
Condo holiday rentals in Middlesex County
Find and book unique condos on Airbnb
Top-rated condo rentals in Middlesex County
Guests agree: These condos are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlesex County condo rentals
Weekly condo rentals

My Sweet Apartment
Mihaela’s unit was comfortable and laid out well for us traveling with two small kids. We were able to spread out and have a kidnin each room. The beds were comfortable and Mihaela was responsive and really friendly. I was surprised by how light a basement unit was during the day too. Two things to note which were not a problem for us are that the kitchen is very small and it is not very close to the T stop. We had a car and had meals with family so not an issue for us but just a heads up for others. If you are ok getting around and mostly bringing in food/eating elsewhere, then this is a lovely spot and there is even a nice little outdoor spot in the yard to hang in. Also the driveway was very convenient and the instructions to get into the unit were very easy!

Cozy Top floor apt by St Elizabeth, BU, BC w/ Park
This is a lovely, clean, third floor apartment in a quiet and attractive neighborhood. The beds are very comfortable and the kitchen is great for light cooking. We enjoyed the view out the back window, and the neighborhood turkey roosted in the tree one night(!)

Modern & Stylish 1-BR Condo near Downtown
Great place for our trip to Boston! Quick drive into the city. The space had everything we needed. Highly recommend.

Stunning Waterfront Condo with Boston Skyline View
We had an amazing stay. The home looks as depicted in the photos. Beautiful spaces indoors and out. We were very comfortable and had everything we needed. The property manager, Jay, lives nearby and came over upon our arrival to show us around the property and make suggestions for things to do in the area.

Bright Spacious 3Br, Mins From Downtown, Parking
We stayed at Elena's apartment for a month and found it very comfortable for a long term stay. Elena was always responsive and was quick to troubleshoot a minor issue at the start of our stay. She also kindly let us check in early when we arrived during a snowstorm. The parking space is a great bonus since we only needed our car when we decided to do some grocery shopping in the suburbs. The house was warm even on the coldest days and we found the beds really comfortable. The wifi was reliably fast and having access to Amazon Prime was a nice perk.

The Boston Presidential Penthouse Suite
I stayed here with a few friends it was great. Kraku was fast to respond to any questions, the area is quite walkable and easy to get downtown, snd the apartment was spotless!

In the heart of Jamaica Plain near Longwood
I enjoyed my stay very much! There were several good restaurants nearby and the whole area is very walkable. The path around Jamaica Pond was especially nice

E. Boston Condo| Airport, Downtown, Convention ctr
We had a great stay at Trevor's. The apartment is clean and comfortable and the kitchen seemed well stocked with cooking supplies. It is about an 8-10 minute walk to the Maverick T station. We were pleasantly surprised that even though the apartment is very close to the airport, there was no flight noise at all! In fact, the street was super quiet.
Pet-friendly condo rentals

Condo in downtown Boston
This was such a charming place in a wonderful location. Griffin and Carolyn were responsive and took really good care of us. They are great hosts who we highly recommend and would book with again!

A Cozy 3 Bedroom Home Close To Boston & Parking
Shirley's place is as described. It is comfortable and generous in size. There is parking available both in the driveway and on the street(with a supplied parking pass) for two cars altogether. Fresh linens are plentiful and the kitchen is very practical for cooking and eating in. Outdoor furniture on the back porch allowed us to invite over friends and socialize in nice weather. It is simple, but comfortable.

Nice Condo to Harvard, MIT, Fenway, with parking
We had a fantastic stay! It was an easy trip into Boston for our game at Fenway and doing all the tourist things near Boston Commons. Plus.....a parking space!! I would highly reccomend!

Family Home + Near Downtown + Cool Backyard!
We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.

#3A-Cambridge Walk to MIT+Harvard Amazing Location
We had a fantastic stay at Louisa’s beautiful place! The home was spotless, filled with great natural light, and equipped with everything we needed for a comfortable stay. The location was perfect—just a short walk to Harvard, making it incredibly convenient. Our time here was not only enjoyable but also highly productive, thanks to the peaceful atmosphere and charming surroundings of this lovely street. We will definitely be returning to Louisa’s amazing home, where we truly felt like we had a home away from home. A special thanks to Louisa and James for their hospitality and for making this trip so wonderful and unforgettable.

Right Near Convention Center and Train Station
We had a great stay at this South Boston condo! The location was perfect—just a short walk to the Convention Center, and the Seaport area, making getting around the city extremely simple. The space was spotless and clearly well cared for. Communication with the host was smooth and responsive throughout. The main bedroom was quiet and had a great work setup with a desk. The lower bunk bed is set directly on the floor, which actually worked out well—smaller adults in our group found it comfy and easy to sleep on. Parking was limited, but we found street parking without much trouble. Overall, a clean, convenient, and well-located spot—we’d definitely stay here again!

Spacious Dorchester Retreat | 2-bdrm condo
Wonderful host and wonderful place!! Would definitely come back!

