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Vacation rentals in Olive

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Top-rated vacation rentals in Olive

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

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Cottage in West Shokan

4.95 out of 5 average rating, 155 reviews

Cozy Catskills Getaway w/AC on 3 Acres—Updated ‘24

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.

Guesthouse in Accord

4.94 out of 5 average rating, 138 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.

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 323 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.

Guesthouse in Olivebridge

4.94 out of 5 average rating, 116 reviews

The Ashokan Guest House

This newly renovated guest house is attached to a 120 year-old former Boarding House which housed the workers building the Ashokan Reservoir. This quiet refuge sits on a lovely 3-acre lot in Catskill Park within .5 mile of Ashokan Reservoir. An outdoor adventure in our beautiful Catskill Mountains awaits any direction you go. This is the perfect location for couples or individuals looking for a retreat (it is not child-proofed/child friendly!). Near Kingston, Woodstock and Stone Ridge.

Cabin in Kerhonkson

4.92 out of 5 average rating, 429 reviews

Home Alone Woods

Small and charming cabin in a quiet place surrounded by woods and nature with the hiking trails half a mile away. There is an easy access to Hunter Mountain, Minnewaska State Park, and Shawangunks. 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. WE DO NOT GUARANTEE THAT THE HOT TUB WILL BE AVAILABLE.

Cabin in Kerhonkson

5 out of 5 average rating, 345 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!!

Home in Kingston

4.96 out of 5 average rating, 286 reviews

Country Elegance with Beautiful Catskill Mt. Views

Great location, 20 minutes from Woodstock, Kingston, Stone Ridge, High Falls. 2 hours north of New York City. Located on a cul-de-sac with an incredible view of High Point Mt. with breathtaking sunsets minutes from the Ashokan Reservoir! We supply wood for the wood-burning stove + baseboard heat. We have Apple TV, Espresso coffee machine, French Press, Pour-Over, Blender, Magic Bullet, Food Processor and Toaster Oven. People from all backgrounds are welcome! Eco-friendly!

Guest suite in Woodstock

4.98 out of 5 average rating, 128 reviews

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

Cottage in Bearsville

4.99 out of 5 average rating, 163 reviews

Coldbrook Cottage

Welcome to Coldbrook Cottage. Less than 2 miles from The Onteora Mountain House wedding venue. A great romantic get-a-way. All 5-STAR reviews. We offer the amenities of a great hotel suite, but totally private. It's on one of Woodstock's nicest roads for walking, jogging, and bicycling. Wilson State Park is across the street and we're surrounded by protected land. 8 minutes to Woodstock. 20 minutes to Kingston. 20 minutes to skiing . Check our reviews!

Cottage in West Shokan

4.92 out of 5 average rating, 169 reviews

Relaxing Cottage in the Catskill Mountains

1000 sq ft. cottage located on a 7 acre partially wooded property in the Catskills. Two bedrooms (one queen, one full), one bath, open floor plan with vaulted ceilings and sliding glass doors opening to a deck in the back yard. Cook and eat on the deck with both gas and charcoal grills, plus large dining table with umbrella. Fire pit outside and wood burning stove inside for extra warmth and ambience. Dogs considered, just ask.

Guesthouse in Mount Tremper

4.92 out of 5 average rating, 347 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.

Cabin in Olivebridge

4.94 out of 5 average rating, 474 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

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Olive vacation rentals

Free parking on premises

Air conditioning

Stay near Olive's top sights

Ashokan Reservoir232 locals recommend

Bread Alone Bakery156 locals recommend

Boiceville Supermarket117 locals recommend

The Country Inn68 locals recommend

Kenneth L. Wilson Campground57 locals recommend

Ashokan Rail Trail- Boiceville Bridge Trailhead52 locals recommend

Other great vacation rentals in Olive

Home in Shokan

4.96 out of 5 average rating, 79 reviews

West Wing - a unique private space w/patio

Barn in Accord

4.95 out of 5 average rating, 542 reviews

Unique Barn Loft on Century Old Farm

Home in Boiceville

5 out of 5 average rating, 36 reviews

Cozy Secluded Streamside House

Home in Stone Ridge

4.96 out of 5 average rating, 134 reviews

Secluded Oasis w/ Screened Porch In Stone Ridge

Chalet in Olivebridge

4.99 out of 5 average rating, 143 reviews

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

Guesthouse in Olive

4.99 out of 5 average rating, 85 reviews

The Lily Cottage Guesthouse

Farm stay in Woodstock

4.84 out of 5 average rating, 236 reviews

Lenny Bee's Bee Happy AirBnB

Cottage in Boiceville

4.99 out of 5 average rating, 99 reviews

Magnolia Cottage

Quick stats about vacation rentals in Olive

Total rentals
200 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
16K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
30 properties have a pool

Frequently Asked Questions

How much does it cost to stay in guesthouse rentals in Olive?
Experience the best of Olive with our guesthouse rentals, starting at about $100 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 10 cottage rentals with a kitchen in Olive. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Olive?
Enhance your stay in our House Rentals with the most popular amenities: over 110 homes with free parking, over 110 homes with wifi, over 100 homes with a kitchen, over 90 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 140 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 110 house rentals with wifi in Olive. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Olive have air conditioning?
Absolutely! We offer over 10 cottage 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 110 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.

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