Olivebridge holiday homes

We found 1,527 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in Olivebridge that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the amenities that you need and want, such as air conditioning and a TV. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Olivebridge

Showing deals for:18 Dec - 25 Dec

Sunroom
Hot tub
Kitchen
Tannersville Farmhouse in the summer!
Exceptional
(90 reviews)

Start thinking about Fall Foliage! Hot tub, fabulous kitchen, views everywhere!

Tannersville

11% off
NZ$21,523
for 7 nights, 1 home
NZ$3,075 per night
includes taxes & fees
Start thinking about Fall Foliage! Hot tub, fabulous kitchen, views everywhere!
A beautiful spot for our comfortable cabin
Rear Deck, Hot Tub and Screened Porch
Property grounds
Open kitchen.
Exceptional
(119 reviews)

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Bearsville

8% off
NZ$5,422
for 7 nights, 1 cabin
NZ$775 per night
includes taxes & fees
Secluded Cabin with Hot Tub - 5 Miles to Woodstock
Living area
Exterior
Living area
Private kitchen
Exceptional
(16 reviews)

Cozy A FRAME ski retreat, walking distance into Hunter Mountain. New 2026 Rates

Hunter

8% off
NZ$4,880
for 7 nights, 1 chalet
NZ$697 per night
includes taxes & fees
Cozy A FRAME ski retreat, walking distance into Hunter Mountain. New 2026 Rates
Dining
Terrace/patio
Exterior
Living area
Exceptional
(31 reviews)

Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!

Hurley

12% off
NZ$3,266
for 7 nights, 1 cabin
NZ$467 per night
includes taxes & fees
Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!
The stocked kitchen comes with a Keurig, a Mr. Coffee, and kettle
The hot tub leads to the deck, and is great to use year round
Interior
Interior
Exceptional
(114 reviews)

Mountain View Chalet Near Skiing

Hensonville

12% off
NZ$9,424
for 7 nights, 1 home
NZ$1,346 per night
includes taxes & fees
Mountain View Chalet Near Skiing
Exterior
Terrace/patio
Interior
Great room
Exceptional
(119 reviews)

SECLUDED-PRIVATE LUXURY ESCAPE 5BR•4BA JACUZZI -ARCADE GAME RM WINDHAM HUNTER

Jewett

8% off
NZ$8,530
for 7 nights, 1 home
NZ$1,219 per night
includes taxes & fees
SECLUDED-PRIVATE LUXURY ESCAPE 5BR•4BA JACUZZI -ARCADE GAME RM WINDHAM HUNTER
Dining
Living area
Dining
Living area
Exceptional
(127 reviews)

Modern, Artsy, & Lofty Log Home

Wallkill

21% off
NZ$16,327
for 7 nights, 1 home
NZ$2,332 per night
includes taxes & fees
Modern, Artsy, & Lofty Log Home
Interior
Exterior
Living area
Private kitchen
Exceptional
(33 reviews)

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Hunter

8% off
NZ$2,732
for 7 nights, 1 chalet
NZ$390 per night
includes taxes & fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Living area
Exterior
Outdoor dining
Pool
Exceptional
(49 reviews)

Secluded family retreat within minutes of Woodstock village

Saugerties

8% off
NZ$5,741
for 7 nights, 1 home
NZ$820 per night
includes taxes & fees
Secluded family retreat within minutes of Woodstock village
Living area
Room
Living area
Outdoor dining
Exceptional
(7 reviews)

Cozy and bright 2-bedroom cabin in charming Elka Park

Tannersville

8% off
NZ$3,462
for 7 nights, 1 cabin
NZ$495 per night
includes taxes & fees
Cozy and bright 2-bedroom cabin in charming Elka Park
Indoor pool with awesome views
Private kitchen
Award winning design, European alpine with symmetric glass walls front and back
Main living room with expansive windows and views
Exceptional
(10 reviews)

*The View* ski in/out modern luxury at Windham Mountain Resort

Windham

9% off
NZ$47,186
for 7 nights, 1 home
NZ$6,741 per night
includes taxes & fees
*The View* ski in/out modern luxury at Windham Mountain Resort
Dining
Another property we have down the street; 4bedrm;3bath with large loft&game room
Spacious living room; open to dining area
Exterior
Exceptional
(80 reviews)

Heart of Hunter Village; across MT!Spring Special3rd night half OFF!” W/weekend

Hunter

8% off
NZ$6,365
for 7 nights, 1 home
NZ$909 per night
includes taxes & fees
Heart of Hunter Village; across MT!Spring Special3rd night half OFF!” W/weekend
Front Entry
Outdoor dining
Interior
Exterior detail
Exceptional
(10 reviews)

Church Des Artistes a Hudson Valley retreat

Kingston

8% off
NZ$21,970
for 7 nights, 1 home
NZ$3,139 per night
includes taxes & fees
Church Des Artistes a Hudson Valley retreat
Interior
Living area
Tastefully decorated for the holidays
Luxury bedding
Exceptional
(17 reviews)

Located within 10 minutes from both Windham Mountain and Hunter Mountain!

