Vacation Rentals By Owner In Orange, VA

Step into a world of charm, class and European glamor at The Grelen Depot’s The 118 suite. Thoughtfully renovated and designed by Leslie Gregg, the founder of The Market at Grelen, this luxury suite is perfect for a romantic couples getaway or a charming stay during a wedding weekend. Located on Main Street in the historic town of Orange, Virginia, the Grelen Depot has been renovated to meet expectations for modern comforts as well as convenience.brbrThe suite includes a beautiful living space that includes a seating area, a desk and a small glass table for four ( perfect for cards!). There is a comfortable bedroom with a queen bed and a gorgeous bright white marble bathroom with a glass shower and gold fixtures. The original woodwork and wood floors add to the ambiance of this special spot!brbrGuests will have to type in a code and go upstairs (either by stairs or elevator) and the suite is at the end of the hall. The guests will have access to the living space, bedroom and full bath.brbrThe Events & Properties team from The Market at Grelen manages this property and is happy to help you before and during your trip.brbrThe 118 suite is located on Main Street in the historic town of Orange, Virginia. It is within walking distance of local boutique shops, antique stores, Taylor Park and several local restaurants. This town has much to offer visitors: James Madison’s Montpelier (10 mins away), The Market at Grelen (15 mins away) and Woodberry Forest School (10 mins away) as well as several local wineries and breweries in the area. In addition, Gordonsville, VA (10 minutes away) is another adorable Main Street town that is worth the visit.brbrPublic transportation is limited, and a car rental is recommended for getting around the area. The TOOT (Town of Orange Transit) provides limited public transportation around the town of Orange and to Gordonsville. Additionally, there are a variety of tour guides in the area for winery tours, etc. Ask us for recommendations or go to our community website: rural roots va dot com.brbrNote: We want our guests to know that this property is located within The Grelen Depot. The building is located right next to the railroad tracks so we offer ear plugs and a noise machine for light sleepers. There are trains that come thru the town during the night. Additionally, The Grelen Depot is an event venue so those renting the 118 might hear party noise until 11pm. We definitely try to keep noise to a minimum and quiet hours are from 11pm to 8am. We will make every effort to let those renting The 118 know if an event is taking place that night.

Luxury Suite at Grelen's Historic Depot

Orange, Virginia, United States

Bed

Bath

Sleeps

$349.66

The Edgcote (Room #5) is private room on the walk-out lower level of the historic Holladay House in downtown Orange, Virginia. Guests in the Edgecote will enjoy:brbr* Living in the 1910's portion of the housebr* Use of the recently redecorated common parlor, study, and dining room areasbr* A combination of historic decor and modern conveniencebr* Free off-street parkingbr* Walking distance to all sights in Orange, short driving distance to Montpelier, Monticello, Highland, wineries, and more!

Guest House

The Edgcote Room in Historic Holladay House

Orange, Virginia, United States

Bed

Bath

Sleeps

Exceptional(7)

$504.63

Welcome to your lakeside retreat at Lake Anna, Virginia! This spacious home sits on 2 acres and is perfect for families, large gatherings, or a romantic getaway. With 4 bedrooms and 3 bathrooms, it comfortably accommodates up to 11 guests. Enjoy the expansive outdoor space, great for outdoor activities, while the interior is stocked with games and entertainment for all ages. Experience the best of lakeside living!br**Sleeping Space:**brbr- Master Suite: King bed with an en-suite bathroom.br- Queen Bedrooms: Two queen bedrooms share a conveniently located bathroom.br- Bunk Room: 4 twin beds.br- Additional Sleeping: A pull-out couch in our basement TV room. The room has doors that enclose it to transform it into a private space for extra sleeping space.brbr**Bedroom Amenities:**brbr- Blackout curtainsbr- Sound machinesbr- Portable fansbr- Pack and play cribbr- Baby monitorbr- Scalebrbr**House Amenities:**brbr- Hot tubbr- Fire Pitbr- Kayaksbr- Paddleboardsbr- Life jacketsbr- Pool tablebr- Ping pongbr- Dart boardbr- Foosball tablebr- Interactive wall gamesbr- Fully equipped kitchenbr- Outdoor grillbr- Grill utensilsbr- Boat slip for easy lake accessbrbrYou will have exclusive access to the entire house, including all the amenities listed above. With the lake just a short walk away, indulge in fishing, boating, and other water activities at your leisure.br

Lake access w/hot tub, game room,boat slip, kayaks & more

Orange, Virginia, United States

Bed

Bath

Sleeps

Exceptional(12)

