Pet-friendly vacation rentals in Olive

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Olive

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 640 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 19 – 26

€ 134 per night

Guest favorite

Cabin in Boiceville

4.95 out of 5 average rating, 126 reviews

Catskills Cabin Surrounded by Mountain Views+Spa!

Location is Everything! Our 3BR Catskills home is surrounded by breathtaking mountain views, and close to everything including Woodstock Village, Phoenicia, Rivers, Hikes, Breweries, Ski Areas and more. Home is set high on a ridge overlooking nature from all angles on 3 private acres of land, a perfect location for exploration. Interior tastefully decorated with brand new beds and furniture, fully stocked kitchen. Enormous deck facing mountains with fire pit, grills. Town of Olive STR-22-12.

Sep 17 – 24

€ 545 per night

Guest favorite

Guest suite in Kerhonkson

4.95 out of 5 average rating, 128 reviews

Private Apt. in Vintage House steps to Kerhonkson.

Private sunlit upstairs apt. features magical views of The Catskills. Pets are welcome ($25 fee). One room is a master bedroom with a workspace, TV and huge closets. Second room has a full kitchen (gas stove, fridge/ freezer, sink) large table, sofa that folds out to a full size bed. Use of fire pit, back yard, cafe size tables, outside chairs for your convenience. Unlimited free access to Minnewaska State Park, (save $10 fee). The house is walking distance to town and the Rail Trail. Welcome!

Oct 17 – 24

€ 75 per night

Guest favorite

Home in Olivebridge

5.0 out of 5 average rating, 101 reviews

Olive Outpost: Catskills 3BR House on Private Road

Welcome to the Olive Outpost in The Catskills! (@oliveoutpost) Our light-filled, 1,600 SF, 3-bed, 2-bath house is on 32 acres off a private road and ideal for a small group (6 or under). We're close to the towns of High Falls, Stone Ridge & Accord (15 mins), Woodstock, Phoenicia (25 mins) & Kingston (30 mins). NOTE: There is a guest cabin on the property where the owners may be staying (or available for additional capacity) Photos courtesy of @nicoschinco Town of Olive STR Reg #: STR-22-6

Jun 5 – 12

€ 433 per night

Guest favorite

Cabin in Kerhonkson

4.98 out of 5 average rating, 121 reviews

Lovely Catskill Cabin w/Piano and free firewood

When you truly want to get away from it all, come experience the wilderness of the Catskills. We're nestled next to 30k acres of the Sundown Wild Forest inside the 300k acres Catskill Park, 2 hrs from NYC. Enjoy any of the 3 fireplaces located in and around the cabin after your choice of 8 hiking trails you can take from our doorstep including the cascading pools of the secluded Vernooy Kill Falls. We are the closest Airbnb to the historic Vernooy Kills Falls and its 300-year-old ruins.

Dec 25 – Jan 1

€ 197 per night

Guest favorite

Cottage in Olivebridge

4.91 out of 5 average rating, 116 reviews

Highpoint House: historic farmhouse on four acres

Built in 1790 and fully renovated in 2015, this historic farmhouse is set on four private acres at the foothills of the Catskills. Enjoy the serenity of the extensive lawns, explore the woods that lead up to High Point mountain, or venture out to experience all that the region has to offer. Highpoint House is within a half-hour drive of Kingston, Woodstock, Phoenicia, and just two hours from NYC, making this the perfect, secluded, four season retreat. Registration No: STR-23-16

Feb 2 – 9

€ 299 per night

Guest favorite

Home in West Shokan

4.92 out of 5 average rating, 333 reviews

1850 Carriage House, Creek

Sunny Carriage House near the Ashokan Rail Trail and Catskill high peaks, with the beautiful sound of the nearby Bushkill Creek. Spacious, clean, peaceful. Fast reliable WIFI, woodstove. Two bedrooms, marble bathroom, AC, fire pit. A comfortable mix of handmade wooden mid-century minimalism. The house is in a beautiful natural setting while a short drive to town, restaurants. If The Carriage House is booked for your dates, check out Watson House, a 150-year-old house next door.

Jun 6 – 13

€ 298 per night

Guest favorite

Cottage in Kerhonkson

4.91 out of 5 average rating, 378 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.

Jul 23 – 30

€ 157 per night

Guest favorite

Home in Mount Tremper

4.96 out of 5 average rating, 214 reviews

Overlook Creek Cottage 1 Near Phoenicia

Located on the Esopus, Overlook Creek Cottage is a newly renovated space including modern kitchen and bathroom amenities, mid century modern design with a Bohemian flair and proximity to destinations such as the town of Phoenicia, The Pines restaurant, Phoenicia Diner, Foxfire Mountain House, The Emerson Resort and Mt. Tremper Arts. Nearby to hiking trails and other towns such as Woodstock and Kingston as well as the Ashokan Reservoir.

Dec 28 – Jan 4

€ 167 per night

Guest favorite

Cottage in West Shokan

4.91 out of 5 average rating, 160 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.

Jul 24 – 31

€ 316 per night

Guest favorite

Cabin in Olivebridge

4.93 out of 5 average rating, 428 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

Oct 28 – Nov 4

€ 182 per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 678 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

Feb 28 – Mar 7

€ 129 per night