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The Waterfront Retreat- With Sauna and Hot Tub!

Waterfront holiday home with kitchen and balcony

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Fridge, microwave, oven, stovetop - The Waterfront Retreat- With Sauna and Hot Tub! (Chestertown)
Fridge, microwave, oven, stovetop - The Waterfront Retreat- With Sauna and Hot Tub! (Chestertown)
Property grounds - The Waterfront Retreat- With Sauna and Hot Tub! (Chestertown)
Pool - The Waterfront Retreat- With Sauna and Hot Tub! (Chestertown)
Interior - The Waterfront Retreat- With Sauna and Hot Tub! (Chestertown)
At The Waterfront Retreat- With Sauna and Hot Tub!, you can look forward to a firepit, a garden and a sauna. Guests can connect to in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms4 bathrooms

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Parking available

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

The Waterfront Retreat- With Sauna and Hot Tub!

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.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Sauna

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3.5 bathrooms

Living spaces

  • Dining table

Entertainment

  • TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Garden

Laundry

  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • On the waterfront

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Garden

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The Tolhouse Short or Long-Term
  • Washing machine
  • Dryer
  • Air-conditioning
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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

437893

About the area

Located in Chestertown, this holiday home is on the waterfront. Rock Hall Harbor and Rolphs Wharf Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Eastern Neck National Wildlife Refuge and Chesapeake Bay. Visit our Chestertown travel guide
View more Holiday homes in Chestertown
Map
Chestertown, MD

What's nearby

  • Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.
    Washington College
    17 min drive - 20.9 km
  • The Mainstay
    13 min drive - 15.1 km
  • Rock Hall Harbor
    14 min drive - 15.8 km
  • Waterman’s Museum
    14 min drive - 15.5 km
  • Ferry Park
    15 min drive - 16.9 km

Getting around

  • Baltimore, MD (MTN-Martin State)
    125 min drive

Restaurants

  • Ford's Seafood
    13 min drive
  • Tolchester Marina Beach Bar
    16 min walk
  • Waterman's Crab House
    14 min drive
  • Harbor Shack
    15 min drive
  • Jellyfish Joel's
    26 min drive

Frequently asked questions

Is The Waterfront Retreat- With Sauna and Hot Tub! pet-friendly?

No, pets are not allowed at this property.

How much is parking at The Waterfront Retreat- With Sauna and Hot Tub!?

On-site parking is available at the property.

What time is check-in at The Waterfront Retreat- With Sauna and Hot Tub!?

Check-in begins at 4:00 PM.

What time is check-out at The Waterfront Retreat- With Sauna and Hot Tub!?

Checkout is at 10:00 AM.

Where is The Waterfront Retreat- With Sauna and Hot Tub! located?

Situated on the waterfront, this holiday home is steps away from Chesapeake Bay and Northern Chesapeake Bay. The Mainstay and Rock Hall Harbor are also within 9 miles (15 km).

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The Waterfront Retreat- With Sauna and Hot Tub! Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

10

Cleanliness

10

Location

Reviews

10/10 Excellent

Merrilyn W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 7 nights in Dec 2025