$1141.1

Nestled on 13.6 acres of exquisitely landscaped gardens and grounds, Boxwood Villa is a hidden gem for small group weekends, gatherings or accommodation for wedding guests. Named for its stunningly large boxwood bushes encircling the property, this historic home was lovingly and thoughtfully renovated by Leslie Gregg, the founders of The Market at Grelen. Her keen eye for contemporary comfort and preservation of historic design has breathed new life into this historic manor originally built in 1891. This 5-bedroom home is available for guests who want to enjoy a Virginia countryside weekend getaway or retreat. Boxwood Villa maintains a beautiful balance between old-world, historic charm and modern elegant flair. This gorgeous manor home has been designed with comfort in mind while also celebrating the exquisite architecture of the late 1800s. Each room is spacious with high ceilings and multiple windows, which allow natural light to pour in giving guests a sense of being embraced by the natural beauty of this special property. The living room and library have plenty of seating for intimate social gatherings while the two separated dining rooms collectively seat up to 18 guests making it a perfect place to host small dinner parties. The expansive 3rd floor is entirely open making it ideal for yoga and wellness retreats as well as conferences. Complete with a roll-out television for video viewing and presentations, the 3rd floor revolutionizes Boxwood Villa’s versatility and offerings to guests. Outdoor space: Within the 13.6 acres of cultivated gardens and grounds are several idyllic locations for a picnic beneath the shady canopy of trees. Surrounding the property is an easy ½ mile walking trail, perfect for stretching your legs and exploring nature. The Market at Grelen (located 8 minutes away) has additional trails to explore more of the Virginia countryside and natural beauty. IMPORTANT: Bookings are only confirmed after we receive an e-signature on The Boxwood Villa Housing Contract, via email. FOR WEDDINGS/EVENTS PLEASE VISIT OUR BOXWOOD VILLA WEBSITE AND SUBMIT AN INQUIRY THROUGH THERE. PETS: Pets (dogs only) are allowed with written permission and an extra fee of $200/per pet. SECURITY DEPOSIT: $1000.00

Villa

Grelen's Boxwood Villa: An Enchanting Estate with Beautiful Gardens

Orange, Virginia, United States

Bed

Bath

Sleeps

$226.98

Stay comfortably in Orange at this fully renovated 100-year-old 3-bedroom 2 bath craftsman cottage. It's bigger than it looks, double sized living room, formal dining room, new designer kitchen with custom cabinets and high-end appliances. A full laundry room is attached to the kitchen. First floor master suite has 1 queen bed, full bath and walk-in closet. Upstairs has two bedrooms, one with 2 twin beds, the other has a single day-bed with a trundle pullout. There is a second full bath upstairs with tub and shower. First floor has two heat pump systems that heat and cool, and oil radiant heat as back up. Upstairs has new baseboard heat and ac units. We're happy to assist with any questions while you stay at our terrific house.

