House holiday rentals in Olive

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Popular amenities for house rentals in Olive

House rentals with a pool

Superhost
Home in Woodstock
4.88 out of 5 average rating, 167 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 favourite
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 favourite
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 favourite
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
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 favourite
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 favourite
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 favourite
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

Top guest favourite
Home in Kingston
4.94 out of 5 average rating, 308 reviews

Hudson Valley Hygge House~ comfort in the country!

HallieRating, 5 stars3 months ago
My boyfriend and I were looking for a relaxing weekend escape from NYC and couldn’t have picked a better spot. We came to explore Kingston but loved the house so much that we were just as happy staying in, playing games, and soaking in the cozy vibes. The home is beautiful and thoughtfully appointed — I can only imagine how magical it must be in the summer with the porch, or in the fall with the foliage. Even in late winter, it was idyllic. The location is perfect — just about 10 minutes from Kingston, so it’s super easy to pop into town while still feeling tucked away. We’d absolutely stay here again!
Top guest favourite
Home in Woodstock
4.99 out of 5 average rating, 116 reviews

Idyllic Forest Home

JonRating, 5 stars1 week ago
What a wonderful, stylish home tucked away in the woods and with all the comforts of home. The indoor and outdoor spaces were both ideal for visiting, relaxing, and listening to music (what a sound system). It is perfectly situated close to Woodstock, Saugerties, Kingston, and numerous other attractions. Henry was a kind and responsive host, and always quick to respond to all of our questions. Highly recommended and a definite revisit next time we're heading upstate.
Top guest favourite
Home in Big Indian
4.98 out of 5 average rating, 108 reviews

Gingerbread House- a 1950s Catskills Chalet

RyanRating, 5 starstoday
Elizabeth’s cottage is the perfect home base to explore everything in the Catskills, especially many of the hiking trails. The Urban Cowboy Lodge is essentially next door and offers a great restaurant for dinner and drinks without having to travel into one of the nearby towns. The cottage is also really a unique space with an eclectic mid-century vibe. Definitely will stay here again.
Top guest favourite
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 favourite
Home in New Paltz
4.95 out of 5 average rating, 283 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

BlairRating, 5 stars1 week 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 favourite
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 favourite
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 favourite
Home in Halcott
4.98 out of 5 average rating, 105 reviews

Modern Mountain Retreat with Views on 18 Acres

AngelinaRating, 5 stars3 weeks ago
Another review said it was more beautiful than the pictures and I agree! The home and space was so serene even though it was a bit rainy. My partner and I felt safe and visited some food recommendations. We highly recommend mornings! And We hope to go back! Paul was truly an amazing and responsive host

Private house rentals

Top guest favourite
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 favourite
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!
Top guest favourite
Home in Kerhonkson
5 out of 5 average rating, 21 reviews

Kerhonkson Forest House

AnnieRating, 5 stars1 day ago
Inssaf’s airbnb in Kerhonkson was beautiful, clean, and just as described. Their home office setup was perfect for working remotely. There are many good restaurant and cafe options in the surrounding town, so we didn’t spend a whole lot of time cooking, but the kitchen had everything we needed to make breakfast in the morning before heading out for our day-time activities. Highly recommend!
Guest favourite
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 favourite
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 favourite
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 favourite
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 favourite
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

    ₹1,731 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

Destinations to explore

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