Chestertown, MD

Thornton Estates - Beautiful Manor House Situated on 300+ acers - Timeless Elegance

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12 guests
6 bedrooms
4 bathrooms
1000 sqft

Thornton Estates - Beautiful Manor House Situated on 300+ acers - Timeless Elegance

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Escape to the timeless elegance of Thornton Estate, a breathtaking 6,000-square-foot Manor House built in 1815, nestled just six miles from the charming town of Chestertown.
12 guests
6 bedrooms
4 bathrooms
1000 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM

  • Easy cancellation

About this property

Escape to the timeless elegance of Thornton Estate, a breathtaking 6,000-square-foot Manor House built in 1815, nestled just six miles from the charming town of Chestertown. Recently renovated to blend historic grandeur with modern luxury, this magnificent home offers an unparalleled retreat on 325 acres of picturesque traditional and organic farmland, complemented by 2,500 feet of serene shoreline along Morgan Creek. Immerse yourself in music with an Alexa-driven multi-room surround sound system and easily stay connected with underground fiberoptic high-speed internet, and . Timeless Elegance - Step into a world where classic architecture meets contemporary comfort. Thornton Estate boasts meticulously restored period details alongside state-of-the-art amenities, including a chef’s kitchen, formal dining room, elegant parlor, cozy living room, and a sophisticated library with a wet bar. Enjoy year-round relaxation on the summer and winter porches, savor your morning coffee or evening tea in the greenhouse, or take advantage of the private elevator for effortless access across the home. For a relaxing outdoor experience, dive into the private pool, take a stroll through the private vineyard or down the many walking trails exploring all the properties history, or pack a picnic and your fishing rods and enjoy the private bass pond. As a guest at Thornton Estate, you’ll enjoy exclusive access to the prestigious CRYCC Golf Club, perfect for a day on the fairways, For hunting enthusiasts, Thornton Estate offers *Hunter’s Specials, featuring guided hunting experiences on the expansive property. Thornton Estate invites you to create unforgettable memories in a setting that’s as captivating as it is luxurious. Book your stay and experience the timeless allure of this extraordinary estate. *Fees for the Hunter's Special and/or Any Events held on the property differ from standard nightly rates. Please contact us for pricing details on the Hunter's Special and Event bookings.

Escape to the timeless elegance of Thornton Estate, a breathtaking 6,000-square-foot Manor House built in 1815, nestled just six miles from the charming town of Chestertown. Recently renovated to blend historic grandeur with modern luxury, this magnificent home offers an unparalleled retreat on 325 acres of picturesque traditional and organic farmland, complemented by 2,500 feet of serene shoreline along Morgan Creek. Immerse yourself in music with an Alexa-driven multi-room surround sound system and easily stay connected with underground fiberoptic high-speed internet, and . Timeless Elegance - Step into a world where classic architecture meets contemporary comfort. Thornton Estate boasts meticulously restored period details alongside state-of-the-art amenities, including a chef’s kitchen, formal dining room, elegant parlor, cozy living room, and a sophisticated library with a wet bar. Enjoy year-round relaxation on the summer and winter porches, savor your morning coffee or evening tea in the greenhouse, or take advantage of the private elevator for effortless access across the home. For a relaxing outdoor experience, dive into the private pool, take a stroll through the private vineyard or down the many walking trails exploring all the properties history, or pack a picnic and your fishing rods and enjoy the private bass pond. As a guest at Thornton Estate, you’ll enjoy exclusive access to the prestigious CRYCC Golf Club, perfect for a day on the fairways, For hunting enthusiasts, Thornton Estate offers *Hunter’s Specials, featuring guided hunting experiences on the expansive property. Thornton Estate invites you to create unforgettable memories in a setting that’s as captivating as it is luxurious. Book your stay and experience the timeless allure of this extraordinary estate. *Fees for the Hunter's Special and/or Any Events held on the property differ from standard nightly rates. Please contact us for pricing details on the Hunter's Special and Event bookings.

