Still Pond Holiday Rentals

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Holiday Rentals in Still Pond

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (75)
"EasyvPeasy place."
The price is AU$246
includes taxes & fees
27 Nov - 28 Nov
First Floor Studio Apartment in Historic Chestertown

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.8 out of 10, Exceptional, (26)
"The house is spacious (more than the photos may lead you to believe), with numerous gathering centers inside and out. My guests enjoyed the dock at sunset and the fire pit by the water. The patio under the house had a charcoal grill and ample space for tables and chairs. Though our weekend had perfect weather, the covered patio made the place "weatherproof" had it rained. There is tons of parking, and a beautiful view over the water. The Host was readily available via VRBO messaging, Usually...
Waterfront Oasis w/ Private Dock, 3BR/2BA

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (22)
"The pictures dont do this rental house justice. It was very clean and wonderfully decorated. The seperate unit was ideal for my daughter and her family. The "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

10.0 out of 10, Exceptional, (48)
"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.8 out of 10, Exceptional, (40)
"Very quaint and cute cottage really enjoyed sleeping on the porch , The sound of the waves because it was windy was so soothing. I felt We were on a sailboat."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (61)
"What an amazing place... the sunsets, the house, the pool, the amenities... absolutely everything was perfect! The owner was super helpful! "
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (23)
"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."
Waterfront family resort Lodge with private pier, game room and bar

Historic home in the heart of Main Street- walkable to shops and restaurants

10.0 out of 10, Exceptional, (9)
"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."
The price is AU$711
includes taxes & fees
25 Nov - 26 Nov
Historic home in the heart of Main Street- walkable to shops and restaurants

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (10)
"Couple little things were annoying. Overall a place/property we love. This was our third visit and plan for another."
Stunning waterfront villa with indoor pool and kids swing set and play area.

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (18)
"Wonderful place to stay!"
Amazing Waterfront Home on the Bush River

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is AU$418
includes taxes & fees
24 Nov - 25 Nov
BAYSIDE BUNGALOW

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is AU$795
includes taxes & fees
25 Nov - 26 Nov
Historic Chesapeake City Stay

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook

BEACH WITHOUT THE BUSTLE

10.0 out of 10, Exceptional, (26)
"We enjoyed our stay. Condo was comfortable and very clean. It provided convenient access for our weekend plans in Kennedyville and Chestertown."
BEACH WITHOUT THE BUSTLE

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

10.0 out of 10, Exceptional, (31)
"We had my daughter's wedding at this beautiful villa. The views were absolutely amazing! The house is very spacious and accommodated our family. The sunsets were spectacular. Everyone enjoyed the pool, hot tub, and all the other activities this house had to offer"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, 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 types of properties in Still Pond you may be interested in

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 star property
7.2 out of 10, Good, (1004)
"The breakfast was very basic, no meat, eggs juice or danish etc."
The price is AU$87
includes taxes & fees
1 Dec - 2 Dec
Quality Inn & Suites Bel Air I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

2.5 star property
8.2 out of 10, Very good, (1003)
"Clean , warm and inviting. Quiet ambiance and the Staff was excellent. Thank you "
The price is AU$98
includes taxes & fees
1 Dec - 2 Dec
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Aberdeen-APG

2.5 star property
8.8 out of 10, Excellent, (1034)
"Wonderful hotel "
The price is AU$144
includes taxes & fees
22 Dec - 23 Dec
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Still Pond?

Yes, there are holiday rentals close to the most popular sights in Still Pond, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Still Pond has to offer?

Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16: This holiday home rental outside of Still Pond is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of an arcade/games room in this rental home to help you unwind.

What can I see and do in Still Pond?

While exploring the area, visit family-friendly sights like Havre de Grace Maritime Museum, or get outside and enjoy nature at Betterton Beach. Washington College and Elk Neck State Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Still Pond?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Still Pond. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.