House vacation rentals in Olive

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Popular amenities for Olive house rentals

House rentals with a pool

Superhost
An above-ground pool is surrounded by a wooden deck featuring lounge chairs. Lush greenery and trees provide a natural backdrop, while a fenced area with a swing set is visible in the distance, creating a serene outdoor space for relaxation.
Home in Woodstock
4.89 out of 5 average rating, 166 reviews

Shula | Farmhouse | Pool, Fire pit, Hot tub

MimiRating, 5 stars3 weeks ago
Cute house, open concept first floor was great for a weekend with our girlfriends! Hava was very responsive and kind!
Guest favorite
A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.
Home in Stormville
4.94 out of 5 average rating, 182 reviews

Private Hudson Valley Country Retreat

JackieRating, 5 stars2 weeks ago
This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!
Guest favorite
A private saltwater pool is surrounded by lush greenery, featuring a smooth stone deck. The clear blue water invites relaxation, while steps lead into the pool. Trees provide natural shade along the perimeter, creating a serene outdoor setting.
Home in Woodstock
4.87 out of 5 average rating, 135 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

KimberlyRating, 5 stars2 weeks ago
Our stay at Susanna’s was perfect! We have zero complaints. Had everything we needed and more! We would definitely stay there again when in the area!
Guest favorite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck
4.89 out of 5 average rating, 144 reviews

4Br Mountain Brook House on 130 acres w/ trails

AnnetteRating, 5 stars3 weeks ago
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.
Superhost
An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.
Home in New Paltz
4.86 out of 5 average rating, 159 reviews

Scenic River View Escape | New Paltz

TatiaRating, 5 stars3 weeks ago
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!
Guest favorite
A serene heated saltwater pool is framed by lush greenery, reflecting the sky above. A rustic wooden edge provides a natural transition between the pool and the surrounding landscape, which includes a prominent tree adding to the tranquil ambiance.
Home in Woodstock
4.92 out of 5 average rating, 245 reviews

Little owl Japanese teahouse: pool is OPEN

MaryRating, 5 stars3 days ago
The teahouse and surroundings were relaxing and peaceful. We saw groundhogs, deer, and chipmunks from the porch and our 2 dogs loved exploring the field and wandering in the nearby woods. The pool was amazing and warm despite the rain and the natural landscaping couldn’t have been more beautiful. We really enjoyed our stay!
Guest favorite
Home in New Paltz
4.93 out of 5 average rating, 135 reviews

Harrison Field Pool Bike2Town FirePit 10AcreViews

EmmaRating, 5 stars3 weeks ago
We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!
Guest favorite
A welcoming front patio is shown with two chairs positioned near the house. Surrounding lush green grass extends to the horizon, featuring a backdrop of gentle hills and a few distant buildings, including a red barn, under a clear blue sky.
Home in Narrowsburg
4.95 out of 5 average rating, 202 reviews

Modern House with Private Pool, Hot-Tub, Fireplace

AlexandraRating, 5 stars3 weeks ago
It was a beautiful stay and everything were just like the photos! We enjoyed our stayed!

Weekly house rentals

Guest favorite
A spacious main room features barn-like vaulted ceilings with exposed beams and polished concrete floors. Modern kitchen appliances and cabinetry are complemented by a large L-shaped sofa adorned with pillows. A ping pong table is present, and large windows provide views of the surrounding forest.
Home in New Paltz
4.95 out of 5 average rating, 147 reviews

New Paltz Guest Cabin Nestled In The Woods

PhilRating, 5 stars1 week ago
Beautiful location, peaceful and private. Spacious, modern, comfortable home. Really good advice about places to explore and visit in the surrounding area. This is a place we’d return to in a heartbeat. Just the tonic after a week in Paris and a hectic entry via JFK. Ben’s place is a haven away from the world. We just loved it!
Top guest favorite
A spacious bedroom features a queen size bed with soft bedding and a cozy area rug. Large windows provide natural light and views of the surrounding forest. Wooden beams and warm wooden flooring contribute to a serene atmosphere.
Home in Accord
4.97 out of 5 average rating, 137 reviews

The Woods House, 40 secluded acres & speedy wifi!

