Title: Highland County Vacation Packages 2026 from $473 | Expedia.com [Highland County Hotels](https://expedia.com/Destinations-In-Highland-County.d553248635976430568.Hotel-Destinations)[Vacation Rentals in Highland County](https://expedia.com/Destinations-In-Highland-County.d553248635976430568.Vacation-Rental-Destinations)[Highland County Flights](https://expedia.com/Destinations-In-Highland-County.d553248635976430568.Flight-Destinations)[Car Rentals in Highland County](https://expedia.com/Destinations-In-Highland-County.d553248635976430568.Car-Rental-Destinations) ![](https://images.trvl-media.com/place/553248635976430568/847a9f9b-6586-4c89-9916-af4de1709ae9.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Highland County Vacations & Trips from $473 ## Book a Hotel + Flight or Car together to unlock savings ### Your Highland County Vacation Leave all the planning to us with a Highland County vacation package. With everything organized before you leave home, the only thing you'll need to do is relax and experience this destination's many wonders. Get your trip to Highland County off to an unforgettable start by making [Monterey](https://www.expedia.com/Monterey.d184102.Destination-Travel-Guides) your first stop. This is a popular city with visitors from all over. From the instant you book your Highland County vacation to the second you come back home, Expedia has your back every step of the way. ## Top destinations in Highland County ![Rural Virginia Farm country in Autumn in the valleys and hills of the Appalachian Mountains](https://images.trvl-media.com/place/184102/1f9dfe79-6040-40f4-966d-fd0fd1de7bfe.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Monterey [](https://expedia.com/Monterey.d184102.Destination-Travel-Guides) ## The Latest Highland County Vacation Packages Price found within the past 48 hours. Click for updated prices. ![Extended Stay America Premier Suites - Harrisonburg](https://images.trvl-media.com/lodging/107000000/106240000/106238300/106238285/3a11a073_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Extended Stay America Premier Suites - Harrisonburg $473 per person May 22 - May 29 found 21 hours ago Roundtrip flight included Detroit (DTT) to Weyers Cave (SHD) 8.8/10 Excellent! (910 reviews) The staff was very friendly and check in was very fast with no hassle... +++++! Rooms were spacious and clean ...+++++.. Reviewed on Mar 31, 2026 ![Doubletree by Hilton Harrisonburg](https://images.trvl-media.com/lodging/1000000/20000/17700/17690/69258cb6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Doubletree by Hilton Harrisonburg $999 per person May 13 - May 15 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Weyers Cave (SHD) 8.2/10 Very Good! (1,003 reviews) The pool was very nice and easily the best part. People were kind. Had issues with the room, breakfast, people there were apologetic but that was it, didn't offer any resolution. So it was ok Reviewed on Mar 29, 2026 ![Hyatt Studios Harrisonburg](https://images.trvl-media.com/lodging/123000000/122730000/122728100/122728090/43b5f69a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Studios Harrisonburg $898 per person May 13 - May 15 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Weyers Cave (SHD) No reviews ![Mountainside Villas at Massanutten by Tripforth](https://images.trvl-media.com/lodging/44000000/43590000/43583000/43582998/0fc3b312_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mountainside Villas at Massanutten by Tripforth $918 per person May 13 - May 15 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Weyers Cave (SHD) 9/10 Wonderful! (369 reviews) The in-unit sauna is lovely, and the unit had all that we needed for a short stay. We've stayed in the Mountainside Villas 3 times, and always enjoy the amenities, especially the proximity to the Rec & Fitness Center. The villa could have used a deep clean, and hot water had a hard time getting to the upstairs shower, but otherwise a great time for the whole family! Reviewed on Mar 31, 2026 ![Massanuttens Shenandoah Villas by Tripforth](https://images.trvl-media.com/lodging/44000000/43550000/43548500/43548428/ac22e2e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Massanuttens Shenandoah Villas by Tripforth $869 per person May 13 - May 15 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Weyers Cave (SHD) 7.6/10 Good! (153 reviews) The resort is very family friendly! Many parks, pools, so many activities! We had deer outside of our place daily it was great! The views were amazing. The only bad review is the cleanliness. I mean the walls were dirty, many cobwebs/dust. The floor needed a vacuum when we got there. A dead roach welcomed me when we walked into one of the rooms. They have a checkout checklist of