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Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Woodstock vacation rentals

Outdoor dining

Firefly cottage with Ocean view

Firefly cottage with Ocean view
Cave District
10.0 out of 10, Exceptional, (27 reviews)
"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
Jul 29 - Jul 30
Total with taxes and fees
Firefly cottage with Ocean view
Property grounds

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

The Artist cabin is a mountain cabin overlooking the sea and coastline
Cave
10.0 out of 10, Exceptional, (1 review)
"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
Jul 18 - Jul 19
Total with taxes and fees
The Artist cabin is a mountain cabin overlooking the sea and coastline
Smart TV

Perfect 2-bedroom house in Bethany Dist, St. Elizabeth for your hide-away stay.

Perfect 2-bedroom house in Bethany Dist, St. Elizabeth for your hide-away stay.
Watchwell P.O.
10.0 out of 10, Exceptional, (1 review)
"Everything about this property was perfect! It’s super clean, located in a quiet neighborhood, and the host was incredibly helpful and always easy to reach. Best place I’ve stayed at by far!"
United States
Chantaye K.
$131 nightly
The price is $131
Jul 27 - Jul 28
Total with taxes and fees
Perfect 2-bedroom house in Bethany Dist, St. Elizabeth for your hide-away stay.
1 bedroom, WiFi, bed sheets

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

Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Cave
9.0 out of 10, Wonderful, (2 reviews)
"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
Jul 20 - Jul 21
Total with taxes and fees
Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Property grounds

Dragon fly Cottage

Dragon fly Cottage
Cave
10.0 out of 10, Exceptional, (7 reviews)
"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
$99 nightly
The price is $99
Aug 14 - Aug 15
Total with taxes and fees
Dragon fly Cottage
Property grounds

Muris Light Sanctuary

Muris Light Sanctuary
Savanalamar
10.0 out of 10, Exceptional, (1 review)
"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
Jul 18 - Jul 19
Total with taxes and fees
Muris Light Sanctuary
Fridge, microwave, oven, stovetop

Luxury ocean view villa

Luxury ocean view villa
Westmoreland
7.6 out of 10, Good, (4 reviews)
"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.
$202 nightly
The price is $202
Jul 18 - Jul 19
Total with taxes and fees
Luxury ocean view villa
Exterior

Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!

Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!
Savanna la Mar
$140 nightly
The price is $140
Jul 18 - Jul 19
Total with taxes and fees
Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!
Pool

White Sky Beach Villas

White Sky Beach Villas
New Hope
$1,086 nightly
The price is $1,086
Jul 21 - Jul 22
Total with taxes and fees
White Sky Beach Villas
Exterior

Relaxing retreat at Paradise Palms Estate. Minutes away from Appleton Estate.

Relaxing retreat at Paradise Palms Estate. Minutes away from Appleton Estate.
Newmarket
$457 nightly
The price is $457
Aug 1 - Aug 2
Total with taxes and fees
Relaxing retreat at Paradise Palms Estate. Minutes away from Appleton Estate.
Terrace/patio

Unvergessliche Villa, eine atemberaubende Flucht direkt am Strand by Interhome

Unvergessliche Villa, eine atemberaubende Flucht direkt am Strand by Interhome
Treasure Beach
$1,147 nightly
The price is $1,147
Jul 19 - Jul 20
Total with taxes and fees
Unvergessliche Villa, eine atemberaubende Flucht direkt am Strand by Interhome
Interior

Calabura Villa - White House Modern Luxury Villa

Calabura Villa - White House Modern Luxury Villa
Whitehouse
$1,371 nightly
The price is $1,491
Jul 31 - Aug 1
Total with taxes and fees
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

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

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

8/10 Good
"Apart from occasional internet outages and slow internet speeds, everything was ok.If you need to spend some time without a chef or helper, my advice is to bring enough food and snacks with you, as there are no supermarkets nearby. You'll need to drive out to find one."
Christine Z. 2-night trip
Posted 2 months ago
Ocean Paradise: 6BR, 5BA, Pool, OceanFront Villa with a Private Beach

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?

An Oceanfront Getaway - Wheelchair Accessible with Private Pool.: This vacation home rental near Woodstock is located on the waterfront and has an outdoor pool, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Bluefields Bay are a couple of picturesque spots to get outside and enjoy nature. Bluefields Beach and Appleton Estate 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.