Vacation rentals in Portlandville

4.97 out of 5 average rating, 395 reviews

A cozy living area is displayed with warm wooden walls and a plush sofa adorned with vibrant pillows. A small green side table complements the space. A wood stove is positioned nearby, with a window allowing natural light to illuminate the area.

Cabin in Bovina Center

Delightful Cabin with Extras

SarahRating, 5 stars1 month ago

Had a lovely long weekend at Pamela & Alan's warm, cozy home. We made good use of the wood stove, grill, and hot tub and took advantage of the board game and DVD selections as well! We also enjoyed the local attractions such as the Putt Putt Van Winkle mini golf course, Brushland Eating House and Bovina Farm & Fermentory for delicious dinners, Wayside Cider, and even went for a little hike nearby. The house was clean and comfy and we felt right at home - thanks to Pamela and Alan for the wonderful stay!

4.95 out of 5 average rating, 94 reviews

An open living space features a high wooden ceiling with exposed beams and large windows that allow natural light to fill the room. A dining table with upholstered chairs sits in the foreground, while a cozy seating area with a stone fireplace and comfortable sofas is visible in the background.

Chalet in West Kill

Charming & Private Catskill Chalet

RachelRating, 5 stars2 months ago

We had a wonderful stay at Tony & Ines’s place! The hosts were very responsive and helpful. The house itself was cozy with plenty of space for our group of 5. The surrounding area was beautiful and super convenient to local ski mountains. Will hopefully stay again!

4.88 out of 5 average rating, 136 reviews

Catskills Retreat: Hot Tub | Fireplace | Firepit

LukeRating, 5 stars2 months ago

Absolutely amazing place and experience. Everything about the place was great and the communication and service was the best. We received 5 inches of snow on our last night and they even had the driveway all plowed for us first thing in the morning. That was a very pleasant surprise. Highly recommend!!

5 out of 5 average rating, 6 reviews

Chalet in Shandaken

Serenity Estate: Farmhouse+Cottage w Pool & HotTub

JesseRating, 5 stars3 months ago

Fouz & Chris were excellent hosts with an amazing property. From the time our booking was confirmed they were in contact with us to insure we had as comfortable a stay as possible. Check-in was simple and flexible. The house was great, clean and well equipped. Highly recommend.

4.96 out of 5 average rating, 157 reviews

A spacious living area features large windows, allowing natural light and views of the surrounding nature. Warm wooden walls and ceilings create a cozy ambiance. Various seating options include an armchair, a leather sofa, and a decorative table with four chairs nearby.

Cabin in Boiceville

Catskills Cabin Surrounded by Mountain Views+Spa!

LyleRating, 5 stars1 month ago

Loved the beautiful mountain views through the large windows or while enjoying the full sized deck. Three large bedrooms were great accommodations for our three couples. Very clean, very roomy and homey feel with lots of attention to the details that make for a smooth stay, Great kitchen facilities - meals were easy. Lots of “hanging out “ space perfect for spending relaxing time together. Loved playing the old vinyl records and board games. Key cabin location enables rapid access to so many activities and sites to see. So happy we chose the Fratt Lodge. We cant wait to come back!

Cottage in Livingston Manor

4.99 out of 5 average rating, 146 reviews

Cozy mountain top home - views, 5acres & a gym.

NikhilRating, 5 stars2 weeks ago

The cottage was lovely and very comfortable. Simon left us detailed instructions and we had no issues in finding it and settling in. As the weather took a turn for the worse, we spent most of a day cozy in the house. Our dogs were also very comfortable and loved the large backyard. The house decor is very tastefully done, and not only looks great but looks like special effort has been taken to make everything comfortable and easy to use. Thank you for sharing your home!!

5 out of 5 average rating, 18 reviews

A tranquil landscape view of a gently flowing stream bordered by greenery. The spacious backyard features well-kept grass and natural stones. The modern home is visible in the background, showcasing a large deck that overlooks the serene setting.

Home in Franklin

All Star Village Modern Waterfront Luxury Home

DebraRating, 5 stars4 months ago

Easily accomodated our large group with 3 bedrooms, 3 bathrooms and the large living room/dining room space for us to gather. Plenty of kitchen equipment for us to prepare meals and loved the extra sink and bar area for food prep. The fake fireplace was great with the temperatures outside below freezing. Lovely back wooded area with the brook to see from the back porch. Hosts were quick to respond and their home was beautiful.

Superhost

A serene riverfront view showcases a calm waterway framed by lush greenery. A large rock outcrop emerges from the water's edge, while a deck with red umbrellas is visible above, offering a peaceful retreat surrounded by nature.

Home in Middletown

4.9 out of 5 average rating, 130 reviews

Riverfront! Swim, Fish, Hot Tub & Game Barn.

SamanthaRating, 5 stars1 week ago

Beautiful home in a very private area. Lots of family games and lots of outside things todo. Me and my family had a wonderful Easter weekend get away. Only complaint I would have is the jacuzzi smelled weird and stuff was coming out of the jets but other than that it was perfect! We all were very comfortable and had a blast with the kids.

4.99 out of 5 average rating, 121 reviews

A view from the covered deck showcases rolling hills and lush greenery. The well-maintained lawn leads into a natural landscape with trees and shrubs, creating a serene atmosphere. Overcast skies complement the vibrant shades of green, enhancing the tranquil setting.

