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Top Holiday Rentals in Greenwood

Isolated cottage with good view close to many winery and Brewers.

9.0 out of 10, Wonderful, (22)
"It was great thank you"
The price is £197
includes taxes & fees
27 Aug - 28 Aug
Isolated cottage with good view close to many winery and Brewers.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (191)
"Quite and Accommodating.office staff was great "
The price is £91
includes taxes & fees
24 Aug - 25 Aug
Valley Extended Suites

Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area

10.0 out of 10, Exceptional, (14)
"We loved staying at this property. Easily accommodated our family and was such a pretty setting. Host was excellent in answering questions and providing information. Would definitely stay here in the future."
Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (86)
"This is a great place to stay. Close to town but out on a large very private farm. Highly recommend. "
1802 cottage once part of Monticello and owned by Thomas Jefferson

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (290)
"The condo has just the right amenities, nicely decorated, and yes, a million dollar view."
The price is £184
includes taxes & fees
21 Aug - 22 Aug
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Afton Mountain Vineyards

2.5 star property
The price is £291
includes taxes & fees
21 Aug - 22 Aug
Afton Mountain Vineyards

New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

9.6 out of 10, Exceptional, (131)
"This was such a beautiful, clean space. Every item had been thought of; there was even a closet with dog treats, flashlights, extra toothbrushes, etc! Parking and check in were a breeze. The host was incredibly responsive. Take the short walk to Fire and Frost for delicious pizza!"
The price is £189
includes taxes & fees
21 Aug - 22 Aug
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

9.8 out of 10, Exceptional, (50)
"This was our second stay in Wintergreen. First time at this property. The condo was beautifully decorated, had all the necessities and the view was breathtaking. "
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

Family Friendly Log Cabin Nestled in Blue Ridge Foothills

2.0 star property
9.8 out of 10, Exceptional, (9)
"Very well equipped and clean! The owner was super nice and responsive! Great stay!"
Family Friendly Log Cabin Nestled in Blue Ridge Foothills

Downtown Carriage House | 1 BR Loft close to the historic downtown mall

9.4 out of 10, Exceptional, (70)
"Second stay here and all good!! "
Downtown Carriage House | 1 BR Loft close to the historic downtown mall

New Cabin Right on The Rockfish River! Peacefull River Sounds, Stunning views!

10.0 out of 10, Exceptional, (45)
"Beautiful house, setting and walking path. "
New Cabin Right on The Rockfish River! Peacefull River Sounds, Stunning views!

Cozy Cabin with private HOT TUB!

10.0 out of 10, Exceptional, (25)
"Adult girls weekend visiting local wineries, Breweries, and, of course, Bold Rock Cidery. Great location. Beautiful mountain views on the way up to the cabin. The hot tub was perfect for evening relaxation. Plenty of room, and well-appointed kitchen. "
Cozy Cabin with private HOT TUB!

Wow! What A View!

9.4 out of 10, Exceptional, (15)
"Découverte de la corse pour la 1ère fois. Proche de tous, plage, équitation mer montagne, spécialités, petit port avec restau,rando, village et super point de vue."
Wow! What A View!

Bear Tracks Cottage: New Hot Tub + Fire Pit

10.0 out of 10, Exceptional, (20)
"Great for taking advantage of all Nelson County's attractions. "
The price is £326
includes taxes & fees
21 Aug - 22 Aug
Bear Tracks Cottage: New Hot Tub + Fire Pit

Aftonshire Cottage - Heart of Afton's Wine Region

10.0 out of 10, Exceptional, (4)
"Place was nice an quite and had a good view of the horses outback. The location was great and close to restaurants and wineries. "
Aftonshire Cottage - Heart of Afton's Wine Region

Numerous On-Site Trails: Earlysville Wooded Cabin

9.8 out of 10, Exceptional, (73)
"Great place to stay to visit Shenandoah national Park and surrounding area. Host was a great communicator and made sure we had everything we needed. Would definitely stay here again."
Numerous On-Site Trails: Earlysville Wooded Cabin

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

8.0 out of 10, Very good, (1)
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

The Firefly Springhouse

10.0 out of 10, Exceptional, (31)
"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."
The price is £88
includes taxes & fees
21 Aug - 22 Aug
The Firefly Springhouse

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

9.8 out of 10, Exceptional, (48)
"Great place, easy to find, and quick drive to the Wontergreen Resort!"
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

10.0 out of 10, Exceptional, (51)
"Great place to stay. "
The price is £193
includes taxes & fees
21 Aug - 22 Aug
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
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.
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Top Greenwood Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its wineries.

What are some of the best holiday rentals that Greenwood has to offer?

Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!: This holiday home rental outside of Greenwood is located in the city centre, and offers a patio, air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware.

How many holiday rentals will I find in Greenwood?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Greenwood stay.

What’s there to see and do in Greenwood?

Explore the area and family-friendly sights such as War Fields, or get out into nature at a spot like Shenandoah National Park. In the wider area, you’ll find Pollak Vineyards and King Family Vineyards.

What’s a holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips.