Apartment vacation rentals in Middletown

4.79 out of 5 average rating, 285 reviews

A cozy living area features a gray sofa and ottoman, complemented by an artistic wall decoration. A spiral staircase leads to a lofted space above. Natural light streams in from the window, highlighting the exposed beams and the elegant architecture of the room.

Apartment in East Haddam

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

The exterior of the rental unit is framed by mature trees, with a front porch featuring a railing and rocking chairs. A stone wall lines the driveway, leading up to the entrance. Soft greenery surrounds the area, creating a serene environment.

4.98 out of 5 average rating, 168 reviews

Charming Chester Retreat - Cottage

Home away from Home! Thoughtfully designed 2 bed, 1 bath unit is the perfect blend of style and comfort. The space has been re-designed to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also features a roof deck that overlooks our mature maple trees and a sprawling front porch, complete with rockers. Great for 1-2 couples, small families or group of friends—Ask about our single roll away bed or pack' n' play(s). Kid friendly! New England getaway / Hidden Gem / Retreat

The exterior of Lori Warner Studio/Gallery showcases a vibrant red door framed by large glass windows. A deep blue awning offers shade, while decorative planters with greenery are positioned beside the entrance. Outdoor seating is visible in the background, complementing the inviting atmosphere.

4.93 out of 5 average rating, 372 reviews

Chester Village 'Pied-à-terre' above art gallery

ONE night stays are available for last minute bookings, message us! If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled livingroom w/high ceilings, quiet, private bedroom in back, and w/large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT!!!

4.94 out of 5 average rating, 805 reviews

A bright living space is showcased with wooden floors and white walls. A dark leather sofa faces a wooden coffee table, while a rocking chair invites relaxation. A dining area features a table with four orange chairs, complemented by natural light from nearby windows.

Apartment in Middletown

Quaint 2br apt- 1 block walk to Wesleyan & Main St

Nicely appointed 1st floor 2 BR apt with mid-century modern inspired decor that is a cozy home away from home. House is 1 block from Wesleyan and 2 blocks from food/fun on Main St, so you don’t need to use your car to visit Wesleyan or get to anything in town since the location is very walkable. Laundry, dishwasher, tv with roku, dvd player and dvd’s, books, bluetooth radio, wifi, front porch and back yard seating, close to Rt 9, I-91, Rt 84, Hartford and short drive to beaches/shoreline/I-95.

4.91 out of 5 average rating, 100 reviews

A peaceful view of Paper Goods Pond is captured, showcasing calm waters reflecting the sky. Surrounding trees display vibrant autumn colors, and a grassy area leads down to the water's edge. The serene landscape provides a backdrop for relaxation and connection with nature.

Apartment in Berlin

Pond View Retreat I in Central CT

Comfortable 1 bedroom apt. Centrally located between Hartford and New Haven Near CCSU, UCONN Medical, HOCC, Hartford, Middletown. Perfect for extended stay. Business, nurses, snowbirds. We host short term if available close to requested dates. Separate one bedroom apts. 2nd floor. Washer/Dryer. See our 2nd listing Pond View Retreat II. Clean, safe location. Close to train station, banks, restaurants, grocery stores ,hwy. Relax and enjoy the four seasons over looking Paper Goods Pond!

5 out of 5 average rating, 106 reviews

A spacious living area is characterized by high beamed ceilings and large windows that allow natural light. Furnishings include a round dining table surrounded by six chairs and a comfortable seating arrangement, featuring a decorative rug. A large television is positioned on a wooden stand.

Apartment in Coventry

Hide Away at Rock Farm UConn Private BnB “5 Star”

Enjoy a peaceful stay at The “Hide Away” on Rock Farm. The 1000+ sf of space is surrounded by woods 600ft off the road. Well lit, all amenities of home. Enjoy the private deck on sunny mornings. 5 min walk to Bolton Lakes. Fishing, Kayaking & trails. Central to many locations & venues. See our VIP GUEST BOOK for The Get Away on Rock Farm & The Hide Away at Rock Farm. A no-shoe, clean place, comfortable homey feel. 5⭐️ Needing less space? Visit the Get Away https://www.airbnb.com/h/onrockfarm

4.89 out of 5 average rating, 438 reviews

An open living space showcases a wooden table with candles, surrounded by wooden chairs. A white sofa with decorative cushions is positioned next to a reddish armchair. A coffee table sits central, with a small plant atop a patterned rug. Light illuminates the cozy atmosphere.

