Vacation rentals in Olive

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Olive

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Cottage in West Shokan

4.96 out of 5 average rating, 139 reviews

Catskills Blue House on Three Acre Site by Ashokan Reservoir

You have the whole house and three acres to enjoy. The two bedrooms are upstairs, with skylights and a bright, airy feel to them. The wood burning stove is an awesome way to make things cozy. There's also a firepit and grill you're welcome to use. Guests have complete access to the home and three-acre property. The garage on the property is inaccessible by guests. We're available to contact anytime. Hike, ski, swim, bike, do yoga, or whatever comes to mind— all is possible in the Catskills. The Ashokan reservoir bike/walk path is a few miles down the road. Not far the other way is Marty's Mercantile for coffee, lunch, and basic supplies. There's plenty of parking in the driveway. Don't expect to Uber while up here. Walk, bike, or ride a horse instead. :) There's plenty of parking in the driveway.

Apr 19 – 26

€ 290 per night
Guest favorite

Guesthouse in Accord

4.93 out of 5 average rating, 111 reviews

Studio in Private Forest; Peace and Solitude

Set in a hemlock forest on a quiet country road, this newly redone and separate guest studio is a perfect getaway. Set on 30 private wooded acres, the property is bisected by a Class A trout stream. Guests have access to the shared pool Mon-Fri, but not Sat-Sun. The second floor studio has a queen size bed and a queen size sofa bed along with a private bathroom. There is Wifi, a television (ROKU). There is no kitchen, however, we do provide a microwave, dorm fridge and Keurig coffee machine.

Apr 9 – 16

€ 93 per night
Guest favorite

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 298 reviews

Artful and Serene Woodstock Getaway

Please read description thoroughly before booking. Relax with a comfortable mix of rustic and elegant in this colorful studio with loft bedroom in the Catskill Mountains of NY. Midway between lovely towns, Woodstock and Phoenicia. Full kitchen and bath, cathedral ceiling, sleeps two adults comfortably. Due to allergies, we do not allow pets. This includes service animals. We use fragrance free laundry detergent. No smoking or vaping. This listing is not suitable for children or infants.

Jun 10 – 17

€ 124 per night

Popular amenities for Olive vacation rentals

Stay near Olive's top sights

Bread Alone Bakery156 locals recommend
Boiceville Supermarket117 locals recommend
Onteora Mountain House4 locals recommend
Marty's Mercantile32 locals recommend
Ashokan Rail Trail- Ashokan Station Trailhead9 locals recommend
Fruition Chocolate Works27 locals recommend

Other great vacation rentals in Olive

Guest favorite

Home in Kerhonkson

5.0 out of 5 average rating, 206 reviews

Cook House | Modern Cottage w/ Fireplace

Feb 12 – 19

€ 346 per night
Guest favorite

Home in Kingston

4.97 out of 5 average rating, 269 reviews

This New House

Feb 3 – 10

€ 151 per night
Superhost

Home in West Shokan

4.87 out of 5 average rating, 112 reviews

Watson House 1850

May 24 – 31

€ 231 per night
Guest favorite

Home in Kingston

4.96 out of 5 average rating, 255 reviews

Country Elegance with Beautiful Catskill Mt. Views

May 13 – 20

€ 164 per night
Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 634 reviews

Dutch Touch Woodstock Cottage

Nov 14 – 21

€ 132 per night
Guest favorite

Home in Kerhonkson

4.95 out of 5 average rating, 237 reviews

Architect's Hudson Valley Home in the Woods

May 4 – 11

€ 389 per night
Guest favorite

Guest suite in High Falls

4.94 out of 5 average rating, 104 reviews

Mohonk Preserve, Hudson Valley, Sunlit Apartment

May 18 – 25

€ 115 per night
Guest favorite

Cabin in Kerhonkson

4.98 out of 5 average rating, 118 reviews

Lovely Catskill Cabin w/Piano and free firewood

Nov 16 – 23

€ 182 per night
Guest favorite

Home in Mount Tremper

4.96 out of 5 average rating, 211 reviews

Overlook Creek Cottage 1 Near Phoenicia

Jan 15 – 22

€ 165 per night
Guest favorite

Home in Kerhonkson

4.94 out of 5 average rating, 325 reviews

Country House: Rustic Charm With Modern Feel

Sep 15 – 22

€ 617 per night
Guest favorite

Guest suite in Kerhonkson

4.96 out of 5 average rating, 124 reviews

Private Apt. in Vintage House steps to Kerhonkson.

May 5 – 12

€ 91 per night
Guest favorite

Guesthouse in Olive

5.0 out of 5 average rating, 51 reviews

The Lily Cottage Guesthouse

Sep 15 – 22

€ 130 per night

Quick stats about vacation rentals in Olive

Total rentals

200 properties

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

100 properties allow pets

Family-friendly rentals

150 properties are a good fit for families

Total number of reviews

14K reviews

Nightly prices starting at

€ 19 before taxes and fees

Frequently Asked Questions

  • How much does it cost to stay in cabin rentals in Olive?

    Experience the best of Olive with our cabin rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Olive have a kitchen?

    Absolutely! We offer over 90 house rentals with a kitchen in Olive. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Guesthouse Rentals in Olive?

    Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Olive?

    Yes! Work meets play with ease at over 130 vacation rentals in Olive featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Olive?

    Olive has more than 150 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Olive have wifi?

    Absolutely! We offer over 100 house rentals with wifi in Olive. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Olive have air conditioning?

    Absolutely! We offer over 90 house rentals with air conditioning in Olive. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Olive have free parking?

    Absolutely! We offer over 100 house rentals with free parking in Olive. Enjoy a tailored experience with all the comforts you desire.

  • Are there Olive vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Olive, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there pet-friendly vacation rentals in Olive?

    Four-legged friends are welcome in Olive. Choose from more than 100 vacation rentals for guests traveling with pets.

Destinations to explore

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