things you need to do. I completely understand cleaning up after selves but it would be nice if the resort would make sure these villas are clean! Reviewed on Mar 11, 2026 ## Find the Best Highland County Vacation Packages ## Highland County Essential Information | Language | English | | --------------- | ----------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Ronald Reagan Washington National Airport (DCA) | ## Highland County Hotel Deals ![Simple. Rustic. Luxury.](https://images.trvl-media.com/lodging/34000000/33710000/33707900/33707889/4938f099_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Simple. Rustic. Luxury. Monterey VA [Get rates](https://expedia.com/Hotel-Search?startDate=4%2F16%2F2026&endDate=4%2F17%2F2026&selected=33707889&PinnedHotelID=33707889&HadPinnedHotel=true®ionId=553248635976430568) [](https://expedia.com/Hotel-Search?startDate=4%2F16%2F2026&endDate=4%2F17%2F2026&selected=33707889&PinnedHotelID=33707889&HadPinnedHotel=true®ionId=553248635976430568) ![Monterey Inn](https://images.trvl-media.com/lodging/94000000/93260000/93250200/93250178/560db505_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Monterey Inn 32 W Main St Monterey VA $209 nightly $231 total Apr 5 - Apr 6 Total with taxes and fees 9.4/10 Exceptional! (43 reviews) The room was nice and clean. there were flies comming in upstairs but that is truely typical of a house of this age. The owner had asked us to pay a couple of taxes that were not listed in the price (not sure it is ethical/legal/moral) - they close by 9 or you have to pay a $50 late fee A fee - no ... Reviewed on Feb 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=93250178&PinnedHotelID=93250178&HadPinnedHotel=true®ionId=553248635976430568) ![Games Galore! Riverfront Group Retreat in McDowell](https://images.trvl-media.com/lodging/124000000/123360000/123352900/123352818/5c2e87b6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Games Galore! Riverfront Group Retreat in McDowell McDowell VA 10/10 Exceptional! (5 reviews) Amazing! Our group had the most incredible time at this stunning riverfront retreat! From the moment we arrived, we were blown away by how spacious, welcoming, and beautifully appointed the home is. With 10 bedrooms and plenty of room for everyone, it was perfect for our multi-family getaway — and the views ... Reviewed on Feb 19, 2026 [Get rates](https://expedia.com/Hotel-Search?startDate=4%2F16%2F2026&endDate=4%2F17%2F2026&selected=123352818&PinnedHotelID=123352818&HadPinnedHotel=true®ionId=553248635976430568) [](https://expedia.com/Hotel-Search?startDate=4%2F16%2F2026&endDate=4%2F17%2F2026&selected=123352818&PinnedHotelID=123352818&HadPinnedHotel=true®ionId=553248635976430568) [See all 1,364 properties in Highland County](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F3%2F2026&endDate=4%2F4%2F2026®ionId=553248635976430568) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) Explore a world of travel with Expedia ## Other vacations you might like - Top cities in Highland County - Vacations and getaways similar to Highland County - Best vacation destinations by month - [Monterey Vacations ](https://expedia.com/Monterey.d184102.Destination-Travel-Guides) - [Doe Hill Vacations ](https://expedia.com/Doe-Hill.d553248635975978080.Destination-Travel-Guides) - [North Carolina Vacations ](https://expedia.com/North-Carolina.d235.Destination-Travel-Guides) - [Tennessee Vacations ](https://expedia.com/Tennessee.d244.Destination-Travel-Guides) - [Maryland Vacations ](https://expedia.com/Maryland.d222.Destination-Travel-Guides) - [Kentucky Vacations ](https://expedia.com/Kentucky.d219.Destination-Travel-Guides) - [West Virginia Vacations ](https://expedia.com/West-Virginia.d250.Destination-Travel-Guides) - [District of Columbia Vacations ](https://expedia.com/District-Of-Columbia.d210.Destination-Travel-Guides) - [January Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-january) - [February Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-february) - [March Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-march) - [April Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-april) - [May Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-may) - [June Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-june) - [July Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-july) - [August Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-august) - [September Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-september) - [October Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-october) - [November Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-november) - [December Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-december) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.