DanRating, 5 stars4 weeks ago
Donna's place was amazing! We knew we would love it from the pictures but were even more blown away when we walked inside. It was the perfect cabin with every amenity and more that you could want for a remote get away in the Catskills. We went up with our dog and loved every minute - will definitely go back for our next trip up!
Top guest favorite
A charming Swiss chalet is nestled among tall trees, surrounded by lush greenery. The house features a welcoming deck and multiple windows that provide natural light. A stone path leads to the entrance, inviting guests to explore the tranquil outdoor setting.
Home in Big Indian
4.98 out of 5 average rating, 107 reviews

Gingerbread House- a 1950s Catskills Chalet

AichaRating, 5 stars2 weeks ago
Overall a great stay! The home was beautiful and exactly what we needed. Elizabeth was also a great host. We’d be more than glad to visit again in the future!
Top guest favorite
The exterior of the mid-century modern cottage is displayed, featuring a light-colored facade with a prominent red door. Lush greenery surrounds the property, and a well-maintained lawn is visible, offering a serene ambiance against the backdrop of trees.
Home in Olivebridge
4.96 out of 5 average rating, 24 reviews

Olive Star Cottage & Garden

EmilyRating, 5 stars2 months ago
The cottage was modern and clean and provided all the necessities of home. The beds were very comfortable, the kitchen had all the basic staples, and the dining table had a perfect view of the backyard and surrounding wildlife (deer every morning). The location of the cottage is close enough to Woodstock village and Ashoken reservoir for daily activities.
Guest favorite
The living room features large windows offering views of the river and surrounding trees. A blue sofa and a beige tufted couch are positioned around a wooden coffee table, while a colorful area rug adds warmth to the space. Bright yellow walls enhance the inviting atmosphere.
Home in New Paltz
4.95 out of 5 average rating, 283 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

BlairRating, 5 stars6 days ago
A very lovely place to stay! The description matched the place exactly. We enjoyed spending a lot of time outside on the deck bird watching and even saw some fish jumping in the river. The property is also very private which was a huge plus -- no visible neighbors in any direction while spending time outside. Seth was a very responsive host and did a great job with the design of the house. There were lots of thoughtful touches that made the stay extra nice. Would love to stay again!
Guest favorite
A fire pit made of stacked logs is in the foreground, with bright flames dancing above. In the background, a serene lake is flanked by lush trees, reflecting the surrounding mountains bathed in early morning light.
Home in Chichester
4.97 out of 5 average rating, 153 reviews

Stunning Pvte Lakehouse•Swim•Hike•Mntn Views•F/pit

SusanRating, 5 stars3 weeks ago
Excellent location with private pond. This home was truly built for a family gathering. Wonderful entertaining spaces, large fireplace with an expansive kitchen to cook in. There is a large game room with board games to suite all ages, billiards, croquet, and a small row boat for fun.
Guest favorite
A spacious living and sleeping area is shown, featuring a white bed with a wooden base and two side tables. Natural light enters through nearby windows, illuminating a cozy nook that is partially visible. A comfortable seating area is also present, enhancing the room's open feel.
Home in Kerhonkson
5 out of 5 average rating, 54 reviews

Modern Cabin on 7 Acres in Catskill forest w/ Pond

GretchenRating, 5 stars2 weeks ago
Great place to stay in the Catskills if you want something peaceful in the woods. It was a great price for how clean, quiet and aesthetically pleasing this place was. While it was off the beaten path, it was a short drive to many of the cool places in the area and the hosts give a great book of recommendations that was very helpful. Would stay here again!
Top guest favorite
A modern house is seen, constructed with a combination of stone and wood materials. Large picture windows are positioned throughout, allowing natural light to flow in. A landscaped rocky path leads to the entrance, surrounded by greenery and trees.
Home in Rhinebeck
5 out of 5 average rating, 214 reviews

Eagle Rock House

DavidRating, 5 starstoday
We were 2 couples staying for 3 days in June with a bit of a heatwave but AC was great. Rooms are big and not cluttered. Great master bedroom and master bathroom. Kitchen had everything we needed, got nice bread from Rhinebeck in the morning.

Private house rentals

Top guest favorite
An outdoor fire pit is surrounded by wooden chairs, creating a cozy atmosphere for gatherings. The setting sun casts a warm glow over the home, visible in the background, with trees framing the scene and outdoor lighting enhancing the tranquil ambiance.
Home in Olivebridge
5 out of 5 average rating, 80 reviews

Olive Woods House - Catskills Mountain Views

LindsayRating, 5 stars3 weeks ago
One of my best Air BnB stays ever: beautiful house, great amenities and a wonderful location. Already planning our next trip back!
Guest favorite
Home in Olive
4.94 out of 5 average rating, 31 reviews

Perch Eagle House: Creek access + Sauna + Mt views

JoshRating, 5 stars1 week ago
Had a great time again in Olive. Nice little house close to the river. Would definitely come back again!
Guest favorite
A two-story home is surrounded by lush greenery and trees, featuring a spacious front porch with a railing. The home’s light-colored exterior contrasts with the vibrant outdoor setting, providing a serene atmosphere. A well-maintained lawn leads to a natural area in the background.
Home in Olivebridge
4.98 out of 5 average rating, 63 reviews

