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Cottage on Beautiful Wooded Waterfront Farm- 'Chestnut House'

Bedrooms 2
Property type cottage
Minimum Stay 3 nights


About the property

Cottage, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 4-6)

Cozy, comfortable new cottage on 135-acre farm in Annapolis, Maryland available for short or long-term stays. Perfect for individuals, couples or families seeking a convenient and wonderful getaway. The cottage is on a one-acre lot quite separate from the other homes on the farm.

This is a very special home on one of the largest pieces of privately-owned conservation land in Maryland, with a wealth of wildlife and gorgeous views of the water, woods, and fields. You will feel rejuvenated and relaxed after a stay here-- relax by the fire, go for walks or runs in the woods, sleep soundly in the great beds. (Or, if you have to, you can work on your laptop with the free wireless internet.) It feels like a real getaway while being so close to town.

Renters are given access to the farm trails and creek: perfect for hiking, jogging, fishing, kayaking (bring your own), cross country skiing. Only 10 minutes to downtown Annapolis, 45 minutes to Washington DC and 35 minutes to Baltimore. Perfect base for visiting historic downtown Annapolis, the US Naval Academy, and St. John's College; for shopping at the malls and outlets; and for making day trips to the Eastern Shore, Baltimore museums, and Washington sightseeing. Sandy Point State Park beach and playground are 4 miles away. Only 10 minutes to Anne Arundel Medical Center, if needed!

The cottage has a full modern kitchen, washer/dryer, fireplace and plenty of firewood, 2 bedrooms, 2 full baths, office nook. Queen bed in one bedroom, two twin beds in the second, queen Pottery Barn sleep sofa in downstairs living area and one single cot. The large deck has a charcoal grill and outdoor furniture. The living and eating areas have beautiful new wood floors and a wall of windows facing the woods and the creek beyond.

Great for all ages, baby and child equipment available (high chair, pack-n-play, children's plates/cups/cutlery). Forced air heat and central AC. Verizon FIOS TV and wireless internet included.

Keywords: Waterfront, cottage, cabin, woods, kids, pets, country, U.S. Naval Academy, St. John's College, Baltimore, Washington DC, historic, tourism.

More Details


Annapolis Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
  • Housekeeper Optional
House Rules:
  • Max. occupancy: 6
  • pets considered
  • children welcome
  • non smoking only
Location Type:
  • Rural
  • Water View
  • Waterfront
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Iron & Board
  • Linens Provided
  • Parking
  • Parking Off Street
  • Parking for RV/Boat/Trailer
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Wood Fireplace
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • 2 Bedrooms, Sleeps 6
  • Queen size Beds (1), Twin or Single Beds (1), Baby Cribs (1), Queen Sleep Sofa (1)
  • Books
  • DVD Player
  • Games
  • Music Library
  • Satellite / Cable
  • Television
  • Toys
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
  • ruins
  • synagogues
  • theme parks
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • boating
  • miniature golf
  • outlet shopping
  • photography
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • hiking
  • kayaking
  • mountain biking
  • pier fishing
  • sailing
  • sound/bay fishing
  • swimming
  • tennis


Exceptional! 5/5 -
(30 traveler reviews)

96% Complete
3% Complete
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Cottage on Beautiful Wooded Waterfront Farm- 'Chestnut House'
average rating of 4.9666667 based on 30 reviews

USNA Parents' Weekend

  • 5 of 5

We came for 2/C Parents' Weekend and it was Perfect!!! Cottage was just as beautiful and homey as the pictures showed. On a working FARM!!! Fabulously equipped kitchen. Plenty of towels, blankets, pillows. Easy commute from BWI, even after dark. Plenty close to DTA and USNA. We all loved it and will be back in 2018, unless we can find an excuse to come back sooner!!! After family went back home, I stayed and my girl friends came up for the rest of the week. Perfect girl's getaway.

  • Submitted: Oct 19, 2016
  • Stayed: October 2016
  • Source: VRBO, from HomeAway
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Chestnut House

  • 5 of 5

Our recent stay at Chestnut House was wonderful. The location is quiet and calming. The house has so many amenities that we didn't realize would be there. The inside is so spacious and the kitchen is so equipped. We had a 6 month old baby and a small pet and it met all our needs. The location is close to Rt. 50, Bay Bridge and Annapolis. With restaurants and grocery close by it is perfect. Would love to stay there again!