About this property

Escape to the timeless elegance of Thornton Estate, a breathtaking 6,000-square-foot Manor House built in 1815, nestled just six miles from the charming town of Chestertown. Recently renovated to blend historic grandeur with modern luxury, this magnificent home offers an unparalleled retreat on 325 acres of picturesque traditional and organic farmland, complemented by 2,500 feet of serene shoreline along Morgan Creek. Immerse yourself in music with an Alexa-driven multi-room surround sound system and easily stay connected with underground fiberoptic high-speed internet, and . Timeless Elegance - Step into a world where classic architecture meets contemporary comfort. Thornton Estate boasts meticulously restored period details alongside state-of-the-art amenities, including a chef’s kitchen, formal dining room, elegant parlor, cozy living room, and a sophisticated library with a wet bar. Enjoy year-round relaxation on the summer and winter porches, savor your morning coffee or evening tea in the greenhouse, or take advantage of the private elevator for effortless access across the home. For a relaxing outdoor experience, dive into the private pool, take a stroll through the private vineyard or down the many walking trails exploring all the properties history, or pack a picnic and your fishing rods and enjoy the private bass pond. As a guest at Thornton Estate, you’ll enjoy exclusive access to the prestigious CRYCC Golf Club, perfect for a day on the fairways, For hunting enthusiasts, Thornton Estate offers *Hunter’s Specials, featuring guided hunting experiences on the expansive property. Thornton Estate invites you to create unforgettable memories in a setting that’s as captivating as it is luxurious. Book your stay and experience the timeless allure of this extraordinary estate. *Fees for the Hunter's Special and/or Any Events held on the property differ from standard nightly rates. Please contact us for pricing details on the Hunter's Special and Event bookings.

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Mar 7, 2026$1,025Available4
Mar 8, 2026$1,025Available4
Mar 9, 2026$1,025Available4
Mar 10, 2026$1,025Available4
Mar 11, 2026$1,025Available4
Mar 12, 2026$1,025Available4
Mar 13, 2026$1,025Available4
Mar 14, 2026$1,025Available4
Mar 15, 2026$1,025Available4
Mar 16, 2026$1,025Available4
Mar 17, 2026$1,025Available4
Mar 18, 2026$1,025Available4
Mar 19, 2026$1,025Available4
Mar 20, 2026$1,025Available4
Mar 21, 2026$1,025Available4
Mar 22, 2026$1,025Available4
Mar 23, 2026$1,025Available4
Mar 24, 2026$1,025Available4
Mar 25, 2026$1,025Available4
Mar 26, 2026$1,025Available4
Mar 27, 2026$1,025Available4
Mar 28, 2026$1,025Available4
Mar 29, 2026$1,025Available4
Mar 30, 2026$1,025Available4
Mar 31, 2026$1,025Available4
Apr 1, 2026$1,025Available4
Apr 2, 2026$1,025Available4
Apr 3, 2026$1,025Available4
Apr 4, 2026$1,025Available4
Apr 5, 2026$1,025Available4
Apr 6, 2026$1,025Available4
Apr 7, 2026$1,025Available4
Apr 8, 2026$1,025Available4
Apr 9, 2026$1,025Available4
Apr 10, 2026$1,025Available4
Apr 11, 2026$1,025Available4
Apr 12, 2026$1,025Available4
Apr 13, 2026$1,025Available4
Apr 14, 2026$1,025Available4
Apr 15, 2026$1,025Available4
Apr 16, 2026$1,025Available4
Apr 17, 2026$1,025Available4
Apr 18, 2026$1,025Available4
Apr 19, 2026$1,025Available4
Apr 20, 2026$1,025Available4
Apr 21, 2026$1,025Available4
Apr 22, 2026$1,025Available4
Apr 23, 2026$1,025Available4
Apr 24, 2026$1,025Available4
Apr 25, 2026$1,025Available4
Apr 26, 2026$1,025Available4
Apr 27, 2026$1,025Available4
Apr 28, 2026$1,025Available4
Apr 29, 2026$1,025Available4
Apr 30, 2026$1,025Available4
May 1, 2026$1,025Available4
May 2, 2026$1,025Available4
May 3, 2026$1,025Available4
May 4, 2026$1,025Available4
May 5, 2026$1,025Available4
May 6, 2026$1,025Available4
May 7, 2026$1,025Available4
May 8, 2026$1,025Available4
May 9, 2026$1,025Available4
May 10, 2026$1,025Available4
May 11, 2026$1,025Available4
May 12, 2026$1,025Available4
May 13, 2026$1,025Available4
May 14, 2026$1,025Available4
May 15, 2026$1,025Available4
May 16, 2026$1,025Available4
May 17, 2026$1,025Available4
May 18, 2026$1,025Available4
May 19, 2026$1,025Available4
May 20, 2026$1,025Available4
May 21, 2026$1,025Available4
May 22, 2026$1,025Available4
May 23, 2026$1,025Available4
May 24, 2026$1,025Available4
May 25, 2026$1,025Available4
May 26, 2026$1,025Available4
May 27, 2026$1,025Available4
May 28, 2026$1,025Available4
May 29, 2026$1,025Available4
May 30, 2026$1,025Available4
May 31, 2026$1,025Available4
Jun 1, 2026$1,025Available4
Jun 2, 2026$1,025Available4
Jun 3, 2026$1,025Available4
Jun 4, 2026$1,025Available4
Jun 5, 2026$1,025Available4