Jewett

8% off
NZ$7,953
for 7 nights, 1 home
NZ$1,136 per night
includes taxes & fees
Located within 10 minutes from both Windham Mountain and Hunter Mountain!
Private, luxurious retreat in the heart of an organic farm in the Hudson Valley
450sqft of living space: super comfy kingsize bed (+ 2 optional twin beds)
You are welcome to fish, swim, or paddleboard in our 2 acre pond
Enjoy your private deck, lawn, firepit, and grill!
Exceptional
(26 reviews)

Luxury retreat w/ private deck, garden, firepit on organic farm

Gardiner

8% off
NZ$2,973
for 7 nights, 1 cabin
NZ$425 per night
includes taxes & fees
Luxury retreat w/ private deck, garden, firepit on organic farm
stay warm & cozy by the fireplace with large screen TV above
Sit stream side and enjoy the beauty of nature and our (seasonal) fire pit
bluestone, more shaded patio with shade garden
The fall foliage is gorgeous right in "your own" backyard!!
Exceptional
(163 reviews)

Sanctuary by the Stream

Phoenicia

13% off
NZ$3,540
for 7 nights, 1 home
NZ$506 per night
includes taxes & fees
Sanctuary by the Stream
Property grounds
Property grounds
Room
Interior
Exceptional
(17 reviews)

Hudson Valley’s Private Waterfront Camping Getaway

Lake Katrine

8% off
NZ$2,750
for 7 nights, 1 unit
NZ$393 per night
includes taxes & fees
Hudson Valley’s Private Waterfront Camping Getaway
Kitchen comes fully stocked with pots/pans, dishes, silverware, glasses, etc.
Your primary entrance will lead you directly in the homes cool kitchen!
Interior
130 year old stone fireplace in green living room
Exceptional
(88 reviews)

Featured on MTV ! You Have To See It To Believe It ! Unlike any other !

Haines Falls

8% off
NZ$12,114
for 7 nights, 1 home
NZ$1,731 per night
includes taxes & fees
Featured on MTV ! You Have To See It To Believe It ! Unlike any other !
Interior
Room
Dining
Property grounds
Exceptional
(86 reviews)

for the creative spirit, swimming dock on pond, horses to pet, Fire pit

Ulster Park

8% off
NZ$3,987
for 7 nights, 1 home
NZ$570 per night
includes taxes & fees
for the creative spirit, swimming dock on pond, horses to pet, Fire pit
Vaulted Great Room
Property grounds
Interior
Property grounds
Exceptional
(13 reviews)

The Blue House on the Hill Catskills—VIEWS

Claryville

16% off
NZ$4,160
for 7 nights, 1 home
NZ$594 per night
includes taxes & fees
The Blue House on the Hill Catskills—VIEWS
Living area
Exterior
Property grounds
Private kitchen
Exceptional
(10 reviews)

Most Charming, Most quiet place in the Catskills--Willow-brook Cottage

Lake Hill

8% off
NZ$3,752
for 7 nights, 1 cabin
NZ$536 per night
includes taxes & fees
Most Charming, Most quiet place in the Catskills--Willow-brook Cottage
Exterior detail
Property grounds
Living area
Living area
Exceptional
(13 reviews)

"Frank Lloyd Wright" Catskills Mountain Yoga-Spa Retreat on 15 Acres

Mount Tremper

12% off
NZ$10,921
for 7 nights, 1 home
NZ$1,560 per night
includes taxes & fees
"Frank Lloyd Wright" Catskills Mountain Yoga-Spa Retreat on 15 Acres
Dining
Exterior
Interior
Private kitchen
Exceptional
(10 reviews)

