Vacation rentals in Somerset

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Top-rated holiday rentals in Somerset

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guesthouse in Orange
Taj Garage Guesthouse
Newly constructed (2021) above garage guesthouse with private, self check-in entrance, off-street parking, located among historic homes just 4 blocks to restaurants, shops, park and art galleries in downtown Orange. Guesthouse includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Handcrafted heart pine furniture. Level 2 EV Charger. Kitchen includes refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites.
16 – 23 June
5.0 out of 5 average rating, 174 reviews
Guest favourite
Apartment in Madison
The Studio at Dark Run Retreat
Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*
26 Mar – 2 Apr
4.9 out of 5 average rating, 228 reviews
Guest favourite
Apartment in Somerset
Newly Renovated•Private Farm Apartment near Cville
Come experience a relaxing getaway on our family’s dairy farm! Set in beautiful Orange County, We are close enough to Charlottesville (25 min) to fulfill all your shopping and eating needs, but have the privacy, calm and tranquility of the country, with beautiful majestic mountain views! This is a wonderful location for exploring all of wine country, unwinding from the hustle of busy life, and then taking in the sunset in this quiet country setting with rolling hills as your backdrop!
1 – 8 Sept
4.99 out of 5 average rating, 140 reviews

Popular amenities for Somerset holiday rentals

Other great holiday rentals in Somerset

Guest favourite
Cabin in Ruckersville
Mountain View’s cabin!
2 – 9 May
4.93 out of 5 average rating, 358 reviews
Guest favourite
Tiny home in Gordonsville
Glamping Cabin, Gorgeous Views, Sunsets! 1
11 – 18 Oct
4.94 out of 5 average rating, 115 reviews
Guest favourite
Guesthouse in Reva
Adorable cottage with partial blue ridge views
30 Dec – 6 Jan
4.97 out of 5 average rating, 138 reviews
Guest favourite
Cabin in Somerset
Log Cabin Near Charlottesville & Wineries/Sauna
24 June – 1 July
5.0 out of 5 average rating, 14 reviews
Guest favourite
Guesthouse in Orange
The Tower at Featherhill
3 – 8 Dec
4.96 out of 5 average rating, 82 reviews
Guest favourite
Home in Orange
The Rapidan Road Retreat
10 – 17 Jan
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Gordonsville
Clifton House- a beautifully renovated 1780 home
4 – 11 June
5.0 out of 5 average rating, 65 reviews
Guest favourite
Guest suite in Ruckersville
Summerfields Place
21 – 28 Jan
4.97 out of 5 average rating, 65 reviews
Guest favourite
Home in Orange
Porterfield Place- A Unique & Cozy Stay
25 Dec – 1 Jan
4.85 out of 5 average rating, 55 reviews
Guest favourite
Cottage in Gordonsville
Restored Historic Stone Greenhouse
5 – 12 Nov
4.97 out of 5 average rating, 34 reviews
Guest favourite
Cottage in Gordonsville
Shade Tree Cottage: Pet Friendly + Fire Pit
6 – 13 May
5.0 out of 5 average rating, 48 reviews
Guest favourite
Home in Orange
One of Central Virginia's Finest
29 June – 6 July
4.97 out of 5 average rating, 31 reviews

Destinations to explore

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  2. United States
  3. Virginia
  4. Orange County
  5. Somerset