Amenities

Shower
Hair dryer
Shampoo
Bathtub
Fire place
TV
Air conditioning
Heating
Sound system

Amenities

  • Bathroom 1
      Shower
  • Bathroom 2
      Hair dryer
  • Bathroom 3
      Shampoo
  • Bathroom 4
      Bathtub
  • Living room
      Fire place
      TV
      Air conditioning
      Heating
      Sound system
      Ceiling fan
  • Common area
      Wifi
      Smoke detector
      Carbon monoxide detector
      First aid kit
      Fire extinguisher
  • Pool
      Pool outdoor
  • Kitchen
      Kitchen
      Dishwasher
      Microwave
      Oven
      Coffee maker
      Fridge
  • Laundry room
      Washer
      Dryer
      Iron
  • Office
      Dedicated workspace
  • Exterior
      Pet relief area
  • Garage
      Free parking
  • Patio
      BBQ Utensils
  • Garden
      Garden
  • Game room
      Game Room
  • Bedroom 1
      Hangers
  • Bedroom 2
      Crib
  • Bedroom 3
      Bed linens

Where you'll sleep

Bedroom 1
Bedroom 2
Bedroom 3
Bedroom 4
Bedroom 5
Bedroom 6

Explore Chestertown, MD

Immerse yourself in the historic charm and waterfront beauty of Chestertown, where storied landmarks meet the tranquil rhythm of Maryland’s Eastern Shore. Spend your afternoons exploring the town's historical places or wander through the vibrant Chestertown Farmers Market to gather local artisanal provisions for your stay. For coastal recreation, enjoy easy access to Wilmer Park and Chestertown Marina LLC, or take a short drive to Lockbri

Things to know

Here are some things which you should know before booking Thornton Estates - Beautiful Manor House Situated on 300+ acers - Timeless Elegance

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
12 guests maximum
Pets not allowed
No smoking - fees will apply
Events allowed with approval
Commercial photography requires approval

House rules

This home follows a strict maximum occupancy rule. Please make sure that the total number of guests accompanying you (including both children and adults) doesn't exceed the indicated maximum occupancy above to avoid cancellation of your stay and additional fees.

Cancellation policy

This property follows Tidewater Vacations’s standard cancellation policy.

Cancellation policy

1. Refundable Bookings
Cancellation Deadlines
• For stays under 15 nights, you may cancel or reschedule up to 14 days before check-in for a full refund. For stays 15 nights or longer, the cancellation window is 60 days.
• For some homes, a 30-day deadline applies — this will be clearly shown before you book.
• Cancellations must be submitted before 4 PM EST on the deadline day to qualify.
After the deadline - Fair-Refund policy
• If you cancel after the deadline:
• Tidewater Vacations will relist your dates and automatically refund you for any nights that rebook.
• The refund per night will be the lower of the original price or rebooking rate.
• Nights that do not rebook are non-refundable.
2. Non-refundable Bookings
• If you selected a Non-Refundable rate at checkout, the booking cannot be changed or canceled, and no refund will be issued.
3. Half-Now-Half-Later Bookings
• The first half of your payment is non-refundable.
• The second half may be refunded according to the standard cancellation policy.
4. Date Changes & Rebooking
• Once a stay is canceled, you can't rebook the same dates yourself.
• If you need help choosing new dates, our Concierge team is happy to assist.
5. Transfers to Another Guest
• You may transfer your booking to someone else at no charge.
• Just contact the Concierge with the new guest's name and email.
• The new guest must accept the transfer for it to take effect.
6. Policy Match Guarantee
• If a better price is available for the same property on Airbnb or the owner's site, contact the Concierge — Tidewater Vacations will match it.
Final Note
By completing your booking, you acknowledge and agree to Tidewater Vacations's cancellation policy.