Apartment holiday rentals in Wellesley

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Popular amenities for Wellesley apartment rentals

Weekly apartment rentals

Top Guest favourite
Apartment in Salem
4.98 out of 5 average rating, 385 reviews

Winter Island Retreat

JaniceRating, 5 stars2 weeks ago
Look no more! Winter Island Retreat is a seaside oasis that creates an atmosphere of tranquility and peace. From the moment I arrived I was struck by it's beauty captivated by the stunning sunrises to start each day The retreat is charming and a place of solace. The beautifully manicured lawn and gardens filled with lush floral designs adds to its magic. while the front porch with its rocking chairs, invite you to slow down and savor your morning coffee or lose yourself in a good book. Evenings are equally special walking the path to the beach and settling into the adriondack chair with a glass of wine It's a peaceful ritual that grounds you in gratitude. The home itself is cozy, comfortable and thoughtfully decorated with calming beachy touches that make you feel at ease. It's perfectly located just minutes from downtown Salem. I'm grateful to be one of the lucky guests to stay in David's home. He was a kind and gracious host. A truly memorable retreat I will be back
Guest favourite
Apartment in Watertown
4.96 out of 5 average rating, 27 reviews

Brand New, Beautiful 2 BR Townhouse w/Parking!

RRating, 5 stars2 weeks ago
clean and well stocked and well maintained unit; plus Domenic was accessible and communicative throughout the stay; the unit was a great staging area for trips around the Boston area; the unit could benefit from the addition of a few baking pans (we couldn’t find any) and also the AC units in the bedrooms need upgrading (they were loud and inefficient) which I understand is in progress; the cost was reasonable compared to Boston hotel prices; overall it was comfortable and fell light a home away from home
Superhost
Apartment in Norwood
4.78 out of 5 average rating, 60 reviews

The Plant Haus

MagdalyneRating, 5 stars2 days ago
This was our second time staying in Quontay’s home, and, like the first time, we loved our stay! Her home is beautiful and clean, with beautiful plants and paintings everywhere. The vibes are immaculate. It was the perfect place to stay for our night out in Canton. We highly recommend!!
Top Guest favourite
Apartment in Waltham
4.96 out of 5 average rating, 77 reviews

Just Renovated, Private & Quiet 2 Bedroom Unit

BrittanyRating, 5 stars2 weeks ago
Loved Heidi’s place. So cute. Just as described and just like home! Check in was a bit difficult though because it was dark and it was hard to find the number of the houses. Other than that, I love everything about this place. So cozy. Heidi was also nice enough to give us some restaurant recs and was very communicative the entire stay.
Top Guest favourite
Apartment in Newtonville
5 out of 5 average rating, 31 reviews

Apartment in Newton, MA

VictoriaRating, 5 starstoday
Grey and Leslie’s place was perfect for my fiancé and I while visiting Boston! It was very easy to get to the commuter rail, which we rode to get to a Red Sox game. Grey and Leslie gave great suggestions and were very responsive when I had any questions. Highly recommend!
Top Guest favourite
Apartment in West Roxbury
4.92 out of 5 average rating, 96 reviews

Sleeps 4, comfortable apt. in quiet Boston suburb

MikeRating, 5 stars2 weeks ago
We had an absolutely fantastic stay at Sophie and Gal’s beautiful Boston apartment! The apartment was spacious, filled with natural light, and felt like a true home away from home. The apartment was impeccably clean, with every amenity you could need – from a full kitchen and cozy living room, flat-screen TV, and an awesome shower that, as a taller family, we loved. The location is unbeatable! Just a short drive to Downtown Boston and Boston College, with easy access to free street parking, which made getting around stress-free. The neighborhood itself is quiet and family-friendly; perfect for a relaxing stay after a day of exploring. We loved the private entrance to the second-floor apartment in this charming home. It provided a sense of security and privacy that made our visit even more comfortable. Sophie and Gal were exceptional hosts – always responsive and accommodating, ready to help with any questions we had. Their attention to detail and hospitality made our stay amazing!
Guest favourite
Apartment in West Roxbury
4.92 out of 5 average rating, 37 reviews

Cozy 2-Bedroom Apartment Near Dedham Legacy

MaryRuthRating, 5 stars4 days ago
Was a great place for a 1 night stay! Will definitely look to book again in the future.
Superhost
Apartment in Norwood
4.76 out of 5 average rating, 54 reviews

Great hotel alternative.Close to Boston

TheodoreRating, 5 stars4 months ago
One of the nicest and warmest Airbnb’s I have been to in a while. Comfy bed, full kitchen, warm and comfortable with old style radiators that made very cozy on a cold night. Thank you. Will plan to come back when available.

