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Condo vacation rentals in Middletown

Find and book unique condos on Airbnb

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Popular amenities for Middletown condo rentals

Weekly condo rentals

Guest favorite
The entrance features a white door with small square windows at the top, adorned with a decorative planter holding greenery. The door is framed by a contrasting orange wall, providing a welcoming appearance.
Condo in Hunter
4.87 out of 5 average rating, 87 reviews

Cozy Gem with Mountain Views

AbishekRating, 5 stars3 weeks ago
Loved this place. Very easy to find. The place is cute and co portable with good views from the main bedroom and living room. Very clean and tidy. Loved the stay.
Guest favorite
Condo in Hunter
4.96 out of 5 average rating, 23 reviews

Mountainside Haven

AndreaRating, 5 stars1 month ago
The location was very peaceful and comfortable. It has a great view of the mountains in the background. The place had everything you needed and was very clean and had cabin like qualities. Very beautiful inside and outside as well. The host was very kind and responded right away to any questions I had.
Guest favorite
A patio area features a small circular table accompanied by a single chair, surrounded by lush green grasses and shrubs. In the background, a hillside with trees and a mountain is visible under a partly cloudy sky.
Condo in Vernon Township
4.96 out of 5 average rating, 52 reviews

Deluxe 1 Bdr | Walkout Patio to Pool & Hot Tub! | Mountain Creek Resort @ Appalachian

BrianRating, 5 stars1 month ago
This is a great condo if you visit Mountain creek. The furnishings are very nice, great feel to the unit. Location wise it can’t be beat. It’s right near the pool, great patio and easy walks to the lift for mountain biking. Even being close to all that it is still quiet and relaxing. The unit was very clean, bathroom is great size and the hosts provided everything g you could want. Definitely would stay here again.
Guest favorite
Condo in Vernon
4.97 out of 5 average rating, 58 reviews

New Luxury Ski Condo-2 Full Bathrooms

SavannaRating, 5 stars4 days ago
Great place to stay ! Host was responsive and had great local recommendations ! We really enjoyed our stay and will be definitely be back !
Top guest favorite
A well-lit laundry area features a full-size washer and dryer, complemented by white shelving for storage. The neutral-colored walls contribute to the clean and functional design, providing a practical space for laundry tasks.
Condo in Downtown Stamford
4.98 out of 5 average rating, 42 reviews

Downtown Living w/ parking, W/D & Wi-Fi+!

RajkumarRating, 5 stars1 week ago
Very nice location, quiet, yet central . House was well stocked and Aaron was prompt with communication. I had to modify my itinerary and Aaron was very accommodating.
Guest favorite
Condo in Vernon Township
4.93 out of 5 average rating, 69 reviews

Comfortable, chic, modern and sophisticated condo

MicheleRating, 5 stars3 weeks ago
First time in the area, and it was quite pretty! We were only there 2 nights and for our grandson's christening so we didn't spend a great deal of time at the resort, but it looked very popular (2 weddings and a slew of mountain bikers)! The condo was very comfortable and even nicer than the pics. Janet had great instructions for checking in and everything was very clean. We would stay again!
Guest favorite
An outdoor patio is set up for dining, featuring a wooden table with plates, glasses, and a vase of flowers. Nearby, white chairs provide additional seating. In the background, a serene pond reflects the clear blue sky and surrounding greenery, illuminated by the sun.
Condo in Hunter
4.82 out of 5 average rating, 65 reviews

Perfect Catskills hiking getaway with fireplace

AlexaRating, 5 stars3 weeks ago
5 stars, 5 stars, 5 stars!! I would just like to say I’ve stayed in many Air B&Bs before, and this one is by far one of my favorites. The hosts are absolutely amazing. They are proactive in responding and really want you be be comfortable and making sure you have no issues. The price was 100% worth it. I love that they included board games as a part of the space, such a nice touch. The bathrooms and bedrooms were also so clean, and we enjoyed our stay. You can really tell the hosts put a lot of love and care into this place. I can’t say enough good things about them!
Top guest favorite
A hallway features dark wooden paneling and intricate moldings, creating a classic architectural look. A patterned carpet runs along the floor, leading to several closed doors, while decorative lighting adds a subtle touch of brightness.
Condo in Harlem
5 out of 5 average rating, 36 reviews

Artful 3BDR: Near Subway, Stadium + Private Patio

KarenRating, 5 stars2 days ago
Great place in a great neighborhood. Easy access to subway. Host lovely to communicate with and fabulous getting to check-out with a to-do list.

