Some info is shown in its original language. Translate

Condo vacation rentals in Middletown

Find and book unique condos on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Middletown condo rentals

Weekly condo rentals

Guest favorite
The entrance of a building is framed by large, leafy trees, creating a dramatic pathway. Soft lighting highlights the entrance doors, while benches provide a welcoming seating area. The ambiance is serene and inviting, enhanced by the surrounding greenery.
Condo in Montauk
4.88 out of 5 average rating, 43 reviews

Romantic and unique treat in Historic Montauk.

JaimeRating, 5 stars7 months ago
Muy buena atención de Gregg y muy amable a la hora de nuestra llegada, muy atento una vez que llegamos! El departamento era muy bonito y todo estaba en buenas condiciones, la vista que tiene el hotel es simplemente espectacular!
A modern kitchen area features white cabinetry and stainless steel appliances, including a built-in microwave and oven. Natural wood flooring provides warmth, while a dining space with black bar stools and a small table is illuminated by natural light from nearby windows.
Condo in Stonington
4.82 out of 5 average rating, 49 reviews

Mystic Refuge w/ Patio < 1 Mi to Downtown!

LisaRating, 5 stars7 months ago
Thank you for allowing us to stay at your rental. Very convenient location, very neat, and modern. Love the slider door to the one bedroom. We were informed about the long term renter on the second floor in the description, however the upstairs tenant was very active in the early hours (1am, 3am) and we were woken up each night by the sounds of heavy walking, tv, and conversation. It was not all night in duration though. Overall, it didn’t dampen our stay at the rental but if someone has a baby or toddler, they may have an issue with the sound from above.
A neutral-toned sofa is positioned against a light wall, complemented by a textured cream throw and a striped accent pillow. A framed wall hanging with the phrase 'Welcome Home' adds a touch of warmth and inviting ambiance to the living space.
Condo in South Norwalk
4.83 out of 5 average rating, 23 reviews

*New Studio in the heart of Downtown Norwalk*

ToniaRating, 5 stars1 week ago
Really enjoyed our stay in Norwalk. Be sure to pay attention to the fact that the unit is on the 3rd floor, and there is not an elevator. It was easy to navigate and the stairs just added to our daily exercise routine. Perfect! We did have a parking snag that was of my own doing. So if you have a car be sure to provide the CORRECT license plate info. Nichole helped resolve it very promptly. FYI parking is on the lower level of the parking structure behind the unit.
Condo in Norwich
4.8 out of 5 average rating, 45 reviews

Norwich spa retreat on golf course near casinos

NicoleRating, 5 stars1 month ago
Everything was amazing! Comfortable, clean space and was a great landing zone for a fun weekend. Definitely want to come back and definitely prefer to a casino hotel.
A welcoming living area features large arched windows allowing natural light to fill the space. A cozy pink sofa is accompanied by a small side table and a tall indoor plant. A swing chair hangs nearby, while a patterned area rug complements the wooden flooring.
Condo in South Norwalk
5 out of 5 average rating, 8 reviews

Unique studio on Washington St

NaomiRating, 5 stars1 month ago
Thank you Heather for the wonderful stay. This spot is truly unique and charming, decorated with impeccable taste. There's very easy access to all the best South Norwalk has to offer. Something that might be helpful for other guests to know in case you're visiting on a weekend is that there is a bar downstairs that plays loud music, HOWEVER the street has an 11pm noise ordinance so the music will not go past then. If you plan to go to bed early, I suggest earplugs and/or a small white noise machine like the ones you can buy on Amazon for $20. The stairs to the loft bed are a little steep so just be aware if you have any mobility issues. None of these things detracted from my stay but wanted to share some info in case it's helpful! This place is a well-kept, clean and cozy gem with a sizable kitchen and bathroom.
A spacious living room showcases large floor-to-ceiling windows, allowing natural light to illuminate the space. Comfortable seating is arranged with a sleek coffee table nearby, and calming decor enhances the modern atmosphere. The television sits on a minimalist console, providing an entertainment option.
Condo in Wooster Square
4.86 out of 5 average rating, 22 reviews

Luxurious 1B, high-ceiling loft in New Haven.

