A mountainous landscape with autumn foliage.

Town of Olive holiday rentals

We found 710 holiday rentals — enter your dates for availability

Select from 17 homes, 13 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.

Popular Town of Olive destinations on Stayz

A large lake with a bridge, surrounded by mountains and greenery.

Olivebridge

Holiday rentals with weekly discounts – Town of Olive

Showing deals for:18 Dec - 25 Dec

A beautiful spot for our comfortable cabin

Exceptional

(119 reviews)

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Bearsville

8% off

AU$4,354

for 7 nights, 1 cabin

AU$622 per night

includes taxes & fees

Exceptional

(31 reviews)

Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!

Hurley

12% off

AU$2,624

for 7 nights, 1 cabin

AU$375 per night

includes taxes & fees

Exceptional

(49 reviews)

Secluded family retreat within minutes of Woodstock village

Saugerties

8% off

AU$4,614

for 7 nights, 1 home

AU$659 per night

includes taxes & fees

Exceptional

(13 reviews)

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

Mount Tremper

12% off

AU$8,778

for 7 nights, 1 home

AU$1,254 per night

includes taxes & fees

new, beautiful, fully equipped, large, custom kitchen-plenty of counter space.

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

AU$2,901

for 7 nights, 1 home

AU$414 per night

includes taxes & fees

Exceptional

(10 reviews)

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

High Falls

16% off

AU$6,842

for 7 nights, 1 home

AU$977 per night

includes taxes & fees

Exceptional

(13 reviews)

The Blue House on the Hill Catskills—VIEWS

Claryville

16% off

AU$3,382

for 7 nights, 1 home

AU$483 per night

includes taxes & fees

Cooking is a breeze in this recently remodeled kitchen

Exceptional

(128 reviews)

Waterfront Mid-century Modern Gem Surround by Forever Wild Land

Willow

8% off

AU$3,529

for 7 nights, 1 home

AU$504 per night

includes taxes & fees

Great room featuring a wonderful wall of windows

Exceptional

(52 reviews)

Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres

Woodstock

12% off

AU$5,999

for 7 nights, 1 home

AU$857 per night

includes taxes & fees

Exceptional

(10 reviews)

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

Lake Hill

8% off

AU$3,015

for 7 nights, 1 cabin

AU$431 per night

includes taxes & fees

Screened-in porch with woodland views, elegant seating & peaceful ambiance.

Wonderful

(7 reviews)

Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

Woodstock

16% off

AU$4,044

for 7 nights, 1 cottage

AU$578 per night

includes taxes & fees

Eat-in country kitchen with all appliances, including dishwasher and microwave.

View #1 of deck with mountain in background

One side of romantic master bedroom with pink chaise and king size bed.

Exceptional

(46 reviews)

Beautiful large Woodland Valley/Phoenicia post & beam cabin with seasonal stream

Phoenicia

8% off

AU$3,405

for 7 nights, 1 home

AU$486 per night

includes taxes & fees

Exceptional

(26 reviews)

Incredible Lake House with Stunning Mountain Views (swimming lake)

Chichester

8% off

AU$5,682

for 7 nights, 1 home

AU$812 per night

includes taxes & fees

Rock Maple countertops and KitchenAid refrigerator with through-the-door ice

Dining room seats eight to ten - extra chairs available

Exceptional

(92 reviews)

1878 Farmhouse near Phoenicia/Fast Wi-Fi - 10 minutes from Belleayre Mt.

Shandaken

21% off

AU$2,859

for 7 nights, 1 home

AU$408 per night

includes taxes & fees

Exceptional

(11 reviews)

Stone Ridge Stunner

Stone Ridge

19% off

AU$2,407

for 7 nights, 1 home

AU$344 per night

includes taxes & fees

Porch in winter (floor to ceiling screens in summer)

Exceptional

(11 reviews)

Cozy modern home on 14 acres of woods

Accord

8% off

AU$4,454

for 7 nights, 1 home

AU$636 per night

includes taxes & fees

The backyard with hammock, fire pit, and waterfall. View from the deck.

Exceptional

(8 reviews)

Airy 3BR on the banks of a roaring creek

Kerhonkson

11% off

AU$2,879

for 7 nights, 1 home

AU$411 per night

includes taxes & fees

Exceptional

(12 reviews)

Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia

Phoenicia

8% off

AU$2,381

for 7 nights, 1 cottage

AU$340 per night

includes taxes & fees

Exceptional

(7 reviews)

Charming 3-bedroom bungalow with AC in Phoenicia, Catskills

Phoenicia

8% off

AU$3,826

for 7 nights, 1 home

AU$547 per night

includes taxes & fees

Pool is open Memorial Day through Labor Day.

Covered 15' picnic table for enjoying meals al fresco.

Sun room - Sofa converts to full-size bed & doors close to make a cozy bedroom.

Exceptional

(7 reviews)

Experience the Catskills - Explore, Entertain and Relax at our Chalet.

Lanesville

16% off

AU$4,072

for 7 nights, 1 home

AU$582 per night

includes taxes & fees

Exceptional

(31 reviews)

Enjoy the peace & quiet on 40 private acres of secluded forest.

Accord

6% off

AU$2,927

for 7 nights, 1 home

AU$418 per night

includes taxes & fees

Exceptional

(44 reviews)

Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby

Phoenicia

17% off

AU$1,879

for 7 nights, 1 apartment

AU$268 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - Town of Olive

Stylish Mountain House with Reservoir Views, Near Woodstock NY

Sleeps 6 · 3 bedrooms · 3+ bathrooms

Ashokan ArtHaus, Private Hot Tub, Wags Welcome!

Sleeps 5 · 2 bedrooms · 1 bathroom

Catskills Mountain Ski Retreat with amazing views

Sleeps 10 · 4 bedrooms · 4 bathrooms

Secluded Catskill Mountains Getaway Peaceful Nature Near Woodstook

Sleeps 3 · 1 bedroom · 2 bathrooms

Premier Host

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Sleeps 2 · 1 bedroom · 1 bathroom

Premier Host

Relaxing Catskill Mountain Cottage.

Sleeps 4 · 2 bedrooms · 1 bathroom

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:

Straus Center - Frost Valley YMCA (12 mi / 19.2 km)
Mohonk Golf Course (12.8 mi / 20.5 km)
Indian Head Mountain (14.8 mi / 23.9 km)
Robibero Winery (16.5 mi / 26.5 km)
Hunter Mountain (17.7 mi / 28.5 km)
Mountain Trails Cross Country Ski and Snowshoe Center (18 mi / 28.9 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:

Slide Mountain (8.3 mi / 13.3 km)
Ashokan Rail Trail- Woodstock Dike Trailhead (8.4 mi / 13.5 km)
Giant Ledge Trailhead (10 mi / 16.1 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)

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.

More holiday ideas

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