Apartment in Glastonbury

Quiet 2 bed room apt w/ private entrance.

NOTE WELL: This light, spacious basement apartment is located in a residential neighborhood in South Glastonbury near the Connecticut River and many good hiking areas, shops, and restaurants. We are working professionals who rise and retire early. We have a large exuberant dog who is fenced (electric) away from the apartment and house entrances and driveway. The space is not appropriate for parties. Do not inquire or book if your life situation is not amenable to this description.

4.9 out of 5 average rating, 168 reviews

The exterior of a single-story apartment features a beige facade with brown trim. A welcoming front door is flanked by potted plants, and a covered porch is visible. Natural light illuminates the surroundings from a clear blue sky.

Apartment in East Haddam

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

4.95 out of 5 average rating, 193 reviews

A round wooden table is set with woven placemats, featuring a white cup filled with frothy coffee. A tall vase with a vibrant sunflower adds a touch of color, while a small tray with assorted snacks is visible in the background.

Apartment in New Britain

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

4.97 out of 5 average rating, 378 reviews

The welcoming exterior of a classic two-story home is showcased, featuring dark siding and white shutters. A well-maintained pathway leads to the entrance, illuminated by a lamp post. Rocking chairs are visible on the porch, with light spilling from the windows, suggesting a cozy atmosphere.

Apartment in Wallingford

Spacious in-law apartment steps from Choate

Private apartment with private entrance. This cute apartment is located in the center of town, close to Choate Rosemary Hall and downtown Wallingford. Very safe and charming neighborhood. Off street parking included. The private space includes a combination living, dining room, and full kitchen. Private bathroom with clean shower and amenities. Beautiful backyard with a pretty patio

4.86 out of 5 average rating, 114 reviews

A cozy living area is highlighted by a gray sofa adorned with blue cushions, paired with a wooden dining table and chairs. Natural light enters through a window, complementing the warm yellow walls and wooden flooring. A ceiling fan adds a subtle touch of comfort.

Apartment in Middletown

Perfect Private "Downtown Village" Apartment

Private Second Floor Rear Apartment of an 1849 historical home in the heart of Middletown, CT. One block walk to Wesleyan University with private parking. Main street also one block away with many great restaurants, and our best local coffee shop (Klekolo) just doors away from your apartment. The House is across from the public library. Stone patio in a lovely fenced in rear yard.

4.82 out of 5 average rating, 164 reviews

Two paddleboats are moored next to a wooden dock, resting on calm waters. The boats feature a blue color with a simple design, and the dock extends towards the lake, reflecting the peaceful setting.

Apartment in Middletown

Lakeside apartment 2.5 miles from Wesleyan campus!

Walk out to your private deck from either the living room or the kitchen. Newly-refurbished apartment in a beautiful, peaceful setting on small lake, suitable for swimming or fishing. Enjoy free use of our paddleboat! This is an in-law apartment attached to our home, so we will be nearby to help with any issues that may arise during your stay.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Middletown apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A covered patio area features comfortable outdoor seating framed by lush greenery. A small table is positioned near the seating, creating a cozy space for relaxation. The well-maintained yard extends in the background, offering a serene setting for outdoor enjoyment.

5 out of 5 average rating, 26 reviews

New, modern studio steps from downtown Chester CT

CraigRating, 5 stars1 week ago

Great place! We stayed here on our wedding night and it exceeded our expectations. Quaint, well maintained and beautifully decorated. It was modern, clean with thoughtful attention to detail. Located near the center of Chester, a true hidden gem on the CT river. Friendly hosts.

Apartment in Downtown Hartford

A spacious living area features a brown leather sectional sofa complemented by decorative yellow cushions. A wooden coffee table with a patterned ottoman sits in front of a television. Large windows allow natural light to illuminate the room, with potted plants adding a touch of greenery.

4.9 out of 5 average rating, 70 reviews

Designer's Den in the Business District

AndreaRating, 5 stars1 month ago

Fantastic home! Our host was incredibly friendly and quick to respond. Location is very walkable with lots of things to do and places to eat. Had a few amenity issues but our host was quick to offer alternative options and additional services. Would love to be back :))

Apartment in Killingworth

An aerial view of the farm showcases expansive green grounds interspersed with tree cover and pathways. Several fenced areas and horse barns are visible, along with well-maintained fields. The surrounding nature creates a serene environment, inviting a sense of peace and relaxation.

