Apartment holiday rentals in Middlesex County

Find and book unique apartments on Airbnb

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Popular amenities for Middlesex County apartment rentals

Weekly apartment rentals

Top Guest favourite
Apartment in Old Saybrook
4.98 out of 5 average rating, 53 reviews

Charming Center of it All Location

StephenRating, 5 stars13 months ago
Awesome space. Roomy, comfortable, well equipped. Very walkable and close to town, yet quiet considering being right on Main Street. Third time staying at this location and looking forward to another visit.
Guest favourite
Apartment in Chester
4.85 out of 5 average rating, 61 reviews

Gingerbread Apartment, Walk Downtown

KellieRating, 5 stars2 months ago
Karli's third floor apartment was the coziest place for me and my best friend's Girl's Night. We stayed during a snowstorm and Karli made sure the driveway was shoveled and the stairs were salted and cleared for us. The apartment itself was so cute and had everything we needed for a cozy night. Even though it was snowing, we still ventured out downtown which was a quick 5 minute walk, and it was absolutely magical in the snow. We would absolutely book Karli's place again!
Top Guest favourite
Apartment in Middletown
4.97 out of 5 average rating, 34 reviews

Your Sweet Spot in Middletown CT

JessicaRating, 5 stars1 week ago
My husband and I enjoyed our stay at the Sweet Spot. It’s a cozy studio in-law apartment built off the main home. The apartment was clean and well kept. We had the pleasure of meeting our host, Bridget, and she shared that they had recently converted the space from a sun room into an apartment. We didn’t have the opportunity to meet Collette. Location is prime as it’s close to downtown Middletown, Wesleyan University, as well as easy access to Route 9. Being close to Main St. made it easy for us to get up in the morning and grab a quick breakfast before heading out for the day. The neighborhood they are in is peaceful, located in a residential area. Would book again.
Top Guest favourite
Apartment in Guilford
5 out of 5 average rating, 6 reviews

Apt in Historic Four Elms steps from the Green

MarieRating, 5 stars3 weeks ago
It's always a little bit of a let down when you stay at an Airbnb and you can tell that everything was done relatively cheaply. Rarely does it feel as nice as a hotel stay. Adam and Rachel's place was the first Airbnb we've stayed at in recent memory that felt just as nice as a hotel. It was incredibly clean, well decorated, and had the extra touches that you could tell was done with care (versus just an investment property). Very walkable to the Guilford Green - you can't beat location. The stairs were a little challenging with baby stuff (they are narrow) but we were warned and it was worth it. Highly recommend their place!
Top Guest favourite
Apartment in Guilford
4.97 out of 5 average rating, 37 reviews

Charming loft in Guilford

HubertaRating, 5 stars5 months ago
Minerva has been a lovely host who always responded asap and helped whenever I had questions. She was also really generous when I messed up my day of departure and left the apartment a little later than agreed upon. Thank you for being such welcoming hosts.
Guest favourite
Apartment in Clinton
4.89 out of 5 average rating, 9 reviews

Bright & Cozy Loft Near Beach

Wayne WilliamRating, 5 stars3 days ago
We had a very comfortable stay, and she was very quick with her responses when we had questions . The place was roomy and clean!
Apartment in Middletown
4.54 out of 5 average rating, 24 reviews

Private Apt in Middletown-Wesleyan

NaluRating, 5 stars1 week ago
We had a great time staying here while visiting Wesleyan. A great location close to campus.

Private apartment rentals

Top Guest favourite
Apartment in Clinton
4.98 out of 5 average rating, 45 reviews

Shoreline Oasis

AlisonRating, 5 stars2 days ago
Had a lovely stay at Catherine’s. It was even sweeter in person. Appreciate all of the little details and love all the plants. Felt very cozy and had everything I needed!
Guest favourite
Apartment in Killingworth
4.8 out of 5 average rating, 10 reviews

Cozy & Romantic CT Hideaway: Forest & Beaches

DamianRating, 5 stars4 months ago
Lovely and charming location. Full of New England charm. The guest apartment was spacious, comfortable and very well appointed with all we needed. Definitely expecting to stay again when in the area.
Top Guest favourite
Apartment in Westbrook
5 out of 5 average rating, 7 reviews

Private Guest Suite Water Views

TulsiRating, 5 stars4 months ago
Great cozy place with a lovely view of the marsh from the bedroom window. Bruce was a kind and thoughtful host, the place was very clean and easy to get in and out with clear instructions and labels on everything. Thank you !
Guest favourite
Apartment in Guilford
5 out of 5 average rating, 6 reviews

