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Middletown Holiday Homes

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    Don't let other travellers get your favourite Middletown area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 24 Rentals in Middletown
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    The following rentals are within 30 kilometres of Middletown.
    RIVERKEEPER INN, Waterfront Cottage on the Potomac1 / 27
    (10)Excellent
    Harpers Ferry, WV
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Two Rivers Guest House. Walk to rivers, parks, downtown and restaurants1 / 15
    (5)Very good
    Harpers Ferry, WV
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Adams House1 / 13
    (1)Average
    Sabillasville
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Adventure Inn - Historic Home with Hot Tub, close1 / 38
    (12)Excellent
    Harpers Ferry, WV
    4 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Internet Access
    • Mountain Views
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Wonderful place to stay. Clean and comfortable. Plenty of room to stretch out and relax. Our Harpers Ferry vacation was a blast!
    Reviewed 21 February 2017
    Adventure Inn was a wonderful place for our annual girls weekend get-away. Booking was simple and efficient. Check in was a breeze, with Chase, at the River Riders office, super...
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    About this property
    Historic 4 bedroom home just outside of Harpers Ferry, West Virginia convenient to all Harpers Ferry, Charles Town, and Shepherdstown attractions. Just an hour from the Washington DC and Baltimore, MD beltways; 1 hour from Fairfax, Virginia (VA); relax amidst the Blue Ridge Mountains near...
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    Harpers Ferry, West Virginia 25425
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 14
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    Fairplay
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Balcony
    • Outdoor Dining Area
    • Air Conditioning
    • Satellite TV
    • Private Garden
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the serenity of our captivating garden cottage, set in the beautiful Hagerstown Valley in Western Maryland. We're an excellent home base for local travel to Antietam National Battlefield and the C&O Canal in Shepherdstown, West Virginia, Our guests enjoy a private entrance that leads...
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    Fairplay, Maryland 21733
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Washington House1 / 14
    (3)Excellent
    Sabillasville
    7 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Internet Access
    • Porch
    • Parking
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 2015
    Our time at the Cabbose Farm in the "Washington House" was very special. The house was very spacious and inviting for us and our friends. The quietness of the grounds...
    Reviewed 9 April 2014
    My wife, mother in law, 2 yo, and I stayed at the Main House on the beautiful property in March. The house was amazing. Whereas the house appeared to be on the older side, the...
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    About this property
    Do you have a large family that wants to vacation together in a beautiful location in the mountains? Or do you need a scenic location for a wedding or corporate retreat? Then this is your solution!<BR><BR>Caboose Farm is a compound made up of three fully furnished homes. Totaling 14 bedrooms, the...
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    Sabillasville, Maryland 21780
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 16
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    Catoctin Valley Country Apartment1 / 8
    (4)Excellent
    Lovettsville, VA
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    • Air Conditioning
    • Shared Garden
    • Satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 2015
    My husband and I rented this apartment within a family home for a long weekend. It is very private; the family was not home that weekend, though, so can't speak entirely to this...
    Reviewed 4 June 2015
    Very clean and modern apartment. New appliances and comes with washer and dryer!Roberta was great in welcoming us and making sure we had everything we needed. Location is on...
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    About this property
    This beautiful 1 bedroom apartment is located in the heart of Loudoun County's Wine Region. It is situated on a scenic country road with it's own private entrance. It has a full kitchen, wifi, satellite TV and washer/dryer. A perfect getaway!<BR><BR>Guests will have access to their own private...
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    Lovettsville, Loudoun County 20180
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Gorgeous Mountain Views - Walk to historic town1 / 5
    (2)Excellent
    Harpers Ferry, WV
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • Satellite TV
    • Mountain Views
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2016
    The house was well maintained and looks out to the mountains, as advertised. The owner was very helpful. We had a great time.
    Reviewed 5 October 2015
    This vacation was absolutely perfect and that is no small part to Jacki and this amazing rental. We only had a small window of time to enjoy the rental and wanted to arrive...