Craftsman Cottage - Charming 3-bedroom house with WiFi and AC in lovely Orange

Orange, Virginia, United States

Bed

Bath

Sleeps

$650.8

Welcome to Sunset Cove at Lake Anna – Waterfront, Spacious & Perfect for Groups!brbrNestled along the tranquil shores of Lake Anna, Sunset Cove is a stunning, waterfront 5-bedroom, 3.5-bath retreat where modern comfort meets natural beauty. Designed with relaxation and togetherness in mind, this spacious home has everything you need for the perfect lake getaway — whether you’re hosting a family reunion, a friends' weekend, or simply escaping the everyday.brbrInside, you’ll find an immaculate, fully stocked kitchen with stainless steel appliances, stone countertops, and plenty of space for prepping and serving meals. The large dining area invites everyone to gather around for breakfast, dinner, or late-night board games.brbrEach of the five thoughtfully decorated bedrooms offers restful sleep with high-quality bedding, including 4 king beds, 1 queen bed, and a queen-over-queen bunk bed. And with a TV in every room, everyone can unwind on their own schedule.brbrThe spacious living room is perfect for lounging or entertaining, featuring plush seating and a pool table for friendly games and laid-back fun.brbrStep outside and soak in the true magic of Sunset Point — a beautiful patio with stunning lake views, perfect for grilling, dining al fresco, or watching the sunset melt into the water. The lush backyard leads directly to the water’s edge, where you’ll enjoy full access to a private pier—great for fishing, swimming, kayaking, or simply admiring the peaceful shoreline. Enjoy crackling fires by the lake and explore the water with complimentary kayaks (2 adult sizes and 2 youth sizes w/lifejackets)—perfect for adventure by day and relaxation by night. You also have access to the community ramp, if you choose to bring your boat!br*Life jackets are not provided in all sizes, so guests are asked to bring properly fitting life jackets for each member of their group. Please ensure they are in good condition and appropriate for water use.brbrFrom sunrise coffee on the patio to cozy evenings under the stars, Sunset Point offers more than just a place to stay — it’s a destination to be remembered.brbrPET FRIENDLY! This is a pet-friendly home. All guests will have a $500 refundable security hold placed on their visit, regardless of whether they bring a pet. If you are bringing a pet, there is an additional $100 non-refundable pet fee per pet. Please be sure to include your pets in your total guest count at booking—this will activate the pet fee. We allow up to 2 pets per stay. The $500 security hold covers any potential damage or soiling and will be refunded after checkout if no issues are found. *This is in addition to our Truvi protection. More info below.brbrImportant: Before you arrive, you will be asked to complete guest verification through third-party provider Truvi. This is done to ensure we are keeping up to date with short-term rental regulations as well as providing both our guests and our properties with extra protection. Truvi will contact you via email and/or text to complete the ID verification. Please do so prior to arriving at the property to enable a quick and easy check-in process. You will also be given the choice between a security deposit or a $35 non-refundable damage waiver.brbrMinimum age of primary renter is 25. The maximum number of guests is limited to 14 persons. The primary Guest booking the stay must stay for the entire duration of the booking dates, must also be the same Guest to complete the Renter's Agreement and the Truvi Guest Verification. Any restrictions or House Rules violated in the Renter's Agreement could incur charges to the Guest post stay or cause forfeit of the security deposit. For all bookings, check-in instructions will not be provided until the renter agreement is signed.brbrLinens & Bed SetupbrProfessionally cleaned linens are included with each reservation through a linen service fee. To ensure guests can clearly see that all linens are fresh and clean upon arrival, they are delivered and placed in the home but beds are not made. Guests are welcome to set up beds as they prefer.brbrTo help you settle in comfortably, we provide a basic set of starter supplies in each of our vacation rentals. These items are intended to cover your needs for the first day or so and may not be sufficient for the duration of your stay. Guests are responsible for supplying any additional items they may need during their stay.brbrPlease note that environmental factors can sometimes affect water clarity and recreational use, depending on severity and location. While we want all guests to enjoy their time at the lake, we cannot be responsible for their presence or any restrictions that may result. For the most up-to-date information on water conditions, we recommend checking local resources before and during your stay.

Sunset Cove Waterfront, Sleeps 14, Open concept

Orange, Virginia, United States

Bed

Bath

Sleeps

Exceptional(6)

$254.78

We must preapprove your booking. When you request to book please let us know why you are visiting the area.brbrUpscale boutique loft, would be great for a honeymoon suite or getting ready for an event! Unique and right on the rail road tracks! If you love trains and small towns this is the place. Building was originally built in 1908, and just underwent a major total renovation. Walk in the quaint historic downtown of Orange, one block off main street.brbrReserved parking spot goes with the space. Also, extra public parking spots adjoin the property and there is an electric car charger available when not in use by someone else.brbrSpace is not suitable for children or Pets.

Chapman on the Rail

Orange, Virginia, United States

Bed

Bath

Sleeps

Exceptional(15)

