Holiday Rentals in Woodstock

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Our top choices for Woodstock holiday rentals

Holiday Home in Cave District

Firefly cottage with Ocean view
10.0 out of 10, Exceptional, (27)
"I would recommend this cabin resort to anyone. Geneva was wonderful host, along with her beautiful family"
United States
Rick B.
The price is €80
includes taxes & fees
25 Jan - 26 Jan 2026
Firefly cottage with Ocean view
The price is €121
includes taxes & fees
23 Jan - 24 Jan 2026
Perfect 2-bedroom house in charming, Hounslow Dist, St. Elizabeth for your stay.
10.0 out of 10, Exceptional, (1)
"We had an amazing stay in the mountains of Jamaica! The food was excellent, and we loved watching the sunset every evening. Terry was wonderful company — he even picked us up in Negril to bring us to the beautiful cabins in the woods. A truly magnificent stay!"
United States
Ana G.
The price is €63
includes taxes & fees
31 Dec - 1 Jan 2026
The Artist cabin is a mountain cabin overlooking the sea and coastline
9.0 out of 10, Wonderful, (2)
"Absolutely gorgeous property and views, bird sounds, fantastic food prepared by the friendly hosts. Simple living with wi-fi if needed."
United States
David G.
The price is €72
includes taxes & fees
31 Dec - 1 Jan 2026
Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Holiday Home in Whitehouse

Mini Cozy Lodging
3.0 star property
The price is €116
includes taxes & fees
1 Jan - 2 Jan 2026
Mini Cozy Lodging

Holiday Home in Cave

Dragon fly Cottage
10.0 out of 10, Exceptional, (7)
"We had a lot of fun relaxing here. Geneva made excellent breakfast and suppers and we spent the majority of our time relaxing on the deck/hammock reading and hiking around the property and the town of Kentucky. If you want an escape from the tourism scene, this is a nice place to go! "
Canada
Kaili
The price is €75
includes taxes & fees
31 Dec - 1 Jan 2026
Dragon fly Cottage
The price is €89
includes taxes & fees
31 Dec - 1 Jan 2026
One Bedroom Apartment minutes from Ys Falls, Safari and Zoo: Royale Flush Suites
The price is €183
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy 2-bedroom 2.5 bathroom villa in Black River with beach in the backyard

Villa in Westmoreland

Luxury ocean view villa
7.6 out of 10, Good, (4)
"Chef Donna if we could take her home with us we would! Anything that you need Marvette, Marca or Sheldon will get for you! We will definitely be back with a group again! I promise you , you won’t be disappointed!"
United States
Danete G.
The price is €199
includes taxes & fees
26 Jan - 27 Jan 2026
Luxury ocean view villa
The price is €196
includes taxes & fees
31 Dec - 1 Jan 2026
Mellow Breeze where you can relax or play
The price is €123
includes taxes & fees
31 Dec - 1 Jan 2026
Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!

Holiday Home in Savanalamar

Muris Light Sanctuary
10.0 out of 10, Exceptional, (1)
"Host was attentive and super nice to deal with. Great stay. No air conditioning but was pleaaant regardless. "
Canada
Leeann D.
The price is €117
includes taxes & fees
31 Dec - 1 Jan 2026
Muris Light Sanctuary
The price is €357
includes taxes & fees
31 Dec - 1 Jan 2026
5 minutes to Appleton Estate & 20 minutes to Maroon town. Griffiths Guest House.
The price is €982
includes taxes & fees
31 Dec - 1 Jan 2026
Waterfront Villa with Pool on Jamaica's South Coast
The price is €570
includes taxes & fees
31 Dec - 1 Jan 2026
Relaxing retreat at Paradise Palms Estate. Minutes away from Appleton Estate.
The price is €1,300
includes taxes & fees
1 Jan - 2 Jan 2026
Calabura Villa - White House Modern Luxury Villa
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 Woodstock Hotel Reviews

Find out more about Woodstock

Everything you need to know about Woodstock holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodstock holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Woodstock holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodstock. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodstock holiday rentals we have selected for you start as low as €63 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Woodstock rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodstock holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodstock. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Woodstock?

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

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

Lovely 2-bedroom Townhouse: This holiday home rental outside of Woodstock has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Woodstock?

With 64 Expedia holiday rentals, you're guaranteed to find just the right place for your Woodstock stay.

What can I see and do in Woodstock?

While you're exploring the area, YS Falls and Bubbling Spring Mineral Bath are a couple of picturesque spots to get outside and enjoy nature. Appleton Estate and Floyd's Pelican Bar are a couple of places you'll find in the wider area.

What are holiday rentals like in Woodstock?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodstock. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family getaway.