Woodstock Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Woodstock holiday rentals

Lovely 2-bedroom Townhouse

Savanna la Mar
10.0 out of 10, Exceptional, (2)
"Enjoyed the stay."
United States
Henry
Lovely 2-bedroom Townhouse

Villa Serene Jewel of Black River 4 bedroom 5bathrooms

Black River
9.6 out of 10, Exceptional, (11)
"The pictures do not give this Villa justice, it is beautiful! We had an amazing time there! We were looking for rest and relaxation and that is exactly what we got!! Shamoir the cook was incredible! Sheryl was quick to respond to any questions we had! We will definitely go back!"
United States
diana s.
Villa Serene Jewel of Black River 4 bedroom 5bathrooms

Oceanfront Luxury Villa: Private Beach & Staff

Treasure Beach
9.6 out of 10, Exceptional, (34)
"The "Great Escape" is a lovely place for a vacation. Far off the beaten (touristic) path, quiet, peaceful, with a large Pool and a lovely seaside terrace. Shane is a great cook, we enjoyed those meals so much."
Germany
Markus B.
Oceanfront Luxury Villa: Private Beach & Staff

Award-winning villa with private beachfront and pool

Culloden White House
10.0 out of 10, Exceptional, (1)
"Just what the family needed. This will be an annual experience. "
United States
Andrew R.
Award-winning villa with private beachfront and pool

10BR Luxury Villa w/ Private Beach , Fully Staffed w/ Chef - STSHA

Sandy Ground
10.0 out of 10, Exceptional, (1)
"Perfect for our team of 18! Everyone enjoyed the food, the staff, the ambience. It was great to have our own privacy to bond as a team. Everything was immaculate! Minor problems- The internet connectivity was slow or didn't work, and the power tripped out 1-2 times per day, however, speedily restored by our butler."
United States
Anna L.
10BR Luxury Villa w/ Private Beach , Fully Staffed w/ Chef - STSHA

Deano's Cottages

3.0 star property
Black River
6.8 out of 10, (5)
"Very quiet, felt very safe "
United States
Derrick
Deano's Cottages

Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!

Savanna la Mar
The price is AU$214
includes taxes & fees
16 Dec - 17 Dec
Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!

2 Bedroom Beachfront Property in Westmoreland

White House
2 Bedroom Beachfront Property in Westmoreland

Fantastic, spacious villa with a large pool and sea views in a very safe area.

Westmoreland
8.8 out of 10, Excellent, (13)
"The rooms and pool are very good. Getting back down the steep and long drive during hours of darkness is difficult."
United Kingdom
David E.
Fantastic, spacious villa with a large pool and sea views in a very safe area.

Cozy 2-bedroom 2.5 bathroom villa in Black River with beach in the backyard

St. Elizabeth Parish
The price is AU$319
includes taxes & fees
10 Dec - 11 Dec
Cozy 2-bedroom 2.5 bathroom villa in Black River with beach in the backyard

Private beachfront paradise 2cottages & 2 rooms in Bluefield's Bay AC, Wi-Fi

2.0 star property
Bluefields
Private beachfront paradise 2cottages & 2 rooms in Bluefield's Bay AC, Wi-Fi

Ocean Paradise: 6BR, 5BA, Pool, OceanFront Villa with a Private Beach

Treasure Beach
6.0 out of 10, (1)
"Amazing site, lush vegetation, multiple places to relax and enjoy the scenery. Great pool, kayaks, etc. Two houses is also a plus. Beach relatively small but clean. Unfortunately the two villas show their age: old furniture but generally clean. Our main problem with this rental was that the kitchen was dirty. Dishes and utensils had food residus, many of the small appliances (toaster, coffee machine, etc were dirty and stained) and the kitchen was infested by ants. There is no garbage can in...
Canada
Gilles P.
Ocean Paradise: 6BR, 5BA, Pool, OceanFront Villa with a Private Beach

Kimoya's cottage is a mountain cottage overlooking the sea and coastline

2.0 star property
Cave
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 AU$123
includes taxes & fees
31 Dec - 1 Jan 2026
Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Aristo Oasis, come and unwind in paradise. Santa Cruz Jamaica. 5 mins to Town

St Elizabeth
10.0 out of 10, Exceptional, (1)
"Great neighborhood. Safe environment. Awesome host"
United States
Joan M.
Aristo Oasis, come and unwind in paradise. Santa Cruz Jamaica. 5 mins to Town

“Something Blue” Entire property in Westmoreland, Jamaica Cozy 3 bedroom home

Savanna la mar
“Something Blue” Entire property in Westmoreland, Jamaica Cozy 3 bedroom home

White Sky Beach Villas

New Hope
White Sky Beach Villas

Dragon fly Cottage

Cave
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 AU$152
includes taxes & fees
31 Dec - 1 Jan 2026
Dragon fly Cottage

The Artist cabin is a mountain cabin overlooking the sea and coastline

2.0 star property
Cave
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 AU$108
includes taxes & fees
31 Dec - 1 Jan 2026
The Artist cabin is a mountain cabin overlooking the sea and coastline

The Belair

3.5 star property
Bluefields
The Belair

Luxurious 3 beds, 2 bath with all amenities

Savanna la Mar
10.0 out of 10, Exceptional, (1)
"It was such a great experience staying at the home. Felt safe and enjoyed the amenities offered. We stayed as a group and everyone was satisfied with their stay. Will definitely be returning the next time we are in Sav La Mar. thanks for prompt response to our questions. Much appreciated."
Canada
Eustace
Luxurious 3 beds, 2 bath with all amenities
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.
Save an average of 15% on thousands of hotels when you're signed in

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, 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 favourite 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 depend 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 AU$108 per night. Entering your travel dates in the search wizard might find you 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 Parrotee Pond Mangroves 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.