Town of Olive holiday rentals

We found 666 holiday rentals — enter your dates for availability

Select from 21 homes, 12 cottages and other holiday rentals in Town of Olive to find one that's perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you expect for your stay, including air conditioning and cable TV. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Choose a holiday rental for your Town of Olive getaway

Learn about the unique charm of Town of Olive with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Town of Olive

Do you want to discover attractions to visit in the area? Venture out of your cosy holiday rental and check out everything that makes Town of Olive a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Woodstock Golf Club (9.2 mi / 14.8 km)
  • Straus Center - Frost Valley YMCA (12 mi / 19.2 km)
  • Mohonk Golf Course (12.8 mi / 20.5 km)
  • Hunter Mountain (17.7 mi / 28.5 km)
  • Belleayre Mountain Ski Center (18.4 mi / 29.7 km)
  • Belleayre Mountain Ski Center (19 mi / 30.6 km)

Exploring the natural features in Town of Olive

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Town of Olive. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Ashokan Rail Trail- Woodstock Dike Trailhead (8.4 mi / 13.5 km)
  • Catskill Mountains (8.5 mi / 13.6 km)
  • Overlook Mountain Trailhead (10.6 mi / 17 km)
  • Esopus Creek (11.5 mi / 18.5 km)
  • Opus 40 (12.9 mi / 20.8 km)
  • Mohonk Lake (13.1 mi / 21.2 km)

Frequently asked questions

What is the best area to stay in Town of Olive when booking a holiday home?
If you’re organising a getaway to Town of Olive, Olivebridge is one of the most popular locations to stay. Whether you prefer a chalet, cottage or other property style, you’ll always have the whole place to yourself.
What is the most popular type of holiday home accommodation in Town of Olive?
According to our research, houses are the most sought-after type of property in Town of Olive. But of course, everyone’s idea of an awesome stay differs. Stayz has holiday homes of all shapes, sizes and budgets, so you’re sure to discover your ideal match.
How much does it cost to rent a holiday home in Town of Olive?
Length of stay, property type and time of year are some things that can affect the price of a holiday home. Simply add your travel dates to find your perfect fit. From comfy cabins to sprawling villas, all Stayz holiday homes provide incredible value.
How much does it cost to rent a beach house in Town of Olive?
When you travel and the size and style of the property will influence the cost of your beachside stay. Type in your Town of Olive travel dates to view your available options on Stayz. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to choose the features and amenities you want in your home.
Are there pet-friendly holiday homes in Town of Olive?
With 31 holiday homes that welcome four-legged guests, your happy hound can join in on your Town of Olive break. Use the filter tool to search our pet-friendly holiday homes and find a stay that’s pawfect on Stayz.
Can I rent a house with a pool in Town of Olive?
Mark the “pool” box in our handy filter tool and take your pick of seven houses with private pools in Town of Olive on Stayz. Morning soak, afternoon splash or midnight swim? Leisure time is up to you when your holiday property comes with a swimming pool.
What are popular home amenities in Town of Olive?
The most popular home amenities people are searching for in Town of Olive are a fireplace, a barbecue grill and tennis. Whether you’re on a trip with buddies, family or even pets, Stayz holiday homes provide the best amenities for chilling out with the people you love.
Are there large group holiday homes in Town of Olive?
Town of Olive has nine holiday homes that can accommodate 10 or more people. These properties come with plenty of space to share good times with your favourite people.
Are there holiday homes in Town of Olive that welcome kids?
Town of Olive has 31 family-friendly holiday homes. And booking a stay that welcomes youngsters is simple with our “Properties good for families” filter. In addition to having the entire place to yourselves, you’ll also get access to perks and amenities like extra bedrooms, kitchens and yards.
What are the top attractions for families in Town of Olive?
Keep your kids busy at these fantastic family-friendly attractions in Town of Olive:

  • Catskill Mountains
  • Ashokan Rail Trail- Woodstock Dike Trailhead
  • SweetHeart Gallery

Are there one-bedroom holiday homes in Town of Olive?
Take your pick from five one-bedroom homes in Town of Olive. Whether you want a cosy cottage or a cabin, our one-bedroom homes are perfect if you don’t need lots of room. One of the best parts about having your own place? You won’t ever need to share your trip with strangers.
Can I find two-bedroom holiday homes in Town of Olive?
Take off with your loved ones and enjoy a relaxing escape in one of the eight two-bedroom holiday properties Town of Olive has to offer.
Are there holiday homes with WiFi in Town of Olive?
Town of Olive has 19 holiday homes with WiFi, so you can stay connected during your trip. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming Hollywood blockbusters to catching up on social media, these Stayz homes will keep you online.
How can I find holiday homes with air conditioning in Town of Olive?
Town of Olive has 29 holiday homes where you’ll be able to spend your days in air-conditioned comfort. To locate a property on Stayz that has this amenity, enter your travel dates and use the convenient filters to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Town of Olive?
You should check with the Town of Olive holiday property you’re considering on Stayz as the age limit differs. However, generally it’s 16, 18 or 21.
How long can I rent a holiday home in Town of Olive for?
The length of time you can book a holiday home in Town of Olive differs according to the property. Simply enter your desired dates to look at a list of options offering extended stays. With lots of amenities such as air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you’re sure to find someplace just right to call your home away from home in Town of Olive.

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