Historic JP Brownstone with Parking. Pets Welcome!
Adorable brownstone in JP! Close to the orange line, quiet neighborhood with lots of families. House was great, lots of space.
Private condo rentals

Eastie near the airport Great location
Thank you for sharing your home! I found this a very convenient location to the T which brought us right to downtown Boston. I especially appreciated the umbrella that was left for use in the living room as I forgot mine and it was a rainy weekend. This apartment was spotless and I loved the espresso machine!

Beautiful, spacious South Boston Condo, Near T
Great location with good nearby access to Transit into Boston. Perfect a a few days stop.

Boston Townhouse - 3bd / 2.5ba - Central Location
Great spot for attending a convention - 20 minute walk. Neighborhood has groceries, banks, restaurants and a drug store. Host was very responsive and the place was super clean with everything we needed.

Stunning Victorian with Office | Mins to Downtown
Nice place to stay, convenient to all things Boston. 15-20 minutes to everything! Comfortable, nice TV, nice mattresses, and very responsive hosts. The water pressure in the shower is a bit low - something to be aware of if you have long hair to wash. Overall it’s a great place to stay and was the perfect fit for four people to spend a nice weekend exploring Boston. Thanks again.

Charming and Historic Apartment
This place is AMAZING! An absolute must stay. Close to public transit, restaurants, coffee shops, in the cutest neighborhood. We were in awe of how adorable and perfect and homey the apartment is. Truly one of my most favorite stays. The hosts were communicative and even let us drop our bags off early as we were coming from another air Bnb and didn’t want to lug our suitcases around Boston all day. I had some questions about check in and they responded to me in minutes. Truly wonderful.
Victorian Charm, Modern Style w/Private Entrance
Amazing peaceful getaway right around the corner from downtown Boston. A great location for walking and very easy to Uber to and from. Centrally situated and not too far from all the sites. Super clean home with everything my husband and sons needed. I especially enjoyed the back yard patio and all the natural sunlight in the living room and kitchen! We would definitely stay here again!

Sunny Apt w/ Baby Grand Piano Walk to Dining Spots
This is a great place. It is exactly as shown in pictures and spotlessly clean. Maria was pleasant, responsive and easy to work with. We paid for the parking spot which is right behind the house. I definitely recommend Maria’s places.

Magnificent Mansard Victorian Condo in Somerville
Very nice apartment with all amenities that are necessary for a long stay. I stayed for a month. The house is fully equipped. There are washing machine and dryer which are really helpful. The neighborhood is nice and quiet. Easy access to bus station and metro.There are many nice restaurants in the neighborhood of Somerville. Hamed, the host answered all my questions immediately and whenever there was a problem with the electric appliances he was always available to solve it. I would recommend this apartment definitely for long stay in Boston.
Destinations to explore
- Bed and breakfasts Middlesex County
- Rentals with a home theatre Middlesex County
- Rentals with a washing machine and dryer Middlesex County
- Beachfront rentals Middlesex County
- Apartment rentals Middlesex County
- Rentals with an EV charger Middlesex County
- Pet-friendly rentals Middlesex County
- Rentals with a kayak Middlesex County
- Rentals with a fire pit Middlesex County
- Private suite rentals Middlesex County
- Kid-friendly rentals Middlesex County
- Smoking-friendly rentals Middlesex County
- Cottage rentals Middlesex County
- Rentals with beach access Middlesex County
- Rentals with breakfast Middlesex County
- Rentals with pools Middlesex County
- Family-friendly rentals Middlesex County
- Rentals with lake access Middlesex County
- Rentals with a patio Middlesex County
- Waterfront rentals Middlesex County
- Rentals with an accessible height bed Middlesex County
- Rentals with a fireplace Middlesex County
- Townhouse rentals Middlesex County
- House rentals Middlesex County
- Guesthouse rentals Middlesex County
- Fitness-friendly rentals Middlesex County
- Loft rentals Middlesex County
- Rentals with a hot tub Middlesex County
- Rentals with outdoor seating Middlesex County
- Condo rentals Massachusetts
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Hampton Beach
- Boston Common
- Revere Beach
- Fenway Park
- TD Garden
- Harvard University
- Lynn Beach
- Duxbury Beach
- Brown University
- North Hampton Beach
- New England Aquarium
- Monadnock State Park
- Faneuil Hall Marketplace
- Freedom Trail
- Crane Beach
- Canobie Lake Park
- Roger Williams Park Zoo
- Prudential Center
- MIT Museum
- Good Harbor Beach
- Rye North Beach
- Museum of Fine Arts, Boston
- Quincy Market
- Bunker Hill Monument
- Things to do Middlesex County
- Food and drink Middlesex County
- Art and culture Middlesex County
- Sightseeing Middlesex County
- Things to do Massachusetts
- Nature and outdoors Massachusetts
- Art and culture Massachusetts
- Food and drink Massachusetts
- Tours Massachusetts
- Sightseeing Massachusetts
- Things to do United States
- Art and culture United States
- Tours United States
- Wellness United States
- Food and drink United States
- Nature and outdoors United States
- Entertainment United States
- Sports activities United States
- Sightseeing United States