Woodstock Vacation Rentals

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Nov 21 - Nov 22
Tomorrow
Nov 22 - Nov 23
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Woodstock

Pool
Oceanview lux Villa + Infinity pool, Chef & Butler

Villa in Southsea Park Westbay

10.0 out of 10, Exceptional, (2)
"My clients were happy with their stay and the villa manager was great to work with! The extra touches she added to the 60th birthday made everything even more special. The food was delicious as well and they stated the grounds people were great and accommodating as well! It’s a great location for those that have been to Jamaica several times and want to explore other areas. I would definitely stay here again!"
United States
Ronique M.
$3,047 nightly
The price is $3,047
Dec 2 - Dec 3
Total with taxes and fees
Oceanview lux Villa + Infinity pool, Chef & Butler
Property grounds
The Artist cabin is a mountain cabin overlooking the sea and coastline

Vacation Home in Cave

2.0 star property
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.
$70 nightly
The price is $70
Nov 23 - Nov 24
Total with taxes and fees
The Artist cabin is a mountain cabin overlooking the sea and coastline
Property grounds
Dragon fly Cottage

Vacation Home in 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
$83 nightly
The price is $83
Nov 23 - Nov 24
Total with taxes and fees
Dragon fly Cottage
Outdoor dining
Firefly cottage with Ocean view

Vacation Home in Cave District

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.
$79 nightly
The price is $79
Nov 23 - Nov 24
Total with taxes and fees
Firefly cottage with Ocean view
Exterior
Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Vacation Home in Cave

2.0 star property
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.
$80 nightly
The price is $80
Nov 24 - Nov 25
Total with taxes and fees
Kimoya's cottage is a mountain cottage overlooking the sea and coastline
House, 2 Bedrooms, Non Smoking, Kitchen | Private kitchen
Mini Cozy Lodging

Vacation Home in Whitehouse

3.0 star property
$118 nightly
The price is $137
Nov 23 - Nov 24
Total with taxes and fees
Mini Cozy Lodging
1 bedroom, free WiFi, bed sheets
One Bedroom Apartment minutes from Ys Falls, Safari and Zoo: Royale Flush Suites

Apartment in Middle Quarters

$100 nightly
The price is $100
Nov 23 - Nov 24
Total with taxes and fees
One Bedroom Apartment minutes from Ys Falls, Safari and Zoo: Royale Flush Suites
Pool
Calabura Villa - White House Modern Luxury Villa

Vacation Home in Whitehouse

$1,366 nightly
The price is $1,486
Nov 24 - Nov 25
Total with taxes and fees
Calabura Villa - White House Modern Luxury Villa
On the beach
Cozy 2-bedroom 2.5 bathroom villa in Black River with beach in the backyard

Villa in St. Elizabeth Parish

$206 nightly
The price is $209
Nov 24 - Nov 25
Total with taxes and fees
Cozy 2-bedroom 2.5 bathroom villa in Black River with beach in the backyard
Property grounds
Mellow Breeze where you can relax or play

Vacation Home in Greenwood

$225 nightly
The price is $225
Nov 23 - Nov 24
Total with taxes and fees
Mellow Breeze where you can relax or play
Property grounds
Muris Light Sanctuary

Vacation Home in Savanalamar

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.
$133 nightly
The price is $133
Nov 23 - Nov 24
Total with taxes and fees
Muris Light Sanctuary
Outdoor pool
Waterfront Villa with Pool on Jamaica's South Coast

Vacation Home in White House

$1,028 nightly
The price is $1,156
Nov 23 - Nov 24
Total with taxes and fees
Waterfront Villa with Pool on Jamaica's South Coast
Exterior
Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!

Apartment in Savanna la Mar

$140 nightly
The price is $140
Nov 23 - Nov 24
Total with taxes and fees
Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!
Pool
Luxury ocean view villa

Villa in Westmoreland

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.
$205 nightly
The price is $205
Dec 7 - Dec 8
Total with taxes and fees
Luxury ocean view villa
Property grounds
5 minutes to Appleton Estate & 20 minutes to Maroon town. Griffiths Guest House.

Vacation Home in St. Elizabeth Parish

$412 nightly
The price is $412
Nov 23 - Nov 24
Total with taxes and fees
5 minutes to Appleton Estate & 20 minutes to Maroon town. Griffiths Guest House.
Property grounds
Relaxing retreat at Paradise Palms Estate. Minutes away from Appleton Estate.

Vacation Home in Newmarket

$654 nightly
The price is $654
Dec 5 - Dec 6
Total with taxes and fees
Relaxing retreat at Paradise Palms Estate. Minutes away from Appleton Estate.
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

Oceanview lux Villa + Infinity pool, Chef & Butler

Oceanview lux Villa + Infinity pool, Chef & Butler

10/10 Excellent
"My clients were happy with their stay and the villa manager was great to work with! The extra touches she added to the 60th birthday made everything even more special. The food was delicious as well and they stated the grounds people were great and accommodating as well! It’s a great location for those that have been to Jamaica several times and want to explore other areas. I would definitely stay here again!"
Ronique M. 3-night trip
Posted 2 months ago
Oceanview lux Villa + Infinity pool, Chef & Butler

Find out more about Woodstock

Everything you need to know about Woodstock vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodstock vacation 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 low season months. For more hustle and bustle, you may prefer to visit Woodstock in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $70 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock vacation 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 vacation.

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 vacation rentals in Woodstock?

Yes, we offer vacation rentals near well known attractions in Woodstock, or you can go with a secluded option if you're looking for relaxation.

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

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

How many vacation rentals are there in Woodstock?

With 64 Expedia vacation rentals, you're sure 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 larger area.

What are vacation rentals like in Woodstock?

Vacation rentals are private properties you can reserve for a couple days or more in Woodstock. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a small group gathering.