Vacation rentals in Olive

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Top-rated vacation rentals in Olive

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Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 638 reviews

Dutch Touch Woodstock Cottage

The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.

Nov 22 – 29

G$27,285 GYD per night

Guest favorite

Guesthouse in Accord

4.93 out of 5 average rating, 114 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.

May 12 – 19

G$18,844 GYD per night

Guest favorite

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 300 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.

Aug 8 – 15

G$25,443 GYD per night

Guest favorite

Barn in Stone Ridge

4.93 out of 5 average rating, 247 reviews

Hudson Valley Botanical Garden Rental

Located in Upstate New York on the edge of our Botanical Garden in the Lower Hudson Valley the "Barnette" is for nature lovers. This newly built repurposed barn is perfect for relaxing, exploring nature, and getting away from it all. Nearby are lots of hiking, rail trails, and farms. We are within driving distance of the Mohonk Mountain House, Minnewaska, Catskill Mountains, and a 2 hour drive from Manhattan. For winter enthusiasts there’s places to snowshoe, ski, and hike 20-60 minutes away.

Nov 10 – 17

G$33,481 GYD per night

Guest favorite

Cottage in Accord

4.87 out of 5 average rating, 215 reviews

Sweet Cottage on a Farm Road

Simple, airy, studio cottage next to my house, featuring a woodstove & enormous bathroom with a clawfoot tub. Perfect for writers/solo-travelers seeking solitude & peace and couples wanting quality time together. The cottage is on a scenic country road, walking distance to 3 farms, including 2 great farm-to-table restaurants: Westwind Pizza/Apple Orchard, Arrowood Brewery, & Hollengold Farm. A stone's throw are Stonehill Barn and Inness. 15 min drive to the incomparable Minnewaska State Park.

May 11 – 18

G$16,625 GYD per night

Guest favorite

Guesthouse in Woodstock

4.95 out of 5 average rating, 301 reviews

Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace

Snuggle by a roaring fire. Eat in a corner nook or at a rustic wooden counter by a window. This quaint, whimsical home has a private deck w/bbq, a garden with a hammock and fire pit. A full size Murphy bed with a full kitchen (except for an oven). You will have access to the entire guest house. A short drive to the beautiful, eclectic, funky town of Woodstock. Art & culture, restaurants, hiking & biking all nearby. Electric heat, ceiling fan, a standing ac unit and single person shower.

Feb 7 – 14

G$30,027 GYD per night

Guest favorite

Cabin in Kerhonkson

5.0 out of 5 average rating, 305 reviews

The Metsämökki - A Finnish Cabin in the Woods

The Metsämökki is a small Finnish cabin in the foothills of the Catskill Mountains. Originally a sauna that was shipped here from Finland. We renovated it to a tiny house that offers complete privacy. Enjoy the babbling brook while sitting on the deck and taking in the surrounding nature. We're not offering high-tech or glamour but this cabin is a beautiful retreat from the busy city. **Check out our new midweek discounted rates and enjoy a little extra time for a great price!!

Sep 4 – 11

G$28,555 GYD per night

Guest favorite

Guesthouse in Olivebridge

4.97 out of 5 average rating, 224 reviews

Black Olive Cabin in the Woods - Secluded, Tiny

The cabin is nestled into a mossy rock ledge covered with ferns in a secluded part of the Catskills just south of the Ashokan Reservoir. Constructed of large reclaimed hemlock beams and charred cedar siding on the outside, the cabin mixes the old with the new. The open concept design includes high ceilings, hardwood floors, a wood stove, lofted sleeping quarters, a full bathroom, and a kitchen with an induction cooktop and convection oven. It's the perfect weekend getaway.

Jul 20 – 27

G$31,693 GYD per night

Guest favorite

Cottage in Kerhonkson

4.91 out of 5 average rating, 375 reviews

Home Alone Woods

Small and charming cottage in quiet and secluded place surrounded by woods and nature with the hiking trails half a mile away. There is easy access to Hunter Mountain, Minnewaska State Park, Shawangunks, and many hiking trails. This is a perfect getaway for nature and outdoor enthusiasts, bikers, hikers, climbers, and skiers or people who look for peace and tranquility in the woods.The kitchen is equipped with cooking essentials such as pots, pans, and utensils.

Nov 29 – Dec 6

G$28,685 GYD per night

Guest favorite

Guesthouse in Mount Tremper

4.91 out of 5 average rating, 322 reviews

Cozy Catskill Cottage Perfect Getaway for Two

NEWLY RENOVATED, COZY, CLEAN, PRIVATE AND SECURE Cottage in scenic and peaceful locale. Convenient and easy to find near the town of Phonecia, NY. 100 PACES to the ESOPUS RIVER and its trout fishing, trail heads and scenic hikes less than a mile away. Close to numerous sophisticated dining and shopping options. Less than 30 minutes to BelleAyre and Hunter Summer Happenings. Perfect for couples who need a weekend country getaway.

