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Greencastle Holiday Homes

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    Don't let other travellers get your favourite Greencastle area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Greencastle
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    The following rentals are within 30 kilometres of Greencastle.
    Washington House1 / 14
    (3)Excellent
    Sabillasville, MD
    7 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Waynesboro
    5 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    The Gatehouse at Loudon Forge1 / 15
    (5)Very good
    Fort Loudon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Happy Hen Loft at The Farmhouse1 / 16
    (1)Excellent
    Orrtanna
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Balcony
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 2017
    This location was perfect for our Gettysburg/Applefest weekend, it was close to everything. Very clean and charming. More than enough space for all 6 of us.
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    About this property
    Experience Gettysburg’s Historic sites and wine country living and discover the joy of staying in the entire upstairs at this historic 2 unit farmhouse with modern amenities just 10 minutes 7.4 miles from downtown Gettysburg. Enjoy the inviting, relaxing, and warm ambience of the entire upstairs...
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    Location Information
    Orrtanna, Pennsylvania 17353
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Sabillasville, MD
    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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    Location Information
    Sabillasville, Maryland 21780
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Sabillasville, MD
    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! Caboose Farm is a compound made up of three fully furnished homes. Totaling 14 bedrooms, the homes...
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    Location Information
    Sabillasville, Maryland 21780
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 11
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    Adams House1 / 13
    (1)Average
    Sabillasville, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 September 2016
    The house is generally a nice one with some major flaws. The internet they provided is really slow. We cannot use it to do anything. To maximize the use, there are four...
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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! 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 - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Fairfield
    5 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Parking
    • Internet Access
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rustic post and beam home rich with character. Five bedrooms and 2 full bath 2200 s/f sleeps up to 13. Cozy wood stove for heat with propane backup; a/c. House enjoys large yard and mature woodland surroundings. Relax on covered porch or large shaded deck and enjoy the biodiversity of your secluded...
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    Location Information
    Fairfield, Pennsylvania 17320
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 13
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    Fayetteville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is nestled in the foothills of the Appalachian's located about one mile from the Appalachian Trail. The house is recently remodeled with all amenities included, (linens, towels, paper products, dishes, etc.). We offer a gas fireplace, two full bathrooms (one upstairs and one down), a...
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    Location Information
    Fayetteville, Pennsylvania 17222
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sabillasville, MD
    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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    Location Information
    Sabillasville, Maryland 21780
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Rose Cottage Bed and Breakfast1 / 11
    (1)Excellent
    Fairplay, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Outdoor Dining Area
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2018
    Our host Kathy was just great. She gave us some great restaurant choices before we arrived at Rose Cottage. Once at RC, we were able relax in a very comfortable room and common...
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    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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    Location Information
    Fairplay, Maryland 21733
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    Lemasters
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Mountain Views
    • Porch
    • Parking
    • Air Conditioning
    • Outdoor Dining Area
    • Grill
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Parnell Springs Retreat is located in the Cumberland Valley near Mercersburg, Pa at the foot of Mt. Parnell. Located on a working farm, the newly renovated historic farmhouse sits quietly with spectacular views of the valley and surrounding mountains. The house is completely furnished and ready...
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    Location Information
    Lemasters, Pennsylvania 17252
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Orrtanna
    7 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Terrace
    • Patio
    • Washer
    • Central Heating
    • Grill
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This historic Farmhouse is over 100 years old with all modern amenities to make you stay in Gettysburg superb. Invite the whole family and spread out in 7 bedrooms with 8 beds plus two bathrooms, two living rooms, and two kitchens. The farmhouse sits on 1 large acre with plenty of room for the...
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    Location Information
    Orrtanna, Pennsylvania 17353
    Holiday Rental House - 7 Bedrooms, 2 Bathrooms, Sleeps 14
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    Orrtanna
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The General's Hideaway is a newly renovated vacation rental opened in late May of 2017 in Gettysburg's wine country. As you enter the General you will immediately feel welcomed by an expansive open floor plan spanning the living room with ample seating for your whole family along with a pool table...
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    Location Information
    Orrtanna, Pennsylvania 17353
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Carroll Valley
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay and enjoy this wonderful home inspired by Fixer Upper. We're 10 miles southwest of Gettysburg and minutes from Liberty Mountain Resort. You can hit the slopes, play a round of golf, enjoy the local wineries or tour the historical sites surrounding Gettysburg. On the weekends, enjoy the best...
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    Location Information
    Carroll Valley, Pennsylvania 17320
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sabillasville, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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...
    View all property information
    Location Information
    Sabillasville, Maryland 21780
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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