 min from the beach!
Outdoor dining

Cute waterfront apartment -- 8 min from the beach!

10.0 out of 10, Exceptional, (6)
"We enjoyed our stay so much. It was so private and quiet. It was also nice to be able to bike ride where ever we needed to go. It was perfect!! We plan on going back soon!!"
Cute waterfront apartment -- 8 min from the beach!
Relax on the Eastern Shore of Kent Narrows in a King Bed
Smart TV, fireplace, DVD player, books

Relax on the Eastern Shore of Kent Narrows in a King Bed

10.0 out of 10, Exceptional, (12)
"This lovely apartment was spacious, clean and oh so comfy! Jackie is the perfect host and an amazing person! The special gifts that she left for us that made the stay even more special. The fresh eggs from her chickens were the best!! My only comment would be that the post on VRBO did not make it clear that this apartment was part of a larger home where the hosts live. Was a bit confusing to us upon arrival. Otherwise, would go back there in a heartbeat! Thanks, Jackie!"
Relax on the Eastern Shore of Kent Narrows in a King Bed
Belle Blu of Kent Narrows Grasonville, Maryland
3 bedrooms, desk, iron/ironing board, travel crib

Belle Blu of Kent Narrows Grasonville, Maryland

10.0 out of 10, Exceptional, (3)
"Well worth your efforts to stay with Jackie in Grasonville. It is an awesome spot with everything you need. Have never experienced a host so welcoming and the rental is brand new, clean, and spacious. Excellent option when wanting to stay close to Annapolis. Thank you Jackie!"
Belle Blu of Kent Narrows Grasonville, Maryland
Cozy Waterfront Apartment Chester, MD
Terrace/patio

Cozy Waterfront Apartment Chester, MD

The price is AED 496
AED 907 total
includes taxes & fees
21 May - 22 May
Cozy Waterfront Apartment Chester, MD
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Church Hill

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

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

10.0 out of 10, Exceptional, (183)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
Miscellaneous

Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD

10.0 out of 10, Exceptional, (3)
"This home was perfect for our 3 night stay. We came to spend time with our daughter who had moved to the area. The owners thought of everything and the little touches are what made this the perfect rental for our stay. Only downside was the weather did not allow us to enjoy the amazing views and cozy porches during our stay. Next time we visit with a group we will definitely stay here again!"
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
Stay in the landmark Lighthouse!
Beach

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (98)
"This is our second time staying at The Lighthouse and we had a wonderful time! It is perfect for three couples. The kitchen is large and fully equipped . The living room/dining room is spacious. The house was clean and ready for us. The property manager, Diane was responsive and very helpful. "
Stay in the landmark Lighthouse!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What's it like to stay at an apartment in Church Hill?
You might not have many choices within the heart of Church Hill, but Expedia can help you search for lodging accommodations within the larger area with similar amenities to an apartment. When you search on Expedia, you can use the filters to search for conveniences you might find in an apartment such as a kitchen. You can even filter by similar property types like vacation homes, condos, or cabins.
Are you thinking about an apartment for your stay?
An apartment is often more spacious than a traditional hotel room and comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home but also for couples who want to stay away from the tourist areas.
What's the top apartment for a stay in Church Hill?
Here are some of the top apartments in the area: First Floor Studio Apartment in Historic Chestertown: Located in Chestertown, 6 mi/9.7 km from the heart of Church Hill. Includes a private pool, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities are on site. WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: Located 20.7 mi/33.3 km away in Earleville. Free WiFi and Smart TVs are included. Historic Downtown Garden Oasis with Private Patio: It’s situated in Chestertown, 6.5 mi/10.5 km away. Includes free WiFi, outdoor space, and separate dining areas. Newly restored apartment in the heart of Chestertown: Located 6.3 mi/10.1 km away in Chestertown. Amenities include free WiFi. Access to onsite laundry facilities is available on site. Waterfront Retreat with Private Dock and Beach: It’s located in Worton, 14.3 mi/23.1 km from Church Hill. Includes free WiFi, sofa beds, and Smart TVs.
What will the weather be like during my trip to Church Hill?
Though weather is just one factor, it can really affect your travel plans, especially when you’re planning an extended stay in Church Hill. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Church Hill is 48 inches.
What should I see and do in Church Hill?
Explore the area and family-friendly sights such as Crumpton Auction, or get out into nature at a spot like Ferry Park. While here, Church Hill Theatre and Cassinelli Winery and Vineyards are other places worth a visit.
What's the best way to get to and around Church Hill?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Easton, MD (ESN-Easton - Newnam), which is located 23.2 mi (37.3 km) away from the heart of the city. Otherwise, look for flights into Baltimore, MD (MTN-Martin State), which is 26.7 mi (43 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.