4.9 out of 5 average rating, 48 reviews

Life on the Farm

BrooklynRating, 5 stars2 weeks ago

We loved our stay here for when we visited New Haven! The place was clean and worked perfect for our dog! We loved the farm outside and the peaceful and private area outside. Would stay here again!

4.96 out of 5 average rating, 28 reviews

A cozy living area is presented with a neutral color palette. A comfortable sofa is draped with a textured throw, and an organic wooden coffee table is centered within the space. Art prints adorn the walls, while natural light gently illuminates the room.

Apartment in Westbrook

Meadowview & Pondside Retreat

LaurenRating, 5 stars1 week ago

We had a lovely stay at this beautiful home! We actually ended up having pictures taken in the backyard because of how gorgeous the scenery is. Becky was super responsive and friendly. Definitely would love to come back! :)

4.9 out of 5 average rating, 31 reviews

A cozy bedroom is featured with a spacious bed dressed in white linens and decorative pillows. A soft, patterned throw covers the bed. Natural light enters through a large window draped with sheer curtains, and a decorative sign hangs on the wall.

Apartment in Wallingford

Seasons Hospitality Cozy 1BR Waiting for you C1

DanielRating, 5 stars1 week ago

Awesome weekend with the family. Property was no more than 10-15 minutes from any graduation or other gathering we attended. Thanks.

4.96 out of 5 average rating, 84 reviews

A spacious living area features a large sectional sofa adorned with red cushions, complemented by a coffee table and side tables. Bright light floods the room through the sliding glass doors, opening to the outdoor deck. A staircase leads to a lofted area, enhancing the open feel.

Apartment in Guilford

Cozy Private Lake Q Retreat

JenniferRating, 5 stars3 weeks ago

Great little spot. This rental has everything you need. Forget something-they got it. Very clean and modern with thoughtful touches. Had an extended stay here and extended for longer. 1 bedroom with loft that owner made into another bedroom for me. Loved it. Great deck, stunning lake view from all the windows. Owner very responsive to any needs. 100 percent recommend. Neighborhood lovely and quiet. Amazing respite.

4.78 out of 5 average rating, 18 reviews

The open kitchen features dark cabinetry, light countertops, and essential appliances, including a stove and refrigerator. A cozy living area is visible in the background, furnished with a blue sofa and a simple table. Natural light filters through the window treatments.

Apartment in New Britain

Comfy Equipped Family Suite Near Everything

DarrenRating, 5 stars2 months ago

Absolutely fantastic place to stay if you are ever visiting or traveling I would highly recommend this place everything about this stay makes you feel at home !! Host very respectful and responsive anything you need (if needed ) she’s right there to guide you and another thing is this place is very convenient around shopping centers , grocery stores, Planet fitness, etc !! HIGHLY RECOMMENDED ‼️‼️‼️‼️

5 out of 5 average rating, 30 reviews

A large two-story house features a dark exterior with stone accents and multiple gabled roofs. Large windows allow ample natural light to enter, while a wooden front door adds a welcoming touch. Lush greenery surrounds the property, enhancing its natural setting.

Apartment in Branford

Stedley Creek

LorettaRating, 5 stars1 month ago

Selestria was super kind & supportive! She made us feel welcomed and made herself available for calls if needed. The home was clean and nice looking :)

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Private apartment rentals

Apartment in Downtown Hartford

A spacious living room features a comfortable couch adorned with colorful pillows. A potted plant adds a touch of greenery beside a contemporary armchair. Light filters through sheer curtains, and a soft area rug covers the hardwood floor, creating a cozy atmosphere.

4.92 out of 5 average rating, 52 reviews

Mod-Chic 1 Bedroom with Free Parking & Wifi

ValareeRating, 5 stars3 weeks ago

I really enjoyed my stay. It was easy to access and very clean. I was very comfortable. Had everything I needed.

5 out of 5 average rating, 18 reviews

A spacious living area features a dark sectional sofa adorned with soft pillows and a cozy green throw. A small wooden tray is placed on the armrest. A modern kitchen and dining area are visible in the background, highlighting a neutral color palette.

Apartment in Andover

Beautiful 1 Bdr Oasis|10 miles to UCONN|473mbs|W/D

LindaRating, 5 stars1 month ago

One of the very best Airbnb's I have stayed in. Special attention paid to the little details that make the stay extra nice for guests. spacious and comfortable. I will definitely be back.