Pet-friendly condo rentals

Superhost
A hillside is dotted with multi-level units, each featuring balconies, set against the backdrop of lush trees. A golf cart travels along a well-maintained fairway in the foreground, with expansive green grass stretching across the landscape.
Condo in East Stroudsburg
4.67 out of 5 average rating, 15 reviews

Shawnee Village 2 bedroom Sleeps 6

ElonRating, 5 stars40 months ago
Tawny was a great host. She communicated with me throughout my stay to make sure things went smoothly. Her hospitality is 10/10 and would recommend booking with.
Guest favorite
A inviting living area showcases a stone fireplace and wooden furniture. A rectangular dining table with chairs occupies the space, complemented by a comfortable seating arrangement. Natural light filters through large windows, highlighting a patterned area rug that adds warmth to the room.
Condo in Hunter
4.93 out of 5 average rating, 15 reviews

Condo on Hunter Mt.

AkankshaRating, 5 stars7 months ago
The house was beautiful. My friends and i had a great stay. The hang out place on third floor was best. The rooms were cozy and the porch was the best part. Would definitely recommend.
Top guest favorite
Condo in Kerhonkson
5 out of 5 average rating, 24 reviews

Bright & Cozy | Walk to Rail Trail

FangRating, 5 stars3 weeks ago
Well designed, well maintained modern style home. Love the warm toned interior. Quick drive to lots of hiking spots which was what brought us here. Management team was very professional and easy to communicate. Will consider for any future trips to Minnewaska/Mohonk.
A welcoming entrance sign for Black Creek is positioned alongside a tree-lined road. Lush greenery and flowering plants are arranged around the sign, enhancing the natural landscape. The area is well-maintained, providing an inviting atmosphere for visitors.
Condo in Vernon Township
4.82 out of 5 average rating, 101 reviews

Cozy Summer Escape - MTN Creek

StephenRating, 5 stars1 month ago
Great host. great place. a great getaway and very relaxing. would definitely stay again. great location! beautiful surroundings!
Top guest favorite
A spacious living and dining area is highlighted by a large wooden dining table surrounded by light-colored chairs. A comfortable seating arrangement is positioned nearby, facing a wall-mounted TV. Natural light enters through large windows, and a spiral staircase leads to the loft area.
Condo in Vernon Township
5 out of 5 average rating, 64 reviews

Chic-Retro Ski Loft | Mountain Creek slope-side

AlexisRating, 5 stars3 weeks ago
Peaceful weekend away from the city. We had a great time doing some hiking, visiting farms and enjoying the fresh air. I could see us visiting again.
Superhost
A well-lit bedroom features a spacious bed with white linens and an accent pillow. Bright light streams in through two windows adorned with sheer curtains. A side table with a small lamp adds a touch of warmth to the inviting space.
Condo in Kingston
4.91 out of 5 average rating, 144 reviews

Cozy & walking distance to cafés *spring avails*

JananiRating, 5 stars2 months ago
Cozy apartment, walking distance from the water front. Had a great weekend getaway.
Top guest favorite
An outdoor seating area features a cozy loveseat and chair, adorned with vibrant cushions in lemon and geometric patterns. A small glass table sits in front, inviting relaxation while overlooking lush green trees and a serene landscape.
Condo in Vernon Township
4.98 out of 5 average rating, 97 reviews

Chic Vernon Getaway | Pet-Friendly with Mtn Views

AmandaRating, 5 stars1 week ago
A perfect spot to stay for this location! The space is inviting and immerses you in nature with the window covered living space. We would definitely recommend!
Guest favorite
The exterior of the condo is showcased, featuring a two-story structure with a combination of red siding and stone accents. Balconies with wooden railings extend from the upper levels, and a prominent stone chimney rises against a cloudy sky.
Condo in Hunter
4.95 out of 5 average rating, 61 reviews

Hunter Mountain 2BR Condo - Steps to Slopes!

KellyRating, 5 stars3 months ago
This is my second stay at Daniel’s, and it was just as good as the first! I love the location of his place in relation to the mountain. It’s a quick walk up the parking lot to the trails/lifts. Most importantly, my pups feel right at home, and they know his place now! His home is always clean and the linens/towels always smell fresh! I told him I will be coming back multiple times throughout the snow season to go boarding. He is very responsive and helpful and would go out of his way if need be! Overall, 12/10 recommend Daniel’s spot!