Cottage in Milford

At Home Base Yellow Cottage

SusanRating, 5 stars1 week ago

We were very satisfied with the house, good location, clean, great host, beautiful surroundings, good for pets, had everything we needed! Be aware that there are 3 houses on the property so you are sharing the very large yard which can be good for teams and families but you may not want. We were lucky to have a nice family across from us. Highly recommend!

4.95 out of 5 average rating, 397 reviews

Home in Cooperstown

Cooperstown Hall of Fame, Dreams Park Baseball

Mary Ann And JeffRating, 5 stars3 days ago

Dave's property was the perfect choice for our overnight trip to Cooperstown with another couple. Located on a quiet country road, it's only a couple of miles to the Hall of Fame in one direction and Ommegang Brewery in the other. The house was spotless and very comfortable, and has been totally updated with everything one needs. Highly recommend!

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Popular amenities for Portlandville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Portlandville

A spacious great room is highlighted by vaulted ceilings and a stone fireplace. Oversized windows allow natural light to fill the space, with mountain views visible outside. A large flat-screen TV is mounted above the fireplace. Comfortable seating is arranged for relaxation.

5 out of 5 average rating, 11 reviews

Mayfair Manor Mountain Retreat

MollyRating, 5 stars2 months ago

Great stay, wonderfully responsive host. We needed ice taken care of in the driveway and the host was very responsive And proactively responded to our needs.

4.85 out of 5 average rating, 39 reviews

An open living area features a stone fireplace as the focal point, surrounded by large windows offering views of the outdoors. Comfortable seating is provided by a blue couch and armchairs, while a patterned rug adds a touch of warmth to the wooden floor.

Home in Roxbury

Spacious Catskills Ski House

AshleyRating, 5 stars1 month ago

Anna’s mountain house was the perfect weekend getaway. A group of 10 of us stayed very comfortably as a gathering of both adults and kids. The house was cozy with plenty of living and gathering spaces. Some of the highlights for us was going on nature walks on the beautiful property featuring a pond and a babbling brook that we could walk over on a boardwalk, the simple on/off gas fireplace made for wonderful heat and ambiance, well appointed kitchen was conducive to large group meals, and the furnishings throughout the house were so functional and so stylish. Anna herself couldn’t have been kinder or more helpful and responsive- going above and beyond to ensure our multi family weekend getaway went off without a hitch. We all agreed we will absolutely be returning. This location would be great during any season and we can’t wait to experience it during other times of the year as well. Thanks again Anna!

An aerial view shows a large wooden home surrounded by lush trees. A well-maintained pathway leads to the entrance, with shrubs and rocks lining the yard. A fire pit area is visible in the front, offering a cozy outdoor space.

4.99 out of 5 average rating, 106 reviews

“Spectacular Mountain Views with Tranquility”

DanielleRating, 5 stars2 months ago

Beautiful home! Very convenient to Windham mountain/town. We would definitely stay again

4.8 out of 5 average rating, 60 reviews

A hot tub is shown, equipped with multiple jets and surrounded by a wooden railing. Lush green hills are visible in the background under a clear sky, providing a serene setting for relaxation.

Home in Margaretville

Escape to Serenity: 18-Acre Catskill Retreat

JesseRating, 5 stars1 month ago

Great host and place all around! Kim was very responsive before, during, and after the trip. The amenities were great and location was close by Plattekill. She recommended ahead of time to bring an AWD vehicle as her driveway is on an incline. I’d recommend this stay.

4.95 out of 5 average rating, 39 reviews

Steps from the slopes 3 bedroom w/loft End unit

RaelynnRating, 5 stars2 months ago

Catherine’s place was great for our visit! Super close for Windham skiing although if you’re carrying all your gear and have kids you’re better off driving. Pool building was right out the back door but unfortunately the hot tub was broken so we didn’t bother going over. Had a few questions during our stay and Catherine was very quick to respond. The house was cozy and comfortable. Upstairs can get pretty warm and the air is pretty dry but after a day of skiing, we were out cold in the comfy king bed. If you’re visiting during the week, have some back up plans for restaurants and meals since a lot of places were closed (even when they were supposed to be open). Not a reflection of our stay at Catherine’s but it may be helpful to know! Would definitely rent this place again should we visit Windham.

Home in Hunter Mountain, Hunter

A hammock hangs between two trees on a grassy area, inviting relaxation. The multi-level home features a wooden deck above, surrounded by lush greenery and trees. The exterior walls are a mix of wood and white, blending harmoniously with the natural setting.

4.96 out of 5 average rating, 104 reviews

Private Mountain Lodge, 10mins to Hunter & Windham

PaulRating, 5 stars2 months ago

My family's second visit to this beautiful gem overlooking the mountains and frozen pond. Our hosts are highly communicative and helpful. The description is accurate. Considering our 2nd visit and rebooked for 3rd in 2026 - this speaks volumes -- more than meets our needs, well stocked. We're looking forward to visiting during the summer months to further appreciate the views. Grateful to them for sharing their home with us.

4.95 out of 5 average rating, 136 reviews

A circular seating arrangement is surrounded by six wooden chairs around a fire pit, set on a gravel surface. Soft string lights are overhead, illuminating the area. A grill is positioned nearby on the grass, with stacked firewood visible in the background.

Home in Hunter

Modern House with Mountain View @Getawind

JenniferRating, 5 stars2 weeks ago

A very beautiful home. Stayed here for a couple of days in April and it was the most peaceful getaway. It is ideal if you just need some rest and relaxation. Loved the sauna and the hot tub.