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Top Holiday Rentals in Church Hill

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (50)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (35)
"Was a great vacation hope to come back next year!"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

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

9.8 out of 10, Exceptional, (40)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (30)
"We really enjoyed our stay. Looking forward to staying again!"
The price is £229
includes taxes & fees
8 Jul - 9 Jul
Cass-N-Reel Luxury Houseboat

Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.

10.0 out of 10, Exceptional, (7)
"Property was extremely well kempt. It was beautiful. We enjoyed ourselves there and would recommend it to others."
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.

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

10.0 out of 10, Exceptional, (45)
"Cool house within walking distance to beach, restaurant and marinas"
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

9.8 out of 10, Exceptional, (88)
"In the area for a wedding. This was a great place for the family to gather in between events. Communication with the owners is top notch. We highly recommend it. "
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (20)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
The price is £280
includes taxes & fees
1 Jul - 2 Jul
Waterfront Retreat with Private Dock and Beach

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (96)
"This is a great getaway place!! Very nice on the water. Lots to do in the area! Tiki Bars restaurants must stop while traveling or vacationing!"
Cass-Away Luxury Houseboat

Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

9.8 out of 10, Exceptional, (11)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!

10.0 out of 10, Exceptional, (23)
"Good location."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (2)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (99)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown

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

9.8 out of 10, Exceptional, (7)
"Located in a quite area and the host were incredible"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

10.0 out of 10, Exceptional, (122)
"Nice big home with lots of room to be together"
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (5)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is £326
includes taxes & fees
30 Jun - 1 Jul
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (15)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

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

9.8 out of 10, Exceptional, (113)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food

Sprawling Waterfront Home with views, Dock and In-Home Theatre

Sprawling Waterfront Home with views, Dock and In-Home Theatre

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (34)
"We love this place and would stay here again in a heartbeat. Beautifully decorated with so many details and touches that make it extra special. Such a well done lovely property!!!"
Historic Downtown Garden Oasis with Private Patio
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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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 air conditioning 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 Rolphs Wharf Marina 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.