Lakefront Country Oasis

SergioRating, 5 stars10 months ago
Margie’s place is an amazing hidden gem. The inside is very clean and comfortable. The outside is an experience of its own. The lake will drop your blood pressure immediately. Gorgeous surroundings. The dogs are friendly and lovable. We will be back! 👍🏼
Top Guest favourite
Apartment in Clinton
4.99 out of 5 average rating, 68 reviews

Cozy Shoreline Getaway

FrederickRating, 5 stars4 months ago
Comfortable accommodation. Everything you could ask for. We we’re lucky to stay longer over the holiday. Dave and Charlene are great hosts, great communicators. We plan to stay at this location whenever we vist family in Connecticut.
Guest favourite
Apartment in Middletown
5 out of 5 average rating, 33 reviews

Newly Renovated 2-bedroom Near Wesleyan-Middletown

LarisaRating, 5 stars4 days ago
This was the best Airbnb I’ve stayed in to date! Beautiful space, pristine, clean, had everything we needed and more! Kid friendly which was necessary for our family with 3 little ones! Tom really thought of everything. Anything we needed was there! And Tom was very responsive to any questions I had during the stay! I especially enjoyed the games in the living room that were kid friendly. The backyard was beautiful and my girls enjoyed running around. The location was perfect for us as it was very close to the wedding venue that was our reason for being in town. The whole family slept comfortably and peacefully through the night, including our 5 month old! I cannot speak highly enough of this place. Worth every penny we spent!!
Guest favourite
Apartment in Guilford
5 out of 5 average rating, 41 reviews

Historic 2 bdrm apartment in downtown Guilford

LeslieRating, 5 stars5 months ago
My daughter and her husband stayed at this lovely location over Thanksgiving- needed some extra accommodations beyond our local home. They reported that it was a perfect place for them - clean, spacious, walkable and nicely furnished. We will definitely return when in need of additional accommodations. Highly recommend.
Superhost
Apartment in Middletown
4.85 out of 5 average rating, 27 reviews

Cozy 2BR/1BA Apt | Close to Wesleyan & CT River

RebeccaRating, 5 stars2 months ago
This is one of the best Air Bnbs i have stayed at. Checking in was simple. When i first walked in, i couldn’t believe the space, the brightness and the cleanliness. It felt like home! You have a reserved parking spot which is great! The owners were quick to respond with any questions i had. If i could, i would have stayed longer!

Apartment rentals with a hot tub

Superhost
Apartment in New Haven
4.75 out of 5 average rating, 140 reviews

Luxury Penthouse Minutes to Yale

AmandaRating, 5 stars4 months ago
Great location. Easy check in and out.
Apartment in Colebrook
5 out of 5 average rating, 25 reviews

Rural retreat in Colebrook CT

CarrieRating, 5 stars26 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.
Guest favourite
Apartment in Southampton
4.96 out of 5 average rating, 90 reviews

Private w/Hot tub Fire Pit Coffee Bar

TaylorRating, 5 stars1 day ago
We stayed for our honeymoon - long weekend and first time Hamptons visitors. Very clean, organized and cozy space with nice decorations. All amenities listed were available. We really enjoyed the hot tub and firepit, very peaceful and private area. You should have a car to get around to restaurants, shops, and other outdoor activities. Lots of areas were walking, bike, and scooter friendly. There were so many beautiful views of the water!! Would stay here again, great value.
Apartment in Norwich
4.74 out of 5 average rating, 35 reviews

Cozy spa condo with pools near Mystic/Mohegan Sun

LandenRating, 5 stars2 months ago
I really enjoyed my stay at Sherri's place. Something about it felt more like "home" than a rental property which I appreciate. I was able to enjoy the hot tub and sauna. The hours aren't posted but it was open pretty much the entire time I was there and not crowded. I also felt like there were a lot of extras at Sherri's place for cooking. There were two coffee makers and lots of spices. It was very convenient and there was to do around the area.
Apartment in Montville
4.75 out of 5 average rating, 120 reviews

Cozy Studio: Indoor Hot Tub & Inground Pool Access

ShainaRating, 5 stars2 months ago
Everything was amazing! Property owner was friendly and welcoming! Hoping to plan another trip to this spot it was truly an amazing weekend! Thank you!!!
Apartment in Norwich
5 out of 5 average rating, 3 reviews

Golf course Villa

JulieRating, 5 stars1 month ago
Loved my stay at Rosemaries villa. It was beautiful and peaceful. Will definitely return!
Top Guest favourite
Apartment in Waterford
5 out of 5 average rating, 26 reviews

Garden Suite: Private, Near Mohegan Sun & USCGA

NicoleRating, 5 stars2 days ago
We really enjoyed our stay here. It was clean, cozy and the airbnb is well stocked with items! If we are back in this area, we would definitely stay again.

Destinations to explore