Mohonk's Peaceful 5BR-3BA~Jacuzzi~Huge Deck~Right On Coxing Kill~ Private Road

High Falls

16% off
NZ$8,474
for 7 nights, 1 home
NZ$1,211 per night
includes taxes & fees
Mohonk's Peaceful 5BR-3BA~Jacuzzi~Huge Deck~Right On Coxing Kill~ Private Road
In winter, stay toasty warm by the fire
Welcome to Bridge House
Large sliders bring nature indoors
Fern garden in summer
Exceptional
(128 reviews)

Waterfront Mid-century Modern Gem Surround by Forever Wild Land

Willow

8% off
NZ$4,391
for 7 nights, 1 home
NZ$627 per night
includes taxes & fees
Waterfront Mid-century Modern Gem Surround by Forever Wild Land

  • 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

Why people love visiting relaxing Olivebridge

Enjoy the entertainment and other features of Olivebridge. This relaxing city is known for its hiking, skiing and mountain views. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Olivebridge

Do you want to find attractions to see while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Olivebridge a fun spot to go on holiday. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mohonk Golf Course (11.1 mi / 17.9 km)
  • Straus Center - Frost Valley YMCA (13.4 mi / 21.6 km)
  • Robibero Winery (15 mi / 24.1 km)
  • Indian Head Mountain (15.4 mi / 24.8 km)
  • Belleayre Mountain Ski Center (20.8 mi / 33.5 km)
  • Woodstock Golf Club (9.3 mi / 14.9 km)

Exploring the natural landscape of Olivebridge

Whether you're looking for adventure or just want to spend some time taking in the scenery, Olivebridge is a great place to get outside. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Ashokan Rail Trail- Woodstock Dike Trailhead (7.8 mi / 12.6 km)
  • Slide Mountain (10.1 mi / 16.2 km)
  • Esopus Creek (10.2 mi / 16.4 km)
  • Overlook Mountain Trailhead (11 mi / 17.7 km)
  • Mohonk Lake (11.6 mi / 18.6 km)
  • Giant Ledge Trailhead (11.8 mi / 19 km)

Travelling to and around Olivebridge

Fly into Newburgh, NY (SWF-Stewart Intl.), the closest airport, located 30.3 mi (48.8 km) from the city centre.

