House in Maryland
10 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental
Welcome To Paradise!
Experience Waterfront luxury at this renovated retreat in a very quiet Chestertown neighborhood. The home features an open layout, spacious living room with sweeping bay views. Enjoy the private guest house, heated pool, private beach and spacious deck for some of the most beautiful sunsets you`ve ever seen. Just minutes from historic downtown, experience comfort with coastal charm—perfect for relaxing, entertaining, or exploring the Eastern Shore.
Some days you simply won`t want to leave the house! Enjoy the sparkling pool with lounge chairs. The expansive waterfront porch is the perfect spot for a morning coffee or enjoying the best sunset views on the East Coast. The back patio also includes an outdoor dining area, hot tub, sauna, and the spacious guest house deck. Fire up the grill or black stone for a crab feast, or simply relax as sailboats drift by.
With a quiet neighborhood and some of the most incredible views, this is an ideal spot for a couples’ retreat, family vacation, or friends’ getaway.
BRING YOUR BOAT! We are right up the road from Tolchester Marina. They rent slips for an average of $100 per night.
The Property Layout Consists Of The Main Home and a Guest House Next To The Pool
THE INTERIOR SPACE:
Lightning-fast Wi-Fi
Laundry area with washer + dryer (detergent provided)
Multiple sitting areas with plush furniture
Single-level main home plus separate guest house
KITCHEN + DINING AREA (Main Home):
- Fully-equipped kitchen with cooking + baking essentials (no food)
- Large dining table for 6
- Kitchen island with seating
- Stove + oven
- Refrigerator + freezer
- Microwave
- Dishwasher (detergent provided)
- Coffee maker + mugs
- Kitchen knife block set
- Dishes, silverware, glasses
LIVING ROOM:
- Smart TV
- Comfortable sofa and armchairs
- Throw pillows + blankets
THE SLEEPING ARRANGEMENTS – Main Home + Guest House:
- Bedroom 1 (Master): King bed with an expansive Bathroom
- Bedroom 2: King Bed + Smart TV
- Bedroom 3: King Bed
- Guest House (Bedroom 4) Sleeps 4: Open living/sleeping area with pull down Queen bed and pull out sofa, kitchen, full bath, and balcony with water views
BATHROOMS – 3.5:
- Bathroom 1: Full bath with walk-in shower, double vanity (In the Master)
- Bathroom 2: Full bath with tub/shower combo (In Between Bedrooms Two and Three)
- Bathroom 3: Full bath with shower (GUEST HOUSE)
- Half bath: Powder room off main living area
THE OUTDOOR SPACE:
- Private pool with lounge chairs
- Spacious deck with dining table
- Gas grill
- Blackstone griddle
- Expansive lawn with water frontage
- Parking for multiple vehicles in the driveway
- Garage / Arcade Room
- Changing room for pool use
- Storage for water toys
- Outdoor chairs
LOCAL FAVORITES:
- Historic Downtown Chestertown – 10 minutes
- Washington College – 10 minutes
- Eastern Neck National Wildlife Refuge – 20 minutes
- Rock Hall (waterfront dining & marinas) – 25 minutes
- Baltimore – ~1.5 hours
- Washington, DC – ~1.5 hours
The house, pool, are exclusively yours, without interruption during your stay, so relax, unwind, and make yourself at home.
A Few Additional Notes:
1. Please respect the neighborhood quiet hours from 10PM - 8AM
2. Pool Heat: This property is equipped with pool heat. Heat is turned on from May 1st - May 30th, and again September 1st - 15th and is included with your stay at no extra costs. The temp is set to 80 degrees (or around there). Pool heat does not mean the pool water will be hot it just makes it a comfortable temp to swim in.
3. The pool is closed for the Winter between September 15th - May 1st so please be sure to plan your vacation accordingly
4. Upon booking, each guest will receive a guest rental agreement. This must be signed before the House Manual (which includes access instructions for the property) is sent.
5. Pet Policy: This property is NOT pet friendly. Please note, if we find evidence of an unauthorized pet in the home, we will ask for it to be removed immediately and guests will be charged a $400 non-refundable fine. This is also grounds for immediate removal of the guests from the home.
Experience Waterfront luxury at this renovated retreat in a very quiet Chestertown neighborhood. The home features an open layout, spacious living room with sweeping bay views. Enjoy the private guest house, heated pool, private beach and spacious deck for some of the most beautiful sunsets you`ve ever seen. Just minutes from historic downtown, experience comfort with coastal charm—perfect for relaxing, entertaining, or exploring the Eastern Shore.
