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

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Exceptional(12)

$566.06

Welcome to Woodhaven, your serene countryside escape nestled amidst 40 acresbrbrof tranquil landscapes. Originally built in the 1930s, this timeless farmhousebrbrhas been lovingly refurbished to seamlessly blend its historic charm withbrbrmodern comforts.brbrbrbrWith five spacious bedrooms and a fully finished basement living space,brbrCrimson Charm offers ample space to accommodate up to 13 guests, making itbrbrideal for family reunions, retreats, or gatherings with friends. Each roombrbrexudes warmth and character, providing a cozy haven for relaxation after a daybrbrof exploring the countryside.brbrbrbrStep outside and immerse yourself in the beauty of the sprawling estate.brbrWander through the lush forest, breathe in the fresh country air, or simplybrbrunwind on the expansive porch while taking in panoramic views of thebrbrsurrounding fields and forests.brbrbrbrFor those eager to explore, the property is located in Orange, Virginia, abrbrcharming small town nestled in the foothills of the Blue Ridge Mountains.brbrOrange offers a variety of attractions and activities for visitors, such asbrbrJames Madison's Montpelier, Historic Downtown Orange, vineyards and breweries,brbrShenandoah National Park, and local dining options.brbrbrbrWe recommend the following attractions:brbrbrbr- Montpelier (5 miles from property)brbrbrbr- Wolf Trap Farm (13 miles)brbrbrbr- Inn at Willow Grove (3 miles)brbrbrbr- Little Skyline Drive (2 miles)brbrbrbr- Skydive Orange (6 miles)brbrbrbr- Barboursville Vineyard (13 miles)brbrbrbr- Virginia Foothills Distillery (12 miles)brbrbrbrWhether you're seeking a peaceful retreat or a base for countrysidebrbradventures, Woodhaven invites you to experience the timeless allure of ruralbrbrliving in comfort and style. Book your stay today and discover the magic ofbrbrthis idyllic farmhouse getaway.brbrbrbrDogs only. Max 1 dog with additional fee + taxesbrbrbrbr

Woodhaven: Your Serene Countryside Escape by RedAwning

Orange, Virginia, United States

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Exceptional(17)

$277.7

pEscape to a newly renovated cabin, nestled in the tranquil woods at the northern edge of Lake Anna. Perfect for a serene retreat or a remote work getaway, this cozy haven offers stunning lake views and modern amenities to ensure a rejuvenating stay. Features a main level master. Gourmet kitchen with high-end appliances and granite countertops. Huge deck with view of the water. Rustic patio with campfire ring. Covered front porch with rocking chairs overlooking the woods. Peaceful. Quiet. Heaven/p

Calm Water Cabin Lake Anna

Orange, Virginia, United States

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$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

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$351.02

Nestled on 13.6 acres of exquisitely landscaped gardens & grounds, Boxwood Villa (circa 1891) is a hidden gem for a couple’s retreat. Named for its stunning boxwood bushes encircling the property, this historic home was thoughtfully renovated by Leslie Gregg, the founder of The Market at Grelen. Her keen eye for contemporary comfort & preservation of historic design breathes new life into this historic manor. For couples booking Boxwood Villa for a romantic getaway, all living spaces (living room, library, dining rooms) of the house are included as well as the kitchen and half bath. Room accommodations include the Primary Suite and full bathroom located on the first floor. Guests will have 100% privacy during the booking. All other bedrooms on the 2nd floor are excluded and will be locked. However, if you wish to rent an additional bedroom in the home, please email us for pricing. If you’d like access to all 5 bedrooms (accommodates up to 10 people), please see our other Boxwood Villa listing for access to the entire home. Complete and full access to the grounds, walking trail and the surrounding 13.6 acre parcel are exclusive to booked Boxwood Villa guests. IMPORTANT: Bookings are only confirmed after we receive an e-signature on The Boxwood Villa Housing Contract, via email. PLEASE NOTE: This listing is for the Primary Bedroom and downstairs (Kitchen, living rooms, dining rooms) and not the entire house. THIS LISTING IS ONLY AVAILABLE TO BOOK 30 DAY PRIOR TO CHECK-IN. There are no restrictions for booking the entire property. 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.

