Woodstock Holiday Rentals from €64: Search Short-Term Rentals

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

“Something Blue”Entire property in Westmoreland, Jamaica Cozy 3 bedroom home : This highly rated holiday home rental in Woodstock offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Some other top choices in Woodstock are The Artist cabin is a mountain cabin overlooking the sea and coastline and Firefly cottage with Ocean view .

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Holiday Rentals in Woodstock

Relax by the pool surrounded by lush greenery and a tranquil waterfall.

"As a woman who just buried her cousin & father within 1 week of arriving in JA, I was really looking forward to this trip as a means to clear my mind from everything that was going. We rented Villa Serene for the week so that my step-children & mother-in-law could all come to one location & spend some personal time together, especially since it was the first time I would be meeting them face to face. Villa Serene "could" be 5-star property if it were brought up to code (proper...

Relax on the patio with unobstructed ocean views and comfortable lounge chairs.

"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."

Relax by the pool surrounded by a serene beach scene mural and lush greenery.

"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!"

includes taxes & fees

25 Jul - 26 Jul

Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

"An absolute escape from reality. Property was great it was a hidden gem views where amazing Shane the property manager is excellent use him he is very knowledgeable of the area. And is awesome chef cooked breakfast everyday it was excellent “tip him well” only issue was beach and road leading too property Gve it strong 8/10 SHANE is why it’s so high "

Stroll along the beach path lined with lush greenery and palm trees, leading to a scenic ocean view.

"We loved the stay we made lots of new memories. We will be going back and stay here. It’s private and it’s beautiful. The home is very modern with all the amenities anyone needs for a fun filled vacation. The entire staff were amazing the food was spectacular. We stayed at resorts in the past but I think this will be our new go to in Jamaica. Looking foward to our next stay thank you "

Standalone villa surrounded by trees, with a gated entrance and a dirt driveway.

includes taxes & fees

24 Jul - 25 Jul

Stunning home with a charming garden and covered porch.

Relax by the ocean-view pool surrounded by a shaded deck.

"There isn’t a beach anywhere near the house."

includes taxes & fees

30 Jul - 31 Jul

Escape to a serene lakeside haven with a peaceful view of the water and distant mountains.

"Very quiet, felt very safe "

includes taxes & fees

24 Jul - 25 Jul

Relax on the ocean-facing terrace with unobstructed views, lounge chairs, and a dining table.

"Our group of 14 adults and 6 kids found KRP Villa to be the perfect property for our stay. Each family had their own room and private bathroom, which was essential for our group’s comfort.The villa’s outdoor space was a highlight—spacious, with plenty of seating and a large pool that comfortably accommodated everyone without ever feeling crowded.Chef Darren’s meals were a standout, transforming every dish into something memorable with his unique touch. The grounds staff, Ainsley and Foota, were...

Enjoy a serene beach experience with a clear view of the surrounding mountains.

includes taxes & fees

25 Jul - 26 Jul

Kitchen features a central island, stainless steel appliances, and a window with patterned curtains.

"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."

Enjoy breathtaking views of the coastline from this balcony.

"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!"

includes taxes & fees

24 Jul - 25 Jul

Enjoy a serene beach experience with a tranquil atmosphere, shaded areas, and opportunities for kayaking and paddleboarding.

"Needed a place for my family and mother in law and cousin. Was perfect for that size group. Loved the outdoor kitchen and being able to be on the water every morning."

Relax in this serene outdoor seating area with a view of the lush landscape and distant coastline.

"This is the most idyllic, amazing, beautiful paradise you will ever stay in. We cannot recommend this enough. Geneva and Shaun are the most wonderful hosts, we are definitely coming back !! We are devastated to be leaving. They are the loveliest people who took care of all our needs and took time to show us around their stunning property. She is also a great cook. What a lovely family. We will miss you.Thank you thank you thank you. Tonnes of love. "

includes taxes & fees

24 Jul - 25 Jul

Enjoy breathtaking views of the coastal landscape from this balcony.

"The rooms and pool are very good. Getting back down the steep and long drive during hours of darkness is difficult."

Relax by the infinity pool overlooking the serene ocean view, surrounded by lush greenery and palm trees.

"Just what the family needed. This will be an annual experience. "

Stunning building with a central arched window and classical balustrade.

"Great neighborhood. Safe environment. Awesome host"

Enjoy casual dining at the central island with bar stools, complemented by a large window.

Enjoy a refreshing swim in our outdoor pool.

"The views,the comfort, It was Safe that was beautiful it was up-to-date the staff was knowledgeable Of the environment shopping restaurants They were friendly always around if you needed them to the phone call away very private find for me and my husband Privite beach with your steps away Private parking private entrance security toiletries and bedding Very comfortable Can’t wait to stay again state for five days enjoyed every bit of it. I think we may good lifetime friends with the owner and...

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Top Woodstock Hotel Reviews

Indigo Beach Resort

10/10 Excellent

"This trip was the most life-changing experience! I truly enjoyed the amazing people that I've had the opportunity to encounter. The sense of peace that I felt there is unmatched. I remember and miss the beautiful sunsets and long walks on the beach. The ability to get lost in the moment. Thank you, Jamaica! The surroundings allowed me the opportunity to dream in a stress-free environment."