$371.52

Experience the historic Piedmont Region at this quiet Orange retreat. Perfectly located near Woodbury Forest School, premier wedding venues, live music, the Four County Players, and wineries. This spacious 3-bed, 3-bath home offers the best of Central Virginia. Enjoy day trips to Shenandoah, UVA, or DC. Relax on the screened porch, listen to the chorus of birdsong and cows lulling, and appreciate luxury touches like 100% cotton bedding. Your ideal Virginia escape awaits!brbr-- THE PROPERTY --brbrQuiet Neighborhood Location | 3,084 Sq Ft | ~30 Mi to Shenandoah National ParkbrbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin BedsbrbrOUTDOOR LIVING: Spacious yard, Adirondack chairs, patio furniture, wooded views, dining area, outdoor dishware, 2 covered porches, front sun porch, 2-acre lot, wildlife viewing, stargazing, rain umbrellas, large cooler, Ambient Weather station brINDOOR LIVING: 1 Roku Smart TV (personal log-in required), hardwood floors, office workspace, dining table, ceiling fans, mudroom, breakfast nookbrKITCHEN: Granite countertops, dishwasher, microwave, drip coffee maker, electric kettle, electric stovetop, blender, mixer, toaster, cooking basics, dishware & flatware, complimentary starter kit (coffee & tea)brGENERAL: Free WiFi, central heating & air conditioning, washer & dryer, laundry detergent, linens & towels, complimentary toiletries, hair dryers, iron & board, new mattressesbrFAQ: Stairs required to enter & to access all bedrooms, quiet hours (Sun-Thurs 8:00 PM-7:00 AM, Fri-Sat 10:00 PM-9:00 AM), 3 Wyze doorbell camera (facing out)brPARKING: Garage (1 vehicle), driveway (2-3 vehicles)brbr-- THE LOCATION --brbrHISTORY: James Madison's Montpelier (7 miles), The Exchange Hotel Civil War Hospital (11 miles), Barboursville Ruins (15 miles), Monticello (30 miles)brHOT SPOTS: Montpelier Races (6 miles), The Market at Grelen, (7 miles), Woodberry Forest School (7 miles), Four County Players (14 miles), Charlottesville Downtown Mall (30 miles), University of Virginia (32 miles), Grand Caverns (54 miles), Luray Caverns (56 miles)brWINERIES (surrounding area): Early Mountain Vineyards, Barboursville Vineyards, Keswick Vineyards, Horton Vineyards, Honah Lee Vineyard, Merrie Mill Farm and Vineyard, Burnley Vineyard, Chestnut Oak VineyardbrNATURE: The Montpelier-Grelen Hiking Trail (7 miles), Preddy Creek Trail Park (20 miles), Shenandoah National Park (29 miles), Ragged Mountain Nature Area (36 miles)brNEARBY TOWNS: Gordonsville (11 miles), Culpeper (20 miles), Charlottesville (30 miles), Fredericksburg (38 miles), Richmond (77 miles), Washington D.C. (88 miles)brAIRPORT: Charlottesville–Albemarle Airport (25 miles), Dulles International Airport (73 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking or vapingbr- No pets allowedbr- No events, parties, or large gatheringsbr- No food or drink on bedroom level (except water)br- No burning candles or flamesbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to enter and to access all bedroomsbr- NOTE: Please observe quiet hours as follows: Sunday-Thursday 8:00 PM to 7:00 AM; Friday-Saturday 10:00 PM to 9:00 AMbr- NOTE: This property is on a septic system; please be kind and flush nothing but toilet paperbr- NOTE: The cleaning fee includes prep services for each guest's fresh linens and towelsbr- NOTE: Your safety matters. This property features 3 Wyze Doorbell devices with exterior security cameras located at the front, rear, and side exterior doors facing the outdoor entryways. The cameras do not look into any interior spaces. The cameras record video and sound when motion is detected by the device or when the video doorbell button is pressed

Rural and Spacious Virginia Home on ~ 2 Acres!

Orange, Virginia, United States

Bed

Bath

Sleeps

Exceptional(104)

$313.85

This is your opportunity to spend a weekend at one of the most historic and private homes in Orange VA. This is the former residence of James Madison’s brother Ambrose Madison est 1783. The estate features 50+ acres of open fields and stream, 3 private ponds, walking trails, gorgeous sunset views, and was featured on the 2012 Garden Club of Virginia Historic Garden Week Tour.br brCome experience the country side in this modern guest cottage. Complete with full kitchen, 2 bedrooms featuring a king size bed downstairs and 2 twin beds upstairs, 2 full bathrooms with walk in shower, living room, screened in porch, patio, private parking, and media area with cable TV. The cottage will sleep four very comfortably, over 1000+ square feet. brbrMinutes from Woodberry Forest School and downtown Orange, 8 Minutes to best main street in VA Gordonsville, 25 minutes from Charlottesville, UVA and Scott Stadium, this is an ideal setting for a private getaway. The property has a central location in the up and coming Virginia Wine region; quickly becoming the Napa Valley of the east coast. Property has great fishing in the private ponds, manicured grounds, guided hunting, golf outings, and Wine Tours. The owners are local and can serve as great advisers and historians of the area. There are many local museums such as Montpelier, civil war battlefields, restaurants, antiquing and history to explore. brWant to live on the wild side Orange offers the opportunity to go sky diving! We look forward to your visit.

One of Central Virginia's most historic Private Guest Residences

Orange, Virginia, United States

Bed

Bath

Sleeps

Very Good(1)

$105.66

Stay comfortably in Orange at this phenomenal mastser room. Rest easy in the king bed after a day of exploring. Enjoy the convenience of amenities like AC, iron, and a hair dryer. Our place will help you feel at home while you're traveling in Orange. Right on the lake with a two story dock, beach, four kayaks and paddleboard. Boat house has full electric, rafts and life jackets and much more. Fire pit overlooking the lake. This is on the main floor of the lake house and only two rooms on the main floor plus the entertainment room large dining room and kitchen with two full size refrigerators with freezers and ice maker, hot and cold water dispenser, small beverage refrigerator.