4.69 out of 5 average rating, 16 reviews

A bright, inviting living area features a green couch and a wooden coffee table atop a decorative rug. A desk is positioned next to a window, where natural light filters through sheer curtains. Plants add a touch of greenery to the space.

Apartment in Manchester

Crested One Place - Heat & Free Parking included

JuanRating, 5 stars2 months ago

Godfrey was an incredibly responsive host! We arrived earlier than planned, and he was very accommodating. The home was spotless, well-organized, and the bed was exceptionally comfortable. Thank you for hosting us!

A cozy outdoor fire pit area features four Adirondack chairs gathered around a warm fire. Soft lighting from string lights above enhances the tranquil setting, with natural greenery surrounding the space. Guests are seen enjoying conversation, adding to the inviting atmosphere.

4.99 out of 5 average rating, 95 reviews

The Millhouse Downtown Chester

PhilipRating, 5 stars1 month ago

This is our second time staying at this property. Four of us were visiting people in the area and The Millhouse is a great location to explore the area, with nice places to eat only steps away on Chester Center Main Street. The stream-side location makes it a very unique experience and the interior of the property is very nicely decorated and maintained.

A charming historic house is presented, featuring rustic wooden shingles and a distinct gabled roof. The front yard is enclosed by a white picket fence, with neatly trimmed shrubbery and seasonal flowers. An American flag waves gently in front, adding a touch of character.

5 out of 5 average rating, 22 reviews

The Little Chestnut.

JeannyRating, 5 stars1 month ago

My husband and I just got back from a 4 night stay at The Little Chestnut and it's now added to my Airbnb faves. It's adorable! Communication with Samantha was great- she was super responsive and friendly. Self check in was a breeze with the info provided and the place itself was cozy and welcoming. It sits above a bookstore which I love since I'm an avid reader. The living room area was spacious and the small vintage desk in the corner was perfect for working from my laptop. It was so convenient to have a full kitchen to cook meals in (bring your own spices, food, etc.) as well as a washer & dryer to do laundry before we left. The bathroom is located upstairs where the comfy bedroom is and while tiny (the shower may be cramped for taller people), it was cute and clean. The apartment is also a quick few minutes walk to the quaint main street where all the restaurants,shops,and galleries are (The Village Bistro and Grano Alto for dinner were awesome). I highly recommend staying here!

4.98 out of 5 average rating, 104 reviews

A serene garden area is seen, featuring lush green grass and vibrant flowerbeds with orange blooms. A tranquil pond is visible in the background, surrounded by trees and natural landscaping, creating a peaceful outdoor setting.

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

JudyRating, 5 stars2 weeks ago

Dawn and Bob’s place is one of the top Airbnb’s we have stayed in! Top notch in every way. It was spotless, comfortable and had everything we needed. And on top of that Dawn and Bob were the most friendly hosts we have met! I would recommend this Airbnb without reservation and will be back whenever we are back in CT!

4.89 out of 5 average rating, 44 reviews

A cozy pool table area features a vibrant red felt table centrally located. A blue couch with decorative pillows is positioned nearby, alongside a stone-top table. Natural light flows through large windows, illuminating the warm wooden ceiling and brick wall, enhancing the inviting atmosphere.

Apartment in North Haven

Charming Dog Friendly Suite On Scenic Property

RuthanneRating, 5 stars5 months ago

Nice place located in a beautiful secluded house in a safe neighborhood. Gorgeous property. Our dogs were allowed and they were very comfortable. The amenities were exactly as described. Extremely clean and well maintained. The place was easy to locate and easy to access. It is convenient to many local stores and restaurants. Great, responsive hosts!

5 out of 5 average rating, 139 reviews

A bright and modern kitchen area features white cabinetry and stainless steel appliances. A large island is equipped with seating for three, while a cozy living space with two leather chairs is visible in the background. Natural light filters through multiple windows.

Apartment in New Haven

The Winchester House at Science Park-Yale

ChrisRating, 5 stars3 weeks ago

This is a superior rental space and host. Michael stocked the refrigerator and gave us free use of two bikes which I used a lot during our stay. The space was clean and fully updated. The location is right near a bike path and the Yale campus is very close by. The only glitch we had during our stay was that I accidentally set the ADT alarm and couldn’t get it to reset properly. I didn’t hear from Michael, so I got in touch with Airbnb folks who couldn’t help me. I eventually figured it out and was able to leave the unit without setting off the alarm. Other than that, it was a completely amazing stay!