MadeleineRating, 5 stars10 months ago
Linhang's Airbnb is the perfect spot for exploring all of New Haven, but especially Wooster Square and Little Italy. It's within walking distance to amazing restaurants and downtown. Easy check in, well furnished, and clean and comfortable. Linhang is a responsive and friendly host.
A covered porch area features seating with wicker furniture and decorative potted plants. Natural light enters through large windows, enhancing the inviting space. The walls are adorned with light-colored paneling, complemented by a vibrant blue door and accents.
Condo in Springfield
4.78 out of 5 average rating, 50 reviews

2 Bedrooms Mins to Six Flags, MGM, & Free Parking

CarolRating, 5 stars5 months ago
Place was exactly as listed. Clean and very comfortable. Host was very responsive. Having the driveway was great too! Close to everything downtown We will stay again

Pet-friendly condo rentals

Guest favorite
Condo in Litchfield County
4.95 out of 5 average rating, 21 reviews

Pacer's Pasture

CerayeRating, 5 stars3 months ago
Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!
A spacious sleeping area features a large bed with a sleek headboard positioned against a light-colored wall. Two bedside tables are placed on either side of the bed, complemented by a dark wood dresser set against one wall. Natural light enters through partially covered windows.
Condo in Enfield
4.4 out of 5 average rating, 10 reviews

Entire house - 4 Bedroom-Enfield

HunterRating, 5 stars5 months ago
Everything I needed for my work trip👍👍👍 Clean and cozy stay
Superhost
A spacious living area features large glass doors leading to a balcony, allowing natural light to fill the space. Two comfortable sofas in neutral tones are arranged around a coffee table, complemented by a simple area rug. A decorative plant adds a touch of greenery to the setting.
Condo in Hartford
3.75 out of 5 average rating, 4 reviews

Beautiful 2 bedrooms/ 2 bath Condo

BrentRating, 5 stars115 months ago
Sheryl was great. I was in town for a conference and my schedule got thrown off by traffic on 95. She was very understanding and flexible with making my arrival time work. Once we met to get keys and a quick tour of the place she remained a phone call away but otherwise left us to enjoy the space. The other inhabitants of the place were very laid back and nice - that being said I was so busy with a conference that I was barely around. Not the Ritz but a HUGE savings over staying at any hotel downtown even if it's not right downtown. Splurge on some cabs and you are still saving money.
Superhost
Condo in Fairfield
4.83 out of 5 average rating, 139 reviews

Cozy Condo by Fairfield U/SHU | Patio | Wshr/Dryr

RobertRating, 5 stars2 weeks ago
This was our second stay at Dariel’s place. It is perfect for our family and I always check to see if it is available when we are visiting the area. It is spacious yet cozy, and well-appointed. It is easy to get to, and central to both sides of town.
Condo in New Haven
4.77 out of 5 average rating, 87 reviews

Chateau Blanc Yale

JaidelyzRating, 5 stars1 month ago
Our stay was a wonderful experience. The host was very helpful and accommodating. Would stay here again! 10 out of 10.
An open living area displays modern furnishings, including a sofa and a television. A dining table is positioned nearby, and a plush area rug adds warmth to the space. A bright bedroom is visible through an open doorway, featuring a spacious bed and natural light from large windows.
Condo in Downtown Hartford
4.61 out of 5 average rating, 59 reviews

Stylish Downtown Hartford|Laundry|ConventionCenter

Ajah MarleyRating, 5 stars2 months ago
The next time I plan to visit Connecticut, I will definitely consider staying here again. The location was fantastic, offering beautiful views of downtown Hartford. It was a peaceful area with friendly neighbors, and the front desk staff was incredibly helpful. The only downside I encountered was that when I first walked into the apartment, it had a musty smell in the hallway due to a lack of air fresheners, and the TV remote wasn't working. However, after I reached out to the staff about the issues, I received new batteries and a wall plug from his assistant in less than 10 minutes. Unfortunately, the remote still didn’t work, so I ended up using the Roku remote on my phone. Coming from a real estate background, I’d say the place is a bit overpriced, mainly due to the building’s condition; it feels somewhat rundown. Still, I’d rate it a solid 8.8 out of 10 overall. Brain thanks for hosting me.
Condo in Downtown New Haven
4.84 out of 5 average rating, 55 reviews

Charming Studio| Near Yale| Downtown New Haven

Matthew HoraceRating, 5 stars2 weeks ago
An impeccable stay, so much so that I’m actually sad to leave. A very convenient location that is a five minute walk from the campus, and anything else is extremely close by. Clear and efficient communication, clean and organized space, will 100% stay again
A bright entryway leads to a dining area furnished with a round table and wire chairs. Natural light enters through the front door, illuminating the space. A floral centerpiece adorns the table, while a contemporary light fixture hangs above.
Condo in New Milford
4.75 out of 5 average rating, 28 reviews

Lovely Modern 2-bedroom condo near Candlewood Lake

VitoRating, 5 stars18 months ago
The house was very clean and modern. It had everything we needed for a weekend stay. The location is perfect! It's very close to downtown New Milford and restaurants. Would definitely recommend staying here!