Condo rentals with a pool

A cluster of multi-story wooden buildings is nestled among trees displaying autumn foliage. Each unit features large windows and balconies, with steps leading up to the entrances. The setting includes a grassy area and parked vehicles in the foreground.
Condo in East Stroudsburg
4.6 out of 5 average rating, 45 reviews

Wyndham Shawnee Village | 2BR/2BA Balc Queen Suite

BethRating, 5 stars8 months ago
Making arrangements with David was super easy. The place was really comfortable and had everything we need. It’s a timeshare so you don’t know what unit you’ll get. The one we were in was quite outdated but we weren’t there for the esthetics and it was clean , comfortable, and very convenient. There are lots of things to do onsite so it’s a great place for a longer stay (we were only there for a weekend). Wonderful pool and hot tub and the unit we were in was within a 4 min walking distance to the rec center. Only a 10 min drive to downtown Stroudsburg which is lovely, great restaurants. Highly recommend for a poconos getaway, especially for two couples or a family. There were two full baths, plus a powder room. Very well appointed kitchen, a screen porch which was great.
A spacious living area features a light gray sectional couch adorned with navy blue and patterned throw pillows. A vibrant area rug adds color beneath the furniture. A small dining table with chairs is visible in the background, along with a wall-mounted landscape print and sliding glass doors.
Condo in Vernon Township
4.9 out of 5 average rating, 10 reviews

Condo in Vernon Township, NJ

VictoriaRating, 5 stars1 week ago
The place was beautiful and Mohan was a great host. I definitely recommend his place for anyone who is looking for a getaway.
Guest favorite
A cozy living room features a gas fireplace set in a stone mantel, with a wooden panel above. Bright curtains frame the windows, while comfortable seating includes a gray sofa, patterned armchair, and decorative side table. A console table holds a flat-screen TV.
Condo in Vernon Township
4.86 out of 5 average rating, 51 reviews

Spacious Condo w/ View < 1 Mi to Mtn Creek Resort!

ColtRating, 5 stars4 months ago
Great clean place to stay, right across from the ski mountain! Will definitely come back, highly recommend.
The living area includes a comfortable couch and a cozy armchair beside a gas fireplace. A wooden coffee table is centered on a beige carpet, and a flat-screen TV is mounted above the fireplace. Natural light enters through a large window covered with dark curtains.
Condo in Vernon Township
4.78 out of 5 average rating, 50 reviews

Cozy condo in Ski Resort. 2 bedroom/2 bath Unit226

YayoiRating, 5 stars3 months ago
We stayed to ski at Mountain Creek resort. Roger was always very helpful during our stay. We used a car service to get there so that we did not have a space to keep our suitcases before and after check-in/out. Roger has helped us to figure it out smoothly both times. Rooms were extremely clean, the view from the room was great. There is a laundry room in the building. This place is great for a family to stay. Mountain Creek is a wonderful resort, being able to ski and swim in a warm pool. We hope to come back here to ski, and we hope to stay at the same Roger's place.
A spacious living area features a comfortable sectional sofa adorned with red and gray cushions. A large area rug is positioned under a coffee table, surrounded by stylish dining chairs. A wall-mounted television is complemented by a contemporary electric fireplace, enhancing the cozy ambiance.
Condo in Vernon Township
4.56 out of 5 average rating, 133 reviews

Red Lodge Chalet - Ski on Ski off / 3 Bedroom

StevenRating, 5 stars3 weeks ago
Had a great weekend at Marc and Natallia’s Airbnb! Everything was clean and well maintained, and the area was beautiful. I would definitely come back.
Superhost
An indoor swimming pool area is shown, featuring a large, clear pool surrounded by concrete flooring. Several white lounge chairs are neatly arranged along one side, and large windows allow natural light to brighten the space.
Condo in East Stroudsburg
4.88 out of 5 average rating, 8 reviews

Shawnee Village, PA, 2 Bedroom King Depuy #1

MarieRating, 5 stars10 months ago
Had a wonderful time at Jan's place. We celebrated our very first family reunion. Beautiful setting with access to all kinds of amenities. Stay at Jan's... guarantee you won't be disappointed!
Guest favorite
A row of multi-level wooden cabins is nestled among trees, showcasing natural wood finishes. Each unit features large windows and balconies, with exterior stairs leading to the entrances. The surrounding area is enhanced by vibrant autumn foliage.
Condo in East Stroudsburg
4.89 out of 5 average rating, 28 reviews

Wyndham Shawnee Village|1BR/1BA Full Balcony Suite

MelissaRating, 5 stars3 weeks ago
This was a wonderful place to stay. My wife enjoyed the view, the quietness, and the time spent together. We hope to come back soon.
Superhost
A person sits in a canoe on calm waters, arms raised in a gesture of joy. Lush greenery and trees line the riverbank, reflecting in the still water, creating a serene outdoor atmosphere.
Condo in East Stroudsburg

Pocono Haven, PA, 2 Bedroom F # 1

VeronicaRating, 5 stars9 months ago
The place was beautiful and peaceful, kitchen had everything you need to cook, everything was clean and ready for us when we arrived, you have a recreational center with indoor and outdoor pool, arcade, basketball field, but the condo is on a quiet a peaceful area 2 minutes drive from the recreational center, house has all the amenities for a perfect stay. Max was kind and responsive to my questions, I definitely recommend this place.

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