  • Submitted: Sep 12, 2016
  • Stayed: August 2016
  • Source: VRBO, from HomeAway
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Northern Virginia

Loved it - again!

  • 5 of 5

We've stayed at Chestnut House for 3 summers in a row and it was just perfect, again! My son now refers to it as "home during the summer." We love the quiet and calm - I can really feel myself relax as I drive up the driveway. Our hosts and the farm manager were super - very attentive and helpful. Close to downtown Annapolis and the Naval Academy. We love everything about it, and hope to be back next year!

  • Submitted: Jul 20, 2016
  • Stayed: June 2016
  • Source: VRBO, from HomeAway
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Chapel Hill, North Carolina

Quiet Retreat close to Annapolis

  • 5 of 5

At the end of a busy day in Annapolis or the Eastern Shore, there's nothing better than returning to a secluded, peaceful place to relax. Chestnut House is a great place to do just that ! And it's close to excellent restaurants ( Cantler's Crab House - fantastic ) and convenient shopping also. We highly recommend this very nice cottage to anyone who wants to be close to town and the USNA. Our reservation was handled by Kathy efficiently and completely, no problems at all on either end of our stay. We will definitely stay here again when we visit the area next time !

  • Submitted: Nov 23, 2015
  • Stayed: November 2015
  • Source: VRBO, from HomeAway
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Great Getaway!

  • 5 of 5

Wonderful getaway!

  • Submitted: Aug 5, 2015
  • Stayed: July 2015
  • Source: VRBO, from HomeAway
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Wonderful location, tasteful, comfortable and quiet

  • 5 of 5

This cottage is one of the best places in which we have stayed, if not the best. It is very comfortable with high quality furnishings and linens. It also has very interesting art in every room. The woodland setting is lovely and the farm is a delight.

We experienced a personal difficulty while we were staying and the hosts were gracious and very helpful to us in resolving the problem.

We will be returning to this jewel of a cottage soon.

  • Submitted: Jul 1, 2015
  • Stayed: June 2015
  • Source: VRBO, from HomeAway
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Property Manager

Property Manager
Member since: 2010
Speaks: english, french, spanish
Response time:
Within a day
Response rate:
Calendar last updated:
September 13, 2017

About The Owner

Our family has been in Annapolis for four generations.

The Owner purchased this cottage in 2008

Why The Owner chose Annapolis

This farm has been in our family for years. It's a peaceful place to relax, but close to our jobs and schools in the city. We've enjoyed making Chestnut House into a cozy place for getaways and holidays. The gorgeous wood flooring is made from trees that fell on the property. We also have sheep and border collies and chickens on the farm.

What makes this cottage unique

By renting this cottage, which is placed on a one acre plot quite separate and private from the other farm houses, you are also given access to the surrounding farm and woods owned by our family. While we ask renters to be respectful of this property and the wildlife on it, it is an amazing and unique place that we'd love to share with you.


Nearest Airport
23 Miles
Nearest Train
23 Miles
BWI station
Nearest Motorway
1 Miles
Route 50/301
Nearest Beach
5 Miles
Sandy Point
Nearest Point of Interest
Sandy Point State Park
Nearest Point of Interest
U.S. Naval Academy
Nearest Point of Interest
Navy-Marine Corps Stadium
Nearest Point of Interest
Entrance to Hollywood Farm


Rates & Availability

Taxes and fees are additional
This calendar has not been updated in over 2 months and the availability shown may not be accurate.

Additional information about rental rates

Effective March 1, 2016: Three night minimum= $900; $2100 per week.
USNA Commissioning Week and Boat Show rate: $2500/week.
Please inquire for monthly rates and boat mooring.

Security deposit due upon reservation. Payment of Rental Fee is due 30 days prior to check-in. Paypal and checks accepted. All payments in US Dollars please.
Cancellation policy: 100% if cancelled at least 90 days prior to the Check-in Date; 50% if cancelled 31 to 89 days prior to the Check-in Date; 0 % if cancelled 30 days or less prior to the Check-in Date

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.