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    About this property
    The Space<BR><BR>Enjoy your stay in our family home in Harpers Ferry. This house is well furnished, comfortable, open space overlooks mountains and river. <BR><BR>House is suitable for couples, families with children, group of friends.<BR><BR>Private driveway to accommodate 1 car. There is guest...
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    Location Information
    Harpers Ferry, West Virginia 25425
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Shepherd's Cottage at WeatherLea Farm1 / 15
    (2)Excellent
    Lovettsville, VA
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Internet Access
    • Balcony
    • Outdoor Dining Area
    • Terrace
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 November 2016
    This cottage was perfect for my three friends and I for the weekend. The cottage has all the modern conveniences you could want and still maintains a quaint cottage feel. The...
    Reviewed 24 July 2015
    Myself and 5 friends shared this wonderful cottage for the weekend. Everything that we needed was there! A Grill, cleaning supplies, the towels and linens were better than mine...
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    About this property
    Spend a relaxing vacation or weekend at our charming and newly-renovated cottage on a historic farm in Loudoun County, Virginia. On our farm we raise sheep, grow wine grapes, host weddings and accommodate overnight guests in two cottages. (Our other cottage, the Milk Cottage, sleeps up to 4 in...
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    Location Information
    Lovettsville, Loudoun County 20180
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Sabillasville
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Mountain Views
    • Porch
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Do you have a large family that wants to vacation together in a beautiful location in the mountains? Or do you need a scenic location for a wedding or corporate retreat? Then this is your solution! Caboose Farm is a compound made up of three fully furnished homes. Totaling 14 bedrooms, the homes...
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    Sabillasville, Maryland 21780
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Sabillasville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Do you have a large family that wants to vacation together in a beautiful location in the mountains? Or do you need a scenic location for a wedding or corporate retreat? Then this is your solution! Caboose Farm is a compound made up of six fully furnished homes. Totaling 24 bedrooms, the homes...
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    Sabillasville, Maryland 21780
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sabillasville
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Patio
    • Mountain Views
    • Porch
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Do you have a large family that wants to vacation together in a beautiful location in the mountains? Or do you need a scenic location for a wedding or corporate retreat? Then this is your solution!<BR><BR>Caboose Farm is a compound made up of three fully furnished homes. Totaling 14 bedrooms, the...
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    Location Information
    Sabillasville, Maryland 21780
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 11
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    Lovettsville, VA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Satellite TV
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A perfect getaway! This beautiful home is located in the heart of Loudoun County's Wine Region. It is situated on a scenic country road and has a full kitchen, WiFi, satellite TV and washer/dryer. Guests will have access to their own private outdoor space. Enjoy an afternoon nap in the hammock...
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    Location Information
    Lovettsville, Loudoun County 20180
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cantuta Inn Bed & Breakfast - Shallows Room1 / 4
    (5)Excellent
    Harpers Ferry, WV
    4 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Central Heating
    • Patio
    • Mountain Views
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 April 2017
    I would highly recommend a stay at Cantuta. From the moment we arrived we were graciously welcomed by Ethel and Rock. We enjoyed conversations with both Etel (about her native...
    Reviewed 20 March 2017
    We found the Cantuta Inn B & B to be very accommodating and it help make our stay in WV very pleasant. We enjoyed Etel and Rock. They were both very knowledgeable about the...
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    About this property
    Named for a colorful red flower that grows in the mountains of Etel's native Peru, the Cantuta Inn is a modern Bed & Breakfast in historic Harpers Ferry. Visit historic Harpers Ferry and take a break from the hectic pace of the modern world. Travel back in time to the Civil War era, or treat...
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    Location Information
    Harpers Ferry, West Virginia 25425
    Private Room - 4 Bedrooms, 1 Bathroom, Sleeps 4
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    Waterford, VA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Loudoun Valley Manor (Bed and Breakfast) offers several cozy bedrooms in a luxurious house conveniently located a quarter mile off Route 9, in the outskirt of Waterford, between Leesburg and Purcellville in Loudoun County, Virginia. Wonderful serene views of surrounding landscape. Each room has a...