Some days you simply won`t want to leave the house! Enjoy the sparkling pool with lounge chairs. The expansive waterfront porch is the perfect spot for a morning coffee or enjoying the best sunset views on the East Coast. The back patio also includes an outdoor dining area, hot tub, sauna, and the spacious guest house deck. Fire up the grill or black stone for a crab feast, or simply relax as sailboats drift by.
With a quiet neighborhood and some of the most incredible views, this is an ideal spot for a couples’ retreat, family vacation, or friends’ getaway.
BRING YOUR BOAT! We are right up the road from Tolchester Marina. They rent slips for an average of $100 per night.
The Property Layout Consists Of The Main Home and a Guest House Next To The Pool
THE INTERIOR SPACE:
Lightning-fast Wi-Fi
Laundry area with washer + dryer (detergent provided)
Multiple sitting areas with plush furniture
Single-level main home plus separate guest house
KITCHEN + DINING AREA (Main Home):
- Fully-equipped kitchen with cooking + baking essentials (no food)
- Large dining table for 6
- Kitchen island with seating
- Stove + oven
- Refrigerator + freezer
- Microwave
- Dishwasher (detergent provided)
- Coffee maker + mugs
- Kitchen knife block set
- Dishes, silverware, glasses
LIVING ROOM:
- Smart TV
- Comfortable sofa and armchairs
- Throw pillows + blankets
THE SLEEPING ARRANGEMENTS – Main Home + Guest House:
- Bedroom 1 (Master): King bed with an expansive Bathroom
- Bedroom 2: King Bed + Smart TV
- Bedroom 3: King Bed
- Guest House (Bedroom 4) Sleeps 4: Open living/sleeping area with pull down Queen bed and pull out sofa, kitchen, full bath, and balcony with water views
BATHROOMS – 3.5:
- Bathroom 1: Full bath with walk-in shower, double vanity (In the Master)
- Bathroom 2: Full bath with tub/shower combo (In Between Bedrooms Two and Three)
- Bathroom 3: Full bath with shower (GUEST HOUSE)
- Half bath: Powder room off main living area
THE OUTDOOR SPACE:
- Private pool with lounge chairs
- Spacious deck with dining table
- Gas grill
- Blackstone griddle
- Expansive lawn with water frontage
- Parking for multiple vehicles in the driveway
- Garage / Arcade Room
- Changing room for pool use
- Storage for water toys
- Outdoor chairs
LOCAL FAVORITES:
- Historic Downtown Chestertown – 10 minutes
- Washington College – 10 minutes
- Eastern Neck National Wildlife Refuge – 20 minutes
- Rock Hall (waterfront dining & marinas) – 25 minutes
- Baltimore – ~1.5 hours
- Washington, DC – ~1.5 hours
The house, pool, are exclusively yours, without interruption during your stay, so relax, unwind, and make yourself at home.
A Few Additional Notes:
1. Please respect the neighborhood quiet hours from 10PM - 8AM
2. Pool Heat: This property is equipped with pool heat. Heat is turned on from May 1st - May 30th, and again September 1st - 15th and is included with your stay at no extra costs. The temp is set to 80 degrees (or around there). Pool heat does not mean the pool water will be hot it just makes it a comfortable temp to swim in.
3. The pool is closed for the Winter between September 15th - May 1st so please be sure to plan your vacation accordingly
4. Upon booking, each guest will receive a guest rental agreement. This must be signed before the House Manual (which includes access instructions for the property) is sent.
5. Pet Policy: This property is NOT pet friendly. Please note, if we find evidence of an unauthorized pet in the home, we will ask for it to be removed immediately and guests will be charged a $400 non-refundable fine. This is also grounds for immediate removal of the guests from the home.
Amenities at The Waterfront Retreat- With Sauna and Hot Tub!
Non-smoking
No pets allowed
Family friendly
Map of Maryland
Ratings and reviews
10 / 10Outstanding·Jan 2026
My family spent Christmas at the Waterfront Retreat and will always remember the week! There was plenty of room as well as entertainment options. The kitchen is very easy to cook in with a very large island to work, visit and/or eat on. The surrounding windows gave views to the bay to see sunsets, waterfowl and ships as they passed by. The game room was a big hit with the children and the hot tub and sauna saw lots of use. We enjoyed our stay!
$$$$
Top rated by guests
10Outstanding
(2 Ratings)
"My family spent Christmas at the Waterfront Retreat and will always remember the week! There was plenty of room as well as entertainment options. The kitchen is very easy to cook in with a very larg..."
Merrilyn W.Don't miss out! Price and availability may change