Frequently asked questions

Where are the best Olivebridge ski resort rentals?
For the best ski resort rentals near Olivebridge, New York, travellers should consider the nearby Hunter Mountain area, located about a 30-minute drive away. Hunter Mountain offers a variety of holiday rentals, including cozy chalets and spacious cabins, which are superb for families or groups seeking a comfortable stay close to the slopes. Many of these properties come equipped with amenities like full kitchens, private decks with mountain views, and even fireplaces to warm up after a day of skiing.In the picturesque village of Tannersville, just a short drive from the ski resort, visitors can find charming lodgings that capture the essence of the Catskills. These accommodations often feature rustic decor, outdoor spaces for enjoying the fresh mountain air, and convenient access to local shops and eateries. Some properties may also include amenities such as hot tubs or fire pits, ideal for unwinding in the evenings.Additionally, the surrounding area offers plenty of opportunities for outdoor activities beyond skiing. The nearby Kaaterskill Falls and the scenic trails in the Catskill Park provide excellent options for hiking and enjoying nature.
What is the most popular type of holiday rental accomodation in Olivebridge?
In Olivebridge, holiday houses are the most popular type of holiday rental, with around 27 available in this charming area. These properties typically offer spacious interiors, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also feature outdoor spaces such as decks or gardens, superb for enjoying the serene surroundings after a day of exploring the nearby Catskill Mountains or the picturesque Ashokan Reservoir. Additionally, there are several cottages and cabins that provide a rustic charm and a closer connection to nature, offering amenities like fireplaces and cosy living areas.
Are there any family house rentals in Olivebridge?
In Olivebridge, New York, there are several family-friendly house rentals available, making it an excellent choice for families seeking a relaxing getaway. The area is surrounded by the stunning natural beauty of the Catskill Mountains, providing ample opportunities for outdoor activities such as hiking and exploring nearby state parks. Many of these homes feature spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces superb for children to play.Visitors can enjoy amenities like Wi-Fi, air conditioning, and sometimes even private gardens or decks where families can relax together after a day of adventure.
Can I rent a holiday home with a pool or hot tub in Olivebridge?
In Olivebridge, there are several holiday homes available for rent that come with pools or hot tubs, making it a lovely choice for travellers seeking relaxation amidst nature. This picturesque area, located in the scenic Hudson Valley, offers a tranquil escape with beautiful views of the surrounding mountains and forests.Many of the properties feature private outdoor pools, hot tubs, and spacious decks ideal for enjoying the serene environment. Inside, guests can expect comfortable living spaces, fully equipped kitchens, and amenities such as Wi-Fi and air conditioning to ensure a pleasant stay.
Are there pet-friendly house rentals in Olivebridge?
In Olivebridge, there are a number of pet-friendly house rentals available, making it a suitable destination for travellers with pets. Many of these holiday homes are located in scenic locations, offering amenities such as spacious yards, fully equipped kitchens, and comfortable living areas, providing a cozy feel for both guests and their furry companions.The area is surrounded by beautiful natural landscapes, including the nearby Catskill Mountains, which offer numerous hiking trails and outdoor spaces superb for walking dogs. Additionally, the Ashokan Reservoir, located a short drive away, features trails that are ideal for leisurely strolls with pets, allowing visitors to enjoy the stunning views while exploring the outdoors.
Are there any remote work holiday rentals in Olivebridge?
In Olivebridge, there are numerous remote work-friendly holiday rentals available, with around 42 properties to choose from. This picturesque area in the heart of the Catskills offers a serene environment superb for remote work while enjoying nature. Many of these rentals come equipped with essential amenities such as Wi-Fi, dedicated workspaces, and comfortable desks, making it easy to stay productive during your stay. Some properties may even feature additional conveniences like computer monitors and printers, catering specifically to those looking to combine work with leisure.The region is known for its stunning landscapes, including nearby hiking trails and the scenic Ashokan Reservoir, providing excellent opportunities for outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Olivebridge?
In Olivebridge, popular rental amenities include fully equipped kitchens, allowing guests to prepare their meals with ease. Many properties also feature decks or patios, providing lovely outdoor spaces to relax and enjoy the natural surroundings. A blender is often available for those who enjoy making smoothies or other blended drinks. Some rentals come with a dedicated desk, ideal for guests who need to catch up on work or study during their stay. Additionally, a fireplace is a sought-after amenity, offering a warm and inviting atmosphere, especially during the cooler months.
When is the best time to visit Olivebridge for a holiday rental?
The best time to visit Olivebridge for a holiday rental is during the peak season of June to August, with July being particularly popular among travellers. This vibrant period attracts outdoor enthusiasts who relish the area's natural beauty and myriad activities. With warm temperatures averaging between 20 to 30 degrees Celsius, it's an ideal time for hiking, kayaking, and enjoying the lush landscapes that the Catskills have to offer.During these summer months, visitors can engage in the local culture and partake in various events and festivals that celebrate the region's charm. Olivebridge's picturesque setting provides ample opportunities for exploration, whether you're wandering through the scenic trails of the nearby Minnewaska State Park or enjoying a leisurely afternoon by the water.If you're looking for a more budget-friendly option, consider planning your trip in December. Although this month is quieter, it offers a unique opportunity to experience the tranquillity of Olivebridge during winter. The area transforms into a serene wonderland, great for cozy getaways and enjoying the peaceful surroundings.Ultimately, your ideal time to visit Olivebridge will depend on whether you prefer the lively option of summer or the peaceful beauty of winter.
What are the top attractions in Olivebridge?
In Olivebridge, visitors can enjoy a serene escape amidst nature, with several attractions that highlight the area's natural beauty. The nearby Minnewaska State Park Preserve offers stunning views, hiking trails, and picturesque waterfalls, making it a favourite for outdoor enthusiasts. The park features a variety of trails suitable for all skill levels, allowing visitors to explore the breathtaking landscapes of the Shawangunk Ridge.Additionally, the area is known for its charming local art scene, with galleries and studios that showcase the work of local artists. The historic Ashokan Reservoir, located just a short drive away, provides opportunities for fishing, kayaking, and picnicking, with beautiful vistas of the surrounding mountains.For those interested in local history, the Olivebridge area is home to quaint, historic buildings and the remnants of the region's storied past, which can be explored through scenic drives or leisurely walks.
Are all fees included in the Olivebridge holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Olivebridge holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Olivebridge with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Olivebridge holiday homes?
You can find great discounts on holiday homes in Olivebridge on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Olivebridge holiday home booking on Bookabach?
To find Olivebridge holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Olivebridge?
A long-stay holiday home in Olivebridge is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Olivebridge holiday home?
Book your Olivebridge holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Olivebridge?
Prices for holiday homes in Olivebridge vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Olivebridge to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.