Jul 31 – Aug 7

G$32,059 GYD per night

Guest favorite

Cabin in Olivebridge

4.93 out of 5 average rating, 426 reviews

Cozy Catskill Cabin on Acorn Hill

Enjoy a rustic respite from the city in this cozy cabin on 3.5 acres near the beautiful Ashokan reservoir and Catskill Park. Perfect for a relaxing weekend and as a hub for skiing and hiking. Cabin includes 1 bedroom and one bath, full kitchen, and living room with piano. This is a perfect get-away to relieve the stress of the city. Full amenity details are available in the listing. Town of Olive Registration # STR-22-19

Dec 30 – Jan 6

G$38,634 GYD per night

Guest favorite

Cottage in Shokan

4.9 out of 5 average rating, 240 reviews

Catskills 2 br Cottage

This sunny, 2br 1.5 bath cottage is perched on a mountainside, so you can enjoy the seasonal view of the Catskill Mountains and the Ashokan Reservoir as you bask in the warmth of the woodstove and cook great meals in the fully equipped kitchen. Located on a quiet, dead-end road, it is close to Woodstock and Phoenicia and less than 30 minutes from skiing at Belleayre. Just a 2-hour drive from NYC!

Jun 16 – 23

G$27,720 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Olive vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Olive's top sights

Bread Alone Bakery156 locals recommend

Boiceville Supermarket117 locals recommend

Ashokan Rail Trail- Boiceville Bridge Trailhead52 locals recommend

Onteora Mountain House4 locals recommend

Marty's Mercantile32 locals recommend

Ashokan Rail Trail- Ashokan Station Trailhead9 locals recommend

Other great vacation rentals in Olive

Guest favorite

Home in Kingston

4.97 out of 5 average rating, 275 reviews

This New House

Mar 22 – 29

G$30,106 GYD per night

Guest favorite

Home in Kerhonkson

5.0 out of 5 average rating, 211 reviews

Cook House | Modern Cottage w/ Fireplace

Apr 8 – 15

G$69,322 GYD per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 677 reviews

Victorian Haven

Feb 9 – 16

G$27,368 GYD per night

Guest favorite

Cottage in Olivebridge

4.91 out of 5 average rating, 116 reviews

Highpoint House: historic farmhouse on four acres

Aug 24 – 31

G$60,719 GYD per night

Guest favorite

Cottage in West Shokan

4.91 out of 5 average rating, 159 reviews

Relaxing Cottage in the Catskill Mountains

Mar 21 – 28

G$63,557 GYD per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 741 reviews

Hudson Valley Tiny House

Jul 5 – 12

G$22,908 GYD per night

Guest favorite

Cottage in Kerhonkson

4.94 out of 5 average rating, 255 reviews

Blue Haven in the Catskills

Aug 11 – 18

G$21,862 GYD per night

Guest favorite

Apartment in High Falls

4.98 out of 5 average rating, 112 reviews

Sunset Garden Room in High Falls

Jul 5 – 12

G$23,859 GYD per night

Show all

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
15K reviews
Nightly prices starting at
G$4,169 GYD before taxes and fees

Frequently Asked Questions

How much does it cost to stay in cottage rentals in Olive?
Experience the best of Olive with our cottage rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Olive have a kitchen?
Absolutely! We offer over 20 cottage rentals with a kitchen in Olive. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cottage Rentals in Olive?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with a kitchen, over 20 homes with wifi, over 20 homes with air conditioning, 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 cottage rentals in Olive have wifi?
Absolutely! We offer over 20 cottage rentals with wifi in Olive. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Olive have air conditioning?
Absolutely! We offer over 20 cabin rentals with air conditioning in Olive. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Olive have free parking?
Absolutely! We offer over 20 cottage 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.

Vacation rentals in Olive

Top-rated vacation rentals in Olive

Vacation rentals for every style

Cottages

Houses

Cabins

Popular amenities for Olive vacation rentals

Stay near Olive's top sights

Other great vacation rentals in Olive

Home in Kingston

Home in Kerhonkson

Home in New Paltz

Cottage in Olivebridge

Cottage in West Shokan

Tiny home in New Paltz

Cottage in Kerhonkson

Apartment in High Falls

Quick stats about vacation rentals in Olive

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

How much does it cost to stay in cottage rentals in Olive?

Do cottage rentals in Olive have a kitchen?

What are the most popular amenities for Cottage Rentals in Olive?

Are there vacation rentals with a dedicated workspace in Olive?

Are there family-friendly vacation rentals in Olive?

Do cottage rentals in Olive have wifi?

Do cabin rentals in Olive have air conditioning?

Do cottage rentals in Olive have free parking?

Are there Olive vacation rentals on Airbnb with pools?

Are there pet-friendly vacation rentals in Olive?

Destinations to explore