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Apartment rentals with a hot tub

Apartment in Downtown New Haven

A spacious sleeping area is highlighted by a large bed featuring a decorative headboard with an intricate blue pattern. Two bedside tables hold modern lamps, and a crib is positioned nearby, offering a family-friendly environment.

4.75 out of 5 average rating, 141 reviews

Luxury Penthouse Minutes to Yale

AbiolaRating, 5 stars3 weeks ago

My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.

A charming garden pathway is lined with vibrant flowers and lush greenery, leading to an archway covered with climbing plants. Stone stepping stones create a natural flow through the garden, while the well-tended landscaping surrounds the white exterior of the adjacent building.

Apartment in Colebrook

5 out of 5 average rating, 25 reviews

Rural retreat in Colebrook CT

CarrieRating, 5 stars28 months ago

Marge was an amazing host who went to effort to ensure we were comfortable and taken care of. For example, in advance of our arrival she asked what type of bread and juice we preferred and if we wanted milk or cream for our coffee. She providd fresh eggs and even sent a dozen to our daughter who lives down the street. The apartment was welcoming, clean and cozy. The kitchen and pantry were well-supplied to meet our needs. We will definitely stay at Marge's next time we visit our daughter.

The bedroom features a spacious bed adorned with a patterned quilt and an arrangement of decorative pillows. Two bedside lamps provide soft lighting. A floral artwork hangs above the bed, complemented by butterfly prints on the adjacent wall. A round window offers additional light.

Apartment in Norwich

4.67 out of 5 average rating, 42 reviews

Cozy spa condo with pools near Mystic/Mohegan Sun

TiffanyRating, 5 stars2 weeks ago

The place was very clean and easy to access. It felt safe and had great amenities. The extra large bed was so nice and the neighbor hood was super cute!

KatherineRating, 5 stars4 months ago

A spacious bedroom features a four-poster bed dressed in crisp white bedding, accompanied by decorative mirrors and warm-toned accent pillows. A cozy ottoman is placed at the foot of the bed, with a small side table displaying a welcome message and a plant. Soft lighting enhances the inviting feel of the room.

Apartment in Norwich

Cozy Corner, by the Spa

Amazing stay! Relaxing and our host was very communicative

A spacious living area features large windows allowing natural light to fill the room. A light-colored sectional sofa and an armchair are complemented by a decorative throw. A coffee table sits at the center, with a television positioned on a media console. Potted flowers add a touch of vibrancy.

Apartment in Stratford

New place to stay

River's Edge Retreat

NishaRating, 5 stars1 month ago

We enjoyed our stay. The space was amazing and spacious for five adults. Our experience with Jose’s listing was outstanding, from the cozy bed to the stunning views every morning and the timely response from Jose. It made the family trip a memorable one!

An open studio space features a queen bed with floral bedding, a cozy seating area, and a stone fireplace. Large windows provide natural light and reveal views of the outdoors. A dining area and bar with seating are visible, enhancing the inviting ambiance.

Apartment in Montville

4.74 out of 5 average rating, 122 reviews

Cozy Studio: Indoor Hot Tub & Inground Pool Access

JillianRating, 5 stars1 month ago

If you are looking for a peaceful stay with an absolutely gorgeous view I fully recommend this place! The sound of nature as you look down the mountain full of beautiful trees and landscape! The hot tub in the space was relaxing and perfect! Everything you need in your little area. Also, Al was an absolute pleasure. He was sweet, very accommodating, and gave great recommendations! I would highly recommend and I would love to return in the fall to see the view in color!

5 out of 5 average rating, 5 reviews

An outdoor swimming pool is surrounded by a spacious patio, with several lounge chairs placed along the edge. Colorful flower beds and trees line the area, adding greenery and vibrancy. The pool features clear blue water, reflecting sunlight, and is situated within a well-maintained community space.

Apartment in Norwich

Villa in Norwich

NicoleRating, 5 stars5 days ago

Rosemarie’s place is lovely and the resort has amazing amenities!!! The villa was VERY clean! Only 5 mins from Mohegan Sun! Check-in was very simple and the villa was quiet and peaceful. We had a great weekend stay!