Comfort and stylish near Negril

10/10 Excellent

"This rental was absolutely fabulous. We have been going to Jamaica for 30 years. This was by far the best vacation we’ve had. The rental is spotless the owner Donna thought of everything that we would need including a basket of snacks and a case of water. The neighborhood is quiet and beautiful. The beach is five minutes away as well as a river to swim in. We enjoyed the privacy of this rental. The view of the ocean is stunning. The breeze off the ocean kept us comfortable, no need to turn on the air conditioning. I highly recommend this rental it is safe and beautiful. I would like to stay there forever! Definitely get breakfast included it was plentiful and delicious. Have questions, do not hesitate to ask the owner she is lovely. "

Luxury ocean view villa

10/10 Excellent

"This vacation was truely my best vacation in Jamaica and I have been there numerous times. The host greeted us warmly and she wasted no time in giving us a tour of her castle. Subsequently, she introduced us to some Jamaican exoctic fruits and pastries .we enjoyed her treats immensely. We also enjoyed the delicious dinner her Chef prepared for us.Her castle’s location overlooks the Caribbean Sea. The view from the balcony is breathtaking. This castle is spacious and every room is equipped with an air condition unit that adequately provide us comfort in a Caribbean setting. The kitchen is gigantic and is furnished with modern amenities. During the days, you have the option of staying indoor enjoying the AC or go outside into the pool that is surrounded by beautiful Jamaican flowers. We had a tremendous time and I am gleefully imploring any one who is considering staying at Marvettavile to do not hesitate because the booking there is on steroid. Security is top notch . Once again thank you Marvette for your hospitality."

Kassion Corner

2/10 Terrible

"As per email exchange with Hotels.com, we are trying to obtain a refund for this booking as, on arrival at the hotel, the gate was chained closed. We had kept trying to phone to confirm our ETA but the telephone number was unobtainable. The hotel did not attempt to contact us. We were very disappointed as the remote location really appealed to us."

Luna Sea Inn

8/10 Good

"The parking was easy and the hotel is in a lovely position surrounded by blue sea. We were warmly welcomed with complimentary bottles of water and a welcome rum punch or beer. We were also given an upgrade to a front facing room which was much appreciated. The super king sized bed was really comfortable. There was a large fridge, kettle and mugs provided, just take your own coffee. The shower had plenty of hot water. The air con unit is quiet and works well, it is peaceful and we slept really well. You get a lovely sunset which we enjoyed from the gazebo which is lit with fairy lights. Dinner and breakfast were both excellent in quality and the menus are really nice, although some of the ingredients may be missing (Greek salad minus the feta) The callaloo parcels were just divine! I wanted the chefs signature herb crusted chicken but was warned off by the waitress saying it would take an hour to cook. Instead we ordered chicken pasta and goat curry which then took over an hour and a half to arrive. By the time our main course arrived 2h after we’d initially sat down we were past wanting to eat much. The locals seem to know to order in advance so it is ready when they arrive. If we had stayed longer, we would have done that for breakfast and dinner. It was the only thing that we didn’t like, you do want to wait over an hour for breakfast."

Oceanfront Luxury Villa: Private Beach & Staff

10/10 Excellent

"This is a great vacation spot if you want to relax!! It’s a perfect setting to get away. Special thank you to Shane for making it a memorable experience. He prepared world class dinners with local flavors. He was extremely knowledgeable and helpful in planning day trips to black river by boat with a few stops to include pelican bar and a local crab shack on the river. He recommended YS falls for a day trip, beautiful! We did leave the villa to grab lunch at Jack sparrows and spend some time with the locals at treasure beach. The home is dated but has all the amenities. Mark the owner was also very responsive before the trip to finalize any questions. The housekeeper and gardener were there every morning working efficiently and gave great conversation . Thank you for a wonderful Jamaican experience "

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 €64 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?

“Something Blue” Entire property in Westmoreland, Jamaica Cozy 3 bedroom home: This highly rated holiday home rental in Woodstock offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Some other top choices in Woodstock are The Artist cabin is a mountain cabin overlooking the sea and coastline and Firefly cottage with Ocean view.

How many holiday rentals are there in Woodstock?

With 67 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.

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Holiday Rentals in Woodstock

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Holiday Rentals in Woodstock

Villa Serene Jewel of Black River 4 bedroom 5bathrooms

10BR Luxury Villa w/ Private Beach; Fully Staffed

Luxury ocean view villa

Oceanfront Luxury Villa: Private Beach & Staff

Villa Gilgal - Possibilities are endless.... Fully Staffed

Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!

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

Furnished Villa right on the beach!

Deano's Cottages

Oceanview lux Villa, infinity pool, swim up bar, chef services, perfect retreat!

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

Luxurious 3 beds, 2 bath with all amenities

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

Spectacular Private Beachfront Villa: Unwind in Paradise at our Beach House!

Firefly cottage with Ocean view

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

Award-winning villa with private beachfront and pool

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

A Cut Above The Rest

Double queen suite on the beach Private entrance

Top Woodstock Hotel Reviews

Indigo Beach Resort

Comfort and stylish near Negril

Luxury ocean view villa

Villa Gilgal - Possibilities are endless.... Fully Staffed

Indigo Beach Villa - Black River

Kassion Corner

Luna Sea Inn

Oceanfront Luxury Villa: Private Beach & Staff

Sandals South Coast - ALL INCLUSIVE Couples Only

Find out more about Woodstock

Frequently asked questions