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    Location Information
    Waterford, Loudoun County 20197
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Harpers Ferry, WV
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy historic Harpers Ferry and the Appalachian Trail. Marbrun House is within walking distance of lower historic downtown and you can be on the Appalachian Trail within minutes. This private entrance bed and bath includes coffee/tea service, refrigerator and microwave. We also offer shuttle...
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    Location Information
    Harpers Ferry, West Virginia 25425
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Turquoise room at Loudoun Valley Manor - near Leesburg off Route 91 / 15
    (2)Excellent
    Waterford, VA
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Housekeeping Included
    • Terrace
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Olga gave us a warm and friendly welcome; our visit was more like visiting an old friend than simply a host at a bed and breakfast. The Turquoise room, and the whole manor, was...
    Reviewed 26 May 2017
    Loudon Valley Manor is a wonderful place to stay--clean, spacious, and nicely decorated. Olga is an outstanding host. Our party of six greatly enjoyed our stay in this beautiful...
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    About this property
    Loudoun Valley Manor (Bed and Breakfast) offers several cozy bedrooms in a luxurious house conveniently located a quarter mile off Route 9, in the outskirt of Waterford, between Leesburg and Purcellville in Loudoun County, Virginia. Wonderful serene views of surrounding landscape. Each room has a...
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    Location Information
    Waterford, Loudoun County 20197
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Sienna Room at Loudoun Valley Manor - off Route 9 near Leesburg1 / 16
    (1)Excellent
    Waterford, VA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Parking
    • Private Garden
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    Olga made us feel at home in this beautiful house. The room was very nice and comfortable. Breakfast was awesome. We had a blast, lots of fun stuff to do in the area. I would...
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    About this property
    Loudoun Valley Manor (Bed and Breakfast) offers several cozy bedrooms in a luxurious house conveniently located a quarter mile off Route 9, between Leesburg and Purcellville in Loudoun County, Virginia. Stay for business or leisure! The property is located on a 6-acre lot and is in the midst of...
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    Location Information
    Waterford, Loudoun County 20197
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Frederick
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Secure Parking
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Washer
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come & Escape The Stresses Of Everyday Life And Enjoy A Little Piece Of Paradise. Be among the first to stay in this newly offered and beautifully decorated home, furnished with unparalleled elegance and style. A long tree lined private driveway leads to five acres of absolute paradise....
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    Frederick, Maryland 21703
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Sabillasville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Do you have a large family that wants to vacation together in a beautiful location in the mountains? Or do you need a scenic location for a wedding or corporate retreat? Then this is your solution! Caboose Farm is a compound made up of six fully furnished homes. Totaling 24 bedrooms, the homes...
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    Location Information
    Sabillasville, Maryland 21780
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shepherdstown, WV
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A charming three-bedroom home in historic downtown Shepherdstown, WV, with all of the modern amenities. Enjoy the convenience of walking to the local restaurants, art galleries, and antique shops. Stroll across the street to visit the Opera House or Shepherd University. All sorts of outdoor...
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    Location Information
    Shepherdstown, West Virginia 25443
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Frederick
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Balcony
    • Terrace
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This historic building situated in the heart of historic downtown Frederick was built in 1786. It is a two story brick house, which was used throughout it's history commercially on the first floor, where currently a wine shop operates. The second floor has always been used for residents, in former...
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    Frederick, Maryland 21701
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Clarksburg
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Satellite TV
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a gorgeous brand new Townhouse with one person living there. There is a vacant bedroom for temporary rental. Rental can be 3, 6, 9 months or case by case basis. Non-smoking home. The location is 2 minutes from I270 Highway and minutes from restaurants, bars, and shops like Target, Home...
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    Clarksburg, Montgomery County 20871
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 1
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    Frederick
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Mountain Views
    • Washer
    • Patio
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you like the show Fixer-Upper, you'll love the Uptown Cottage! Near Downtown Frederick, great restaurants, beautiful parks, historic sites and shopping. Less than an hour from Baltimore and Washington DC. Fully renovated, a great space for relaxing when you are not out and about. You'll enjoy...
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    Location Information
    Frederick, Maryland 21701
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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