Marvelous Master on the Water at Lake Anna with Tv and Full Bathroom

Orange, Virginia, United States

Bed

Bath

Sleeps

$234.59

Escape the demands of daily life and enjoy the seclusion and privacy of this 2-bedroom, 1-bath vacation rental in Orange, VA! Perfect for a romantic retreat or a small group getaway, this cozy cottage offers a fully equipped kitchen, a modern interior, and close proximity to Lake Anna. When you’re not out on the water, explore the on-site hiking trails or visit James Madison's Montpelier. After a day of adventure, sip a glass of wine on the front porch or unwind with a movie on the Smart TV.brbr-- THE PROPERTY --brbrPet Friendly w/ Fee (2 Max) | Furnished Porch | Free WiFi | Private Trail System On-SitebrbrBedroom 1: Queen Bed | Bedroom 2: Queen BedbrbrMAIN FEATURES: Smart TV w/ cable, modern furnishings, ceiling fans, picnic tablebrKITCHEN: Cooking basics, microwave, refrigerator, stove/oven, dishwasher, Keurig coffee makerbrGENERAL: Linens/towels, central A/C, electric heating, in-unit washer/dryer, hair dryer, hangers, complimentary toiletriesbrFAQ: Pet fee (paid pre-trip), 2 exterior security cameras (facing out), fragile antiques brACCESSIBILITY: 3 steps required to enter, single-story homebrPARKING: Driveway (4 vehicles), RV/trailer parking allowed on-sitebrbr-- THE LOCATION --brbrFUN ON THE WATER: Lake Anna (1 mile), The Boardwalk on Lake Anna (4 miles), Lake Anna State Park (8 miles), Swim Beach at Lake Anna State Park (11 miles)brLOCAL ATTRACTIONS: Downtown Orange (14 miles), James Madison's Montpelier (19 miles), Barboursville Ruins (25 miles), Fun Land of Fredericksburg (33 miles), Shenandoah National Park (43 miles)brCHARLOTTESVILLE (~45 miles): Monticello, Virginia Discovery Museum, University of Virginia, John Paul Jones ArenabrAIRPORTS: Charlottesville–Albemarle Airport (40 miles), Richmond International Airport (71 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $75 fee (+ fees & taxes, 2 pets max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This single-story property requires 3 steps to enterbr- NOTE: This property may not be suitable for young children due to the fragile antiques on-site, which could pose a safety risk if brokenbr- NOTE: Your safety matters. This property features 2 exterior security cameras: 1 camera is located in front of the house facing the entrance, and 1 camera is near the front yard facing the driveway. The cameras do not look into interior spaces. The cameras record video and sound when activated by motion. They will record when they first sense motion and 30 seconds after the last motion is detected

Cottage

Orange Cottage w/ Hiking Access: 1 Mi to Lake Anna

Orange, Virginia, United States

Bed

Bath

Sleeps

Most popular vacation rentals in Orange

$1141.10

Villa

Grelen's Boxwood Villa: An Enchanting Estate with Beautiful Gardens

Orange, Virginia, United States

Bed

Bath

Sleeps

$1.00

Crescent Cove: Luxury Lake Anna Retreat for 18 with Sandy Beach & Hot Tub

Orange, Virginia, United States

Bed

Bath

Sleeps

$254.78

Chapman on the Rail

Orange, Virginia, United States

Bed

Bath

Sleeps

$291.80

Calm Water Cabin Lake Anna

Orange, Virginia, United States

Bed

Bath

Sleeps

$313.85

One of Central Virginia's most historic Private Guest Residences

Orange, Virginia, United States

Bed

Bath

Sleeps

$349.66

Guest house

The Edgcote Room in Historic Holladay House

Orange, Virginia, United States

Bed

Bath

Sleeps

$349.66

The Blenheim Suite in historic Holladay House

Orange, Virginia, United States

Bed

Bath

Sleeps

$371.52

Rural and Spacious Virginia Home on ~ 2 Acres!

Orange, Virginia, United States

Bed

Bath

Sleeps

$735.77

Lakeside Retreat with Private Dock w/ Kayaks and Paddle-boards! Boat Slip too!

Orange, Virginia, United States

Bed

Bath

Sleeps

$702.82