Villa

Luxurious Stay for 2 at Grelen's Enchanting Garden Estate: Boxwood Villa

Orange, Virginia, United States

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Exceptional(5)

$570.8

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

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Exceptional(9)

$621.56

You may never want to leave this 5-bedroom, 3-bath vacation rental located just a short distance from Lake Anna! Watch a movie on the 110 projector, swim day or night in the heated saltwater pool, and unwind in the 8-person hot tub under the stars. Grill or smoke your favorite meats, then kick back in comfort. If you're looking to venture, visit wineries on the Monticello Wine Trail or head to James Madison's Montpelier for guided tours, gardens, and walking trails. Book your next escape now!brbr-- THE PROPERTY --brbrDog Friendly w/ Fee | Community Boat Ramp | Private Heated Saltwater Pool (32'x16') | Game Room | Home TheaterbrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Twin/Full Bunk Bed w/ Twin Trundle | Bedroom 5: Twin/Full Bunk Bed w/ Twin TrundlebrbrINDOOR LIVING: 12 arcade games, pool table, 5 Smart TVs, board games, dining table & breakfast barbrOUTDOOR LIVING: Private hot tub (9'x9' XL 8-person hot tub), pool, beach area w/ hammocks, furnished deck, charcoal grill, fire pit, private yard (unfenced), kayaks, paddleboards, life vests, electric smoker brKITCHEN: Dishwasher, stove/oven, refrigerator, cooking basics, dishware & flatware, Keurig, Crockpot, toaster, trash bags & paper towelsbrGENERAL: Free WiFi, central A/C & heating, ceiling fans, linens & towels, in-unit laundry, dog kennel, keyless entrybrFAQ: Stairs required for access, 1st-floor bedroom & bathroom, pet fee (paid pre-trip)brPARKING: Driveway (6 vehicles), free street parking, RV/trailer parking allowed on-sitebrbr-- THE LOCATION --brbrLAKE ANNA: Frazers Lake POA boat ramp & docks (0.5 miles), The Boardwalk on Lake Anna (5 miles), Lake Anna State Park (9 miles)brAREA ATTRACTIONS: Downtown Orange (15 miles), James Madison's Montpelier (20 miles), Barboursville Ruins (25 miles), Shenandoah National Park (44 miles)brCHARLOTTESVILLE (~39 miles): Monticello, Virginia Discovery Museum, University of Virginia, John Paul Jones Arena, Ix Art ParkbrAIRPORTS: Charlottesville–Albemarle Airport (38 miles), Richmond International Airport (72 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/ $50 fee (+ fees & taxes, dogs only)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property requires stairs for accessbr- NOTE: This property is located just a few hundred yards from Lake Anna

Near Lake Anna: Gem w/ Saltwater Pool & Arcade!

Orange, Virginia, United States

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Bath

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$628.66

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!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

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Sleeps

$354.07

The Blenheim (Room #2) is a suite on the second floor of the historic Holladay House in downtown Orange, Virginia. Guests in the Blenheim will enjoy: There are three other guest rooms on the second floor of the house, as well as two on the walk-out basement level. Your hosts live in an innkeeper's suite on the first floor.brbrThe Blenheim and its attached sitting room overlook Main St., a perfect spot for watching the world go by. brbrFrom your windows, you can see the James Madison Museum, and the historic St. Thomas Episcopal Church.

The Blenheim Suite in historic Holladay House

Orange, Virginia, United States

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Most popular vacation rentals in Orange

$381.64

Guest house

The Biltmore Suite in historic Holladay House

Orange, Virginia, United States

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$248.18

Chapman on the Rail

Orange, Virginia, United States

Bed

Bath

Sleeps

$277.70

Calm Water Cabin Lake Anna

Orange, Virginia, United States

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Sleeps

$285.04

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The Fenton Room in historic Holladay House

Orange, Virginia, United States

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$311.17

One of Central Virginia's most historic Private Guest Residences

Orange, Virginia, United States

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$337.87

Rural and Spacious Virginia Home on ~ 2 Acres!

Orange, Virginia, United States

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Sleeps

$349.66

Guest house

The Edgcote Room in Historic Holladay House

Orange, Virginia, United States

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Sleeps

$354.07

The Blenheim Suite in historic Holladay House

Orange, Virginia, United States

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Bath

Sleeps

$764.51

Lake Anna Waterfront - Sleeps 21 - Dock for 3 Boats

Orange, Virginia, United States

Bed

Bath

Sleeps

$735.77