Country Getaway with Mountain View

CatherineRating, 5 stars2 months ago
This was the perfect vacation house in the woods for our family. My two young children loved all of the toys available. I quickly realized I did not have to even open the bag of books and toys we brought with us because there was more than enough here! Being in the middle of the woods was exactly what we were looking for. The house was well stocked with towels and all necessary cooking supplies. I would suggest a couple of extra blankets for cooler weather, as the bedroom downstairs was quite cold when we arrived. Otherwise, we had an excellent stay and we would definitely come back.
Top guest favorite
A vintage earthmoving machine is positioned on a gravel lot, showcasing rusted metal and worn paint. A hydraulic crane and digging bucket are visible, surrounded by lush green trees in the background. The sky features a mix of clouds with patches of blue.
Home in Olivebridge
5 out of 5 average rating, 9 reviews

The Earthmover Inn

SukiRating, 5 stars5 months ago
Staying at the Earthmover Inn was the best decision we made this holiday! The house was impeccably clean and cozy, and Roger and Ruth left lots of great treats, like small chocolates and coffee and tea. We had a blast playing Scrabble by the fire, and the whole stay was wonderful. Roger and Ruth are attentive and kind communicators, and you can tell they care a lot about the comfort of the folks staying here. The BNB is within 10 minutes of Stone Ridge, and only a few minutes away from Tetta's and the Country Inn, for closer options for groceries and food. I grew up in the neighborhood, and staying here while visiting family for the holidays made me feel right at home!
Top guest favorite
A mid-century cabin emerges amidst a snowy landscape, showcasing a stone and wood exterior. A snow-covered deck extends from the upper level. Surrounding trees are dusted with snow, and a soft blanket of white covers the ground, creating a serene winter setting.
Home in Denning
5 out of 5 average rating, 36 reviews

Midcentury House in the Catskills

AviRating, 5 stars2 months ago
Had a wonderful trip at this cabin. The space is cozy, thoughtfully decorated, and surrounded by nature — exactly what we were hoping for. The well-stocked kitchen made cooking a joy, and we especially loved using the outdoor pizza oven. The fireplaces and wood stove added to the warm, inviting vibe throughout the home. The property itself is stunning —the a creek and a pond were fun to explore. We even got to see tadpoles hatching in the pond! It felt like a true escape. Zachary was a fantastic host — super communicative and helpful from start to finish, which made everything easy and stress-free. Would highly recommend staying here!
Top guest favorite
A spacious kitchen island is adorned with a vase of fresh yellow flowers, providing a cheerful focal point. In the background, a stone fireplace features a large artwork of a bear, and large windows allow natural light to fill the inviting dining area.
Home in Stone Ridge
4.97 out of 5 average rating, 33 reviews

Stone Ridge Farmhouse, w/ hot tub

RichardRating, 5 stars2 days ago
We had a wonderful stay at the farmhouse in Stone Ridge. The house is comfortable and the kitchen is nicely appointed making cooking enjoyable. The property is quiet and private but close to Stone Ridge. Holly was quick to welcome us and provide all the info needed to settle in. We highly recommend the farmhouse in Stone Ridge if you are looking for privacy and relaxation.
Guest favorite
A comfortable living room features a leather sofa in warm tones, set against a backdrop of natural light from the windows. A working fireplace with decorative accents and a large TV on a modern red console add functionality. Decorative plants and art pieces provide subtle color.
Home in Kerhonkson
4.95 out of 5 average rating, 43 reviews

Hudson Valley home with covered porch, fireplace

VilenaRating, 5 stars6 months ago
Great house/cabin for a nature getaway. Exactly as described, and I appreciated very clear instructions about everything. Loved attention to details and high-quality touches throughout the house and cute retro vibes. Very comfy beds and linens. We stayed over the Thanksgiving weekend, and were able to cook a holiday dinner for ourselves as the kitchen is fully equipped. The heating worked well considering freezing temperatures, but it makes some blowing noise, in case you are sensitive. I imagine that in warm weather this house sould be an absolute gem.
Guest favorite
The image showcases a charming wooden house nestled in a wooded area, surrounded by greenery. Warm lights glow from the windows, highlighting the home’s inviting exterior. Below, a serene creek winds through a forest, with sunlight filtering through the trees, reflecting off the water.
Home in Olivebridge
4.98 out of 5 average rating, 50 reviews

Catskills Haven With Private Creek

SarahRating, 5 stars1 month ago
The house was clean and comfortable. We didn’t have any issues

Quick stats about house rentals in Olive

  • Total rentals

    100 properties

  • Nightly prices starting at

    ﺩ.ﺇ73 before taxes and fees

  • Total number of reviews

    6K reviews

  • Family-friendly rentals

    90 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    20 properties have a pool

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