68+ Vacation Rentals Near James Madison's Montpelier |
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  3. Charlottesville
  4. James Madison's Montpelier

Sailings Canada - Vacation Rentals in James Madison's Montpelier

Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm From US $475
         

9.6 (30 Reviews)
House
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
  • Air Conditioner
  • Parking
  • Pet Friendly

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Art House on Main From US $350
         

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10.0 (1 Review)
House
Art House on Main
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

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Mayhurst Inn From US $301
         

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9.2 (290 Reviews)
Bed & Breakfast
Mayhurst Inn
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Rustic Luxury Near Charlottesville/Montpelier/Wineries/A Historic Cabin Retreat From US $473
         

10.0 (56 Reviews)
Cabin
Rustic Luxury Near Charlottesville/Montpelier/Wineries/A Historic Cabin Retreat
  • Air Conditioner
  • Parking
  • Pet Friendly

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Rural and Spacious Virginia Home on about 2 Acres! From US $307
         

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9.7 (4 Reviews)
House
Rural and Spacious Virginia Home on about 2 Acres!
  • Parking
  • View
  • Accessibility

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Greenock Manor From US $276
         

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9.0 (45 Reviews)
House
Greenock Manor
  • Parking
  • Designated Smoking Area
  • TV

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“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations. From US $351
         

10.0 (34 Reviews)
House
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
  • Air Conditioner
  • Parking
  • TV

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Mayhurst Estate From US $313
         

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9.5 (30 Reviews)
Bed & Breakfast
Mayhurst Estate
  • Air Conditioner
  • Parking
  • Pet Friendly

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Inn at Willow Grove From US $431
         

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10.0 (61 Reviews)
Hotel
Inn at Willow Grove
  • Air Conditioner
  • Parking
  • Pool

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Luxury Stay on Flower Farm by Wineries Near Charlottesville-Pet-Friendly From US $393
         

10.0 (28 Reviews)
House
Luxury Stay on Flower Farm by Wineries Near Charlottesville-Pet-Friendly
  • Air Conditioner
  • Parking
  • Pet Friendly

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2 BR retreat in the heart of historic Gordonsville -Walkable to many attractions From US $230
         

10.0 (26 Reviews)
House
2 BR retreat in the heart of historic Gordonsville -Walkable to many attractions
  • Air Conditioner
  • Parking
  • TV

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Rural and Spacious Virginia Home on ~ 2 Acres! From US $259
         

10.0 (14 Reviews)
House
Rural and Spacious Virginia Home on ~ 2 Acres!
  • Air Conditioner
  • Parking
  • TV

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The Biltmore Suite in historic Holladay House From US $382
         

10.0 (5 Reviews)
House
The Biltmore Suite in historic Holladay House
  • Air Conditioner
  • Parking
  • TV

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350 Acre Estate just a mile from James Madison's Montpelier. From US $1,010
         

10.0 (4 Reviews)
House
350 Acre Estate just a mile from James Madison's Montpelier.
  • Air Conditioner
  • Parking
  • TV

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The Edgcote Room in Historic Holladay House From US $352
         

10.0 (4 Reviews)
House
The Edgcote Room in Historic Holladay House
  • Air Conditioner
  • Parking
  • TV

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The Blenheim Suite in historic Holladay House From US $350
         

10.0 (4 Reviews)
Apartment
The Blenheim Suite in historic Holladay House
  • Air Conditioner
  • Parking
  • TV

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Beautifully renovated 1780 historic estate and horse farm From US $465
         

10.0 (1 Review)
House
Beautifully renovated 1780 historic estate and horse farm
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Fenton Room in historic Holladay House From US $285
         

10.0 (1 Review)
House
The Fenton Room in historic Holladay House
  • Air Conditioner
  • Parking
  • TV

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Elegant Cottage on 600 Acre Horse & Livestock Farm From US $291
         

9.8 (149 Reviews)
Cottage
Elegant Cottage on 600 Acre Horse & Livestock Farm
  • Air Conditioner
  • Parking
  • Pet Friendly

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Servants' Cottage on 600 Acre Working Horse/Cattle Estate From US $199
         

9.8 (137 Reviews)
Cottage
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
  • Air Conditioner
  • Parking
  • Pet Friendly

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'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City. From US $309
         

9.8 (87 Reviews)
Cottage
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Newly renovated entire guest suite in Orange County. From US $177
         

9.8 (44 Reviews)
House
Newly renovated entire guest suite in Orange County.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Historic Manor House with Saltwater pool and Mountain Views From US $908
         

9.8 (8 Reviews)
House
Historic Manor House with Saltwater pool and Mountain Views
  • Air Conditioner
  • Parking
  • Pool

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Charming 3-Bed Cottage on Main Street in Historic Gordonsville From US $275
         

9.8 (8 Reviews)
House
Charming 3-Bed Cottage on Main Street in Historic Gordonsville
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Sailings makes it easy to compare the best listings on Sailings homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sailings homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in James Madison's Montpelier.

Weather in James Madison's Montpelier

View the weather forecast for James Madison's Montpelier before booking your James Madison's Montpelier Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around James Madison's Montpelier, VA

Sailings offers a large selection of top attractions around James Madison's Montpelier. Research things to do on your vacation before you visit James Madison's Montpelier.


University of Virginia Monticello Downtown Mall John Paul Jones Arena Lake Anna University of Virginia Hospital Trump Winery The Jefferson Theater Barboursville Vineyards Paramount Theater Charlottesville Pavilion Swift Run Gap Entrance SheNonedoah Old Rag Mountain Skyland Lake Anna State Park Scott Stadium Chancellorsville Battlefield Montpelier The Loft Fredericksburg and Spotsylvania National Military Park

James Madison's Montpelier Vacation Rental Frequently Asked Questions

How many vacation rentals are available in James Madison's Montpelier?

Currently, the total number of properties listed in 2026 is over 68 in the James Madison's Montpelier area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in James Madison's Montpelier.