Private apartment rentals

Top Guest favourite
Apartment in Cambridge
4.97 out of 5 average rating, 339 reviews

Picture-perfect Cambridge guest apartment, parking

JillRating, 5 stars2 days ago
Steve and Nancy were wonderful, gracious hosts. They allowed us to check-in early, gave great information about the area, and were awesome communicators from the time we booked until we checked out. The apartment was perfect for my nephew and me. It was a restful place to return after long days of sightseeing and lots of walking!
Superhost
Apartment in Newton
4.79 out of 5 average rating, 39 reviews

Comfortable two bedroom in Newton

CristinaRating, 5 stars1 month ago
Our family stayed 2 nights, and we enjoyed our stay (we'd definitely stay again). The house was easy to find with off street parking. It was clean and spacious. You're about .7 from the commuter train, and the area was cute. We're runners and you could jump on the Charles River path about 1/3 mile away. There is no AC in the house, and there was a heat wave on our first night. The upstairs was pretty stuffy and warm, and since it was April, they didn't have the ACs/fans in the window yet. I reached out to see if they had any fans and they replied right away, and dropped off some fans. Once we had the window fan in, the upstairs cooled down. We appreciated their quick response and we slept well.
Top Guest favourite
Apartment in West Roxbury
4.96 out of 5 average rating, 24 reviews

Cozy studio near-Train&Bus, safe area in Boston

HollyRating, 5 stars1 week ago
Margarita is a friendly and responsive host. Her place was just like the pictures-so cute. I liked everything about the place. It was an easy walk to Center St. where there were shops and restaurants. Bus stops and commuter train were within walking distance for access to downtown Boston. The living space was nicely appointed. Everything was very clean and well supplied with toiletries. I would stay there again so definitely give it a high recommendation.
Guest favourite
Apartment in Arlington
4.95 out of 5 average rating, 21 reviews

Cute Accessible Studio: No stairs, W/D, Parking

AlyssaRating, 5 stars2 days ago
Great location close to Arlington Heights' downtown and public transportation. Loved listening to the nearby brook and visiting the little pocket park right next to the house. Beautiful neighborhood (especially this time of year). There was some construction happening near by that had us waking up to jackhammers one morning, but that was short lived and situational. It was great to be able to walk the Minuteman Bike/Walking trail and have so many amenities close by. Even though there are several units in the house, we were only minimally aware of the presence of other guests.
Superhost
Apartment in Ashland
4.64 out of 5 average rating, 11 reviews

Studio in Ashland Massachussets

JosephRating, 5 stars1 month ago
this little studio was absolutely perfect. it have everything we needed & more. there was plenty of linens, pillows, and comfy sleeping quarters. I would stay there any time I was in town. Talita was responsive every time I sent a message. easy in & easy out. beautiful little place.
Guest favourite
Apartment in Westford
4.93 out of 5 average rating, 90 reviews

Large One Bedroom Apartment

MaraRating, 5 stars1 day ago
I had a great experience with our stay. It was spacious and a perfect getaway. Would definitely stay again or recommend to anyone I know.
Superhost
Apartment in Watertown
4.78 out of 5 average rating, 68 reviews

Entire, Spacious, Cozy Apartment, Private entrance

AliceRating, 5 stars4 weeks ago
Very clean and spacious one bedroom. Hugely helpful to have on-site parking! A very nice kitchen space. Helpful instructions on the fridge once you get inside. Loved ‘The Diner’ which was an easy and pleasant walk.
Guest favourite
Apartment in Everett
5 out of 5 average rating, 19 reviews

Elegant Oasis with Pool and Gym

HoaRating, 5 stars2 days ago
We had such a great stay! The place is super modern, clean, and feels brand new. It had all the little touches and amenities that made our trip really comfortable. Our family really enjoyed it — it felt like a home away from home. We’d definitely stay here again!