Condo rentals with a pool

Top guest favorite
The main living area features a comfortable seating arrangement with patterned armchairs and a gray sectional sofa. A round coffee table sits in the center, complemented by dark poufs. Natural light enters through large windows, and a cozy fireplace adds warmth to the space.
Condo in Norwich
5 out of 5 average rating, 33 reviews

Modern Loft Villa, 1 mile to Mohegan Sun

BonnieRating, 5 stars1 month ago
We had a wonderful stay. The house was beautiful and clean and had everything we needed. Erin was so easy to communicate with. I would recommend this house for anyone visiting the area.
Superhost
An aerial view captures the property layout, featuring landscaped gardens, a heated pool, and multiple buildings. The proximity to the beach is evident, with sandy shores visible in the distance. Access roads and parking areas are clearly outlined, enhancing the sense of space.
Condo in Montauk
5 out of 5 average rating, 12 reviews

Second Floor Corner Unit Overlooking the Ocean

VishnuRating, 5 stars6 months ago
A brief stay but a great stay. It was offseason but we got lucky with sunny October weather. The stay was less than a 5 minute drive from the main village with tons of shops, cafes, etc.. the room itself had a beautiful ocean view and was very clean and comfy. Nice shower, comfy beds, plenty of linens and towels provided. Parking included. Overall a very nice stay.
Guest favorite
An expansive hallway features arched doorways and rustic wooden beams overhead. Potted plants add greenery, while large windows dressed with floral curtains allow natural light to illuminate the stone floor. Comfy seating arrangements are positioned along the walls, creating inviting spaces for relaxation.
Condo in Montauk
4.89 out of 5 average rating, 28 reviews

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

MarielRating, 5 stars3 months ago
Mark's place was exactly what I was looking for to ring in the New Year in style, comfort and complete relaxation! I was able to start each day with a quiet cup of coffee and then head directly to the beach for a long morning walk (just a short drive away). Montauk Manor is an absolute hidden gem for a winter break and the indoor pool and hot tub are a rare find in the Hamptons. Check-in/out could not have been any easier and the Manor staff are wonderfully welcoming and friendly. There were still a good number of local shops open, including Left Hand Coffee. 100% recommend for all seasons and will eagerly book again!
Top guest favorite
Condo in Norwich
4.98 out of 5 average rating, 102 reviews

CASiNO, Spa, Hot Tub, Pool, Private Villa, Kingbed

TattianaRating, 5 stars2 days ago
Kim’s place was perfect for what me and my daughter needed. We were in the area celebrating her 15th birthday. The villa was clean, and quaint. The decor of the room was peaceful and warm. And most importantly it was CLEAN, no complaints! Kim was responsive and proactive in her communication. Will definitely visit again in the future and recommend to any friends and family who might travel that direction.
Guest favorite
A soft green couch features two white, decorative cushions, positioned beneath a large pink cherry blossom tree. A warm, glowing neon sign reading 'Villa Maisonet' adds a welcoming touch to the space, highlighting the charming decor.
Condo in Norwich
4.96 out of 5 average rating, 28 reviews

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi

JessicaRating, 5 stars1 week ago
Amazing stay!! Beautiful home, clean, had everything we needed. Quiet place as well!! Only thing the heated outdoor pool was closed due to maintenance during our stay, but everything else was perfect! Will definitely be staying again!!
Superhost
Condo in Montauk
4.89 out of 5 average rating, 9 reviews

Endless Summer Studio Condo w Balcony Bayview

StephenRating, 5 stars20 months ago
We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.
Superhost
A cozy living area is furnished with a beige sofa, a round wooden coffee table, and stylish light blue armchairs. A large window allows natural light to fill the space. Potted plants add a touch of greenery, creating a relaxed atmosphere.
Condo in Old Saybrook Center
4.89 out of 5 average rating, 72 reviews

Seashore getaway - CT shoreline

JulieRating, 5 stars3 months ago
Thanks Lauren! We enjoyed your lovely place!
Top guest favorite
The historic Norwich Inn is depicted, featuring a brick exterior adorned with green ivy. A grand entrance with white columns and decorative details is visible, surrounded by landscaped foliage. The sky above shows scattered clouds, contributing to the serene ambiance.
Condo in Norwich
5 out of 5 average rating, 10 reviews

Villa @ The Spa at Norwich Inn near Mohegan Sun

PeteRating, 5 stars2 months ago
We had an absolutely wonderful stay at Villa Azul! The home is beautifully decorated with a calming, relaxing vibe—perfect for a peaceful getaway. Everything was spotless, and the thoughtful, homey touches made us feel right at home. It was the ideal retreat for some much-needed relaxation. We also loved the nearby Norwich Spa, where we enjoyed fantastic spa services, and the area has so many great restaurants and entertainment options, especially at Mohegan Sun Casino. There was always something fun to do! Jen was a fantastic host-communicative, helpful, and so welcoming. We’ll definitely be returning for another stay. Highly recommend Villa Azul for anyone looking for a comfortable and relaxing getaway!

Destinations to explore