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Woodstock Vacation Rentals

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Woodstock vacation rentals

Property grounds

1. 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
Sep 11 - Sep 12
Total with taxes and fees
The Artist cabin is a mountain cabin overlooking the sea and coastline
Outdoor dining

2. 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
Sep 15 - Sep 16
Total with taxes and fees
Firefly cottage with Ocean view
Exterior

3. 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
Sep 12 - Sep 13
Total with taxes and fees
Relaxing retreat at Paradise Palms Estate. Minutes away from Appleton Estate.
Room

4. 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
Sep 14 - Sep 15
Total with taxes and fees
Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Property grounds

5. 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
Sep 30 - Oct 1
Total with taxes and fees
Dragon fly Cottage
Private kitchen

6. 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.
$201 nightly
The price is $201
Sep 14 - Sep 15
Total with taxes and fees
Luxury ocean view villa
Property grounds

7. 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
Sep 11 - Sep 12
Total with taxes and fees
Muris Light Sanctuary
Room

8. Modern 1BR Apartment with AC, WiFi & Free Parking in Santa Cruz

Modern 1BR Apartment with AC, WiFi & Free Parking in Santa Cruz
Santa cruz
$97 nightly
The price is $97
Sep 11 - Sep 12
Total with taxes and fees
Modern 1BR Apartment with AC, WiFi & Free Parking in Santa Cruz
Interior

9. Calabura Villa - White House Modern Luxury Villa

Calabura Villa - White House Modern Luxury Villa
Whitehouse
$1,371 nightly
The price is $1,491
Sep 13 - Sep 14
Total with taxes and fees
Calabura Villa - White House Modern Luxury Villa
Room

10. Cozy 3-bedroom house in serene Santa Cruz with AC

Cozy 3-bedroom house in serene Santa Cruz with AC
Santa Cruz
$165 nightly
The price is $165
Sep 11 - Sep 12
Total with taxes and fees
Cozy 3-bedroom house in serene Santa Cruz with AC
Living area

11. 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.
$158 nightly
The price is $158
Sep 21 - Sep 22
Total with taxes and fees
Perfect 2-bedroom house in Bethany Dist, St. Elizabeth for your hide-away stay.
Living area

12. Beautiful 2-bedroom house with AC in peaceful Savanna la mar

Beautiful 2-bedroom house with AC in peaceful Savanna la mar
Savanna la mar
10.0 out of 10, Exceptional, (1 review)
"From the moment I arrived, the property felt very secure, which immediately gave me peace of mind. The space itself was warm, cozy, and inviting it really felt like a home away from home rather than just a place to sleep.The amenities were exactly as advertised and on point. Everything I needed for a comfortable stay was readily available, and the overall setup made it easy to settle in and relax.One of the standout parts of the stay was the communication with the host, Latoya She was excellent,...
United States
Chris R.
$228 nightly
The price is $228
Sep 12 - Sep 13
Total with taxes and fees
Beautiful 2-bedroom house with AC in peaceful Savanna la mar
Exterior

13. 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
Sep 11 - Sep 12
Total with taxes and fees
Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!
Terrace/patio

14. Unvergessliche Villa, eine atemberaubende Flucht direkt am Strand by Interhome

Unvergessliche Villa, eine atemberaubende Flucht direkt am Strand by Interhome
Treasure Beach
$1,165 nightly
The price is $1,165
Sep 21 - Sep 22
Total with taxes and fees
Unvergessliche Villa, eine atemberaubende Flucht direkt am Strand by Interhome
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

Santosha - 10BR Luxury Villa, Fully Staffed

Santosha - 10BR Luxury Villa, Fully Staffed

10/10 Excellent
"Amazing villa, wonderful staff, and an unforgettable experience!We had an amazing stay and would absolutely consider returning. The villa was beautiful, the food was incredible, and the staff went above and beyond to make our experience special. Everyone was welcoming, attentive, and professional, and communication before and throughout our stay was generally very responsive.The only concern we experienced involved the food pricing. The final food cost was approximately double the amount we had anticipated based on the amount originally communicated to us. The food itself was excellent and enjoyed by everyone, but we would recommend that future guests request a detailed, written breakdown of the food costs beforehand so expectations are completely clear.That concern aside, our group genuinely loved the villa and the staff, and we created memories that we will never forget. The property and service absolutely deserve five stars, and we would be happy to stay here again."
PRESTON S. 4-night trip
Posted 12 days ago
Santosha - 10BR Luxury Villa, Fully Staffed

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?

Firefly cottage with Ocean view: This vacation home rental near Woodstock is located in the mountains and has a balcony, a garden, and WiFi to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. Make the most of the selection of games in this rental home to help you unwind.

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.