Apartment rentals with a hot tub

Superhost
Apartment in Derry
4.82 out of 5 average rating, 496 reviews

The Loft Escape Apartment

IanRating, 5 stars3 weeks ago
If I could give 4.5 stars I would. Evan and Rachel were wonderful, responsive hosts and the property was exactly what I hoped for. Upon arrival, the washer looked and smelled very moldy. My advice to any future guests would be to please consider airing out the washer after using it to help prevent this. The AC/heat pump units also seemed a bit musty. However, after communicating the issue to the hosts, they quickly offered to come in later that day to sanitize the washer and give our unit an ozone treatment to deal with the mold spores in the air. I really appreciated the effort and it resolved the problem enough for me to feel comfortable washing my clothes. The convenience of living on the main road in town was nice, but the street was a bit noisy at night. Nevertheless, I would definitely stay at The Loft Escape Apartment again!
Guest favourite
Apartment in Woburn
4.94 out of 5 average rating, 152 reviews

Your Cozy 1 BR Apt & Relaxing Retreat

VivianaRating, 5 stars1 week ago
We had a fantastic stay at this place! The house was spotless, with a fully stocked kitchen and bathroom that made everything super convenient. Thiago was incredibly helpful, attentive, and kind throughout our stay, which made the experience even better. We especially loved the jacuzzi area and the large, comfy couch in the living room. The entire place offered great privacy. Would definitely recommend it!
Superhost
Apartment in Federal Hill
4.8 out of 5 average rating, 25 reviews

Large Studio Apt off Fed Hill

RosaleeRating, 5 stars3 weeks ago
Stayed for 3 nights to visit family. Was a great stay! Tub is beautiful and comfy. Takes a while to fill as mentioned in description but stays warm! No complaints. Would book again on my next trip!
Top Guest favourite
Apartment in Winthrop
4.96 out of 5 average rating, 243 reviews

Oceanfront Pool. Close to Boston. Free Parking.

LillianRating, 5 starstoday
This place was great! Conveniently located outside the city close to many T stations. The hosts were proactive communicators and very helpful! Beach access, hot tub, pool, local shops, it was the perfect spot for a getaway.
Guest favourite
Apartment in Arlington
4.98 out of 5 average rating, 194 reviews

Lakeside apartment, patio, hot tub, outside shower

ParkerRating, 5 stars1 month ago
We had the best time in Arlington this past week! We came for the Boston marathon. The place was beautiful and the location was perfect. It was close to Boston but far enough out for the peace and quiet. Doug and Hope were the most exceptional hosts. They were accommodating and very responsive. They went above and beyond to make our stay and everything we needed as easy as possible. They were so great and we hope to come back in the future!!
Superhost
Apartment in Derry
4.77 out of 5 average rating, 381 reviews

The Hideaway Studio Apartment

IanRating, 5 stars2 weeks ago
I stayed with Evan and Rachel previously in the apartment located upstairs from the Hideaway Studio. Once again, I was not disappointed! Spotlessly clean, great location, clear instructions, and perfect for a single guy looking to stay a few nights in Derry. No complaints except I was unable to find any dish soap, so I had to wash everything with hand soap. Also, when using the hot tub, I was bothered by a musty smell coming from the water, especially when all the jets were turned on. Perhaps I’m just overly sensitive to mold. Also, some of the pictures should be updated. While I didn’t need it for my stay, the bunk bed was not set up, so it was just the full bed with the twin trundle underneath. Wonderful stay overall, and I would not hesitate to book this location again!
Top Guest favourite
Apartment in North End
5 out of 5 average rating, 45 reviews

Amazing Location in Little Italy with Roof Deck

NancyRating, 5 stars1 month ago
Beautiful condo, perfect for 2 people! Everything you need was provided. Deck was lovely. The location can’t be beat. Highly recommend for a Fun Boston Experience!
Superhost
Apartment in Cambridge
4.8 out of 5 average rating, 123 reviews

Studio Apt private bath+ Hot Tub, free parking

ChristopherRating, 5 stars3 days ago
Annique's place is a second floor flat in a quiet street not far from the "T" and grocery stores. The flat has a beautiful wooden floor and spacious bathroom. For me, the high point was having an office space with a standing desk - I loved it! The amenities Annique provides shows she is an extremely thoughtful host and is very responsive. Definitely an excellent place to stay..

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