Church Hill Vacation Rentals

Vacation Rentals in Church Hill

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (18)
"This is a excellent cottage for a short getaway. As the listing states, the cottage is small so only big enough for 1-2 people. There is a nice refrigerator and microwave to heat things up but no facilities for cooking. Paul and Chris are very friendly and helpful. Their dog Vinny is also friendly. We came for a triathlon and the porch was a covered so we could keep our bikes there. The sauna was also great to use after our triathlon."
The price is $175
$267 total
includes taxes & fees
Jun 11 - Jun 12
BAYSIDE BUNGALOW
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (15)
"My friends, our wives, and kids loved our stay. Everything exceeded expectations. We especially enjoyed the backyard where we played yard games, grilled, and enjoyed the river."
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
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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, (19)
"Cozy & elegant ☀️ a clean bright space."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
200 steps to the beach!
Interior
200 steps to the beach!
10.0 out of 10, Exceptional, (76)
"House was beautifully decorated, updated, clean, and as advertised, steps from the beach!!! We had everything we needed for meal prep, including a charcoal grill. Enjoyed grilling fresh fish for dinner one night!"
200 steps to the beach!
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Balcony
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun loungers, beach towels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (90)
"We enjoyed meeting the hosts and their llamas and emus. The home had everything we needed for our stay, and the view of the water from the house could not be better. We watch the sunsets wherever we go, and the colors were spectacular. There were plenty of things to do, and the restaurants were a short drive away. Thank you for sharing this property with others."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Waterfront Sunset Bayview: sleeps 6
Beach
Waterfront Sunset Bayview: sleeps 6
10.0 out of 10, Exceptional, (1)
"Beautiful home on the water. Everything we needed for a lovely stay on the island."
Waterfront Sunset Bayview: sleeps 6
Cass-Away Luxury Houseboat
Smart TV
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, (81)
"We had a bit of trouble figuring out the TV, and Kirby was most helpful and responsive, even at 8:30pm! The proximity of several walkable seafood restaurants was handy, and tasteful. The traffic on both road and water was actually entertaining, to the point of getting unduly mesmerized by the drawbridge routine. For a nice touch, a great blue heron flew right under our kitchen window."
The price is $150
$363 total
includes taxes & fees
Jun 16 - Jun 17
Cass-Away Luxury Houseboat
Rambling Victorian Beach House on Maryland's Eastern Shore
Beach nearby, sun loungers, beach towels
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, (13)
"Our group of couples + kids enjoyed our getaway to the Eastern Shore. Betterton was a great home base to visit our alma mater, Washington College, in Chestertown. There, we visited the farmers market and waterfront park & playground with the kids. Back in Betterton, the house fit our group well. Plenty of bedrooms, bathrooms and space for each family. The kids & adults enjoyed spending time lounging in the third floor living room. We were pleased that the house had plenty of games, kids toys,...
Rambling Victorian Beach House on Maryland's Eastern Shore
Family-Friendly Cottage, Walk to the Beach!
Property grounds
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, (14)
"Great location "
Family-Friendly Cottage, Walk to the Beach!
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (60)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is $110
$164 total
includes taxes & fees
Jun 11 - Jun 12
First Floor Studio Apartment in Historic Chestertown
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Property grounds
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
10.0 out of 10, Exceptional, (3)
"Wonderful rental home for our family with great pool and river view. Swimming every day in the pool was so much fun for everyone, kayaks, and paddle boards were great since we did not have to bring anything. Children fished every night on the dock. We played lots of games inside and out everyday and enjoyed the Nature all around to see, birds, deer, fish, frogs and small animals. Our family felt like they had their own getaway for a wonderful vacation. Thank you for everything."
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Eastern Shore beach cottage get-away
Sun loungers
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (122)
"The cozy cottage is perfectly maintained and well equipped. The bay view is as advertised and lovely. The location in Rock Hall is ideal, quiet and convenient to everything. The property manager is responsive and informative. We had a great, relaxing getaway weekend and look forward to returning."
Eastern Shore beach cottage get-away
Coastal Kent Narrows Home on Bay
Fridge, microwave, oven, stovetop
Coastal Kent Narrows Home on Bay
9.2 out of 10, Wonderful, (5)
"Very nice place to stay, right on the bay"
The price is $185
$399 total
includes taxes & fees
Jun 11 - Jun 12
Coastal Kent Narrows Home on Bay
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Fridge, microwave, oven, stovetop
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
10.0 out of 10, Exceptional, (2)
"Couldn’t have asked for a better place for us. Lots of room and quiet neighborhood."
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Balcony
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
10.0 out of 10, Exceptional, (40)
"Beautiful property. Needs better towels and linens. Kitchen is well equipped. Living areas are spacious and comfortable"
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, (104)
"We were there for the local triathlon weekend. This property was centrally located within easy walking distance to the water, race site, and restaurants. We didn't get much of a chance to explore downtown but still had a great time relaxing and talking to the locals!"
Peaceful getaway convenient to local amenities including beach, boating & food
Cass-N-Reel Luxury Houseboat
View from property
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (11)
"We enjoyed the property and the proximity to bars/restaurants. We enjoyed the view from the back porch and it is a nice place to relax. We would definitely recommend staying and look forward to booking another stay in the future."
The price is $150
$334 total
includes taxes & fees
Jun 21 - Jun 22
Cass-N-Reel Luxury Houseboat
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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.

Other types of properties in Church Hill you may be interested in

Hyatt Place Kent Narrows & Marina
Terrace/patio
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (319)
"Very impressed by breakfast service, availability of bar on site and waterfront seating. "
The price is $177
$196 total
includes taxes & fees
Jun 19 - Jun 20
Hyatt Place Kent Narrows & Marina
Best Western Kent Narrows Inn
Exterior
Best Western Kent Narrows Inn
2.5 star property
8.0 out of 10, Very Good, (1004)
"Great price for the area, good location, clean, friendly service staff, allows pets."
The price is $128
$142 total
includes taxes & fees
Jun 17 - Jun 18
Best Western Kent Narrows Inn
Hilton Garden Inn Kent Island
Terrace/patio
Hilton Garden Inn Kent Island
3.0 star property
9.0 out of 10, Wonderful, (776)
"Great hotel to stay at. Lots of options for eating dinner there are two places within walking distance "
The price is $178
$197 total
includes taxes & fees
Jun 19 - Jun 20
Hilton Garden Inn Kent Island
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.

Everything you need to know about Church Hill vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Church Hill vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Church Hill vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Church Hill vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Church Hill. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Church Hill in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $110 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Church Hill rentals

At Expedia, we put the best Church Hill vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Church Hill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Church Hill vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Church Hill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Church Hill?

Yes, we give you a choice of vacation rentals near the most popular sights in Church Hill, or you can choose a more remote option if you want a relaxing place to stay. Church Hill is known for its wineries.

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

Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.: Located near Church Hill, this vacation home rental is located on the waterfront and has a private balcony, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Church Hill?

Explore the area and cultural attractions such as Church Hill Theatre, or visit a family-friendly sight such as Crumpton Auction. Cassinelli Winery and Vineyards and Rolphs Wharf Marina are a couple of places you'll find in the larger area.

What are vacation rentals like in Church Hill?

Vacation rentals are private accommodations you can book for a couple days or more in Church Hill. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for small groups.

Recent reviews of Church Hill properties
Expedia verified reviews

Quality Inn

Quality Inn

5/5 Excellent
"The room was just right for the three of us."
A verified traveler from Wynnewood stayed at Quality Inn
Posted 3 hours ago
Quality Inn