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Check prices for these dates

Next weekend

21 Rab. I - 23 Rab. I

In two weeks

28 Rab. I - 30 Rab. I

In one month

11 Rab. II - 13 Rab. II

In two months

9 Jum. I - 11 Jum. I

Compare 425 Vacation Homes in Chestnut Hill with updated reviews, rates, and availability.

"The Quiet Single Family House was the perfect place to stay for our group of a mom and 3 college-aged girls. We had plenty of space, the home was very clean and comfortable, and we were central to everything we wanted to do in the area. The neighborhood was peaceful and it wasn’t far to restaurants and grocery stores. The homeowner was a great source of information on things to do in the area as well as very responsive to any questions I had. I’d definitely rent from her again. We had a...

"Nice neighborhood. My only concern was there are a lot of stairs.Great location close to everything, Good restaurants close by. Had a wonderful time. "

"Really enjoyed the house. Great location, easy checking in. They even had a decorated Christmas tree for us."

"My family and I had a wonderful stay at Luxury Bayside Jewel in Squantum, MA, over the holidays, and I cannot recommend this property enough. From the start, the property manager, Susan, made the experience seamless. She was incredibly responsive to all my questions before and during the trip, addressing even the smallest details—like when and where to put the trash out—with patience and care.The home itself exceeded all expectations. Thoughtful touches made us feel welcome from the moment we...

"Excellent property; easy to work with owners."

SAR 1,821 total

includes taxes & fees

11 Mar - 12 Mar

"We had a wonderful stay. The apartment was exactly as advertised. It’s very clean and in a cute borough with some great restaurants and shops and any other convenience you might need. The apartment has a large kitchen that’s great for cooking your own meals if you wish to do so. Check in was completely seamless even though we were arriving late at night. "

SAR 1,466 total

includes taxes & fees

11 Mar - 12 Mar

"We had a pleasant stay. The house is cozy, clean and comfortable. It is in a convenient location with several restaurants in walking distance as well as a supermarket. The neighborhood is quiet with little traffic coming through. Victor the host was responsive and answered any questions we had. Would recommend without hesitation."

"Place was great and host linda was very accommodating "

"Everything was as expected. Convenient location. Would recommend."

3 bedrooms, desk, iron/ironing board, free WiFi

"Thank you for sharing your wonderful house to us. "

SAR 1,873 total

includes taxes & fees

11 Mar - 12 Mar

"Beautiful home, spacious, clean, warm, and cozy. Enough space for a family of 5. The neighborhood was easy to find and navigate. The mattresses were not as supportive as we’re used to but we didn’t go to Boston/Chelsea to sleep. The shower was excellent. The owner lives close by which came in handy when the smoke detectors went off on our first night and we couldn’t figure out why. He was prompt in making sure we were safe and the house wasn’t burning and then proceeded to take care of the...

"Great stay, communication was amazing "

SAR 1,634 total

includes taxes & fees

11 Mar - 12 Mar

"We’re a band from Jersey. We play at Ned Devines and The Harp in Boston a few times a year. As a band, budgeting is crucial. Housing 4 people can be super expensive. This property has a great price point allowing some money left over in the budget to buy groceries at a close by grocery store. We were able to check in, go to the gym together, grocery shop, and relax, all before heading to the venue to check in. Finding a place with a clean safe neighborhood for parking our vehicles and feeling...

"This is a really great apartment in a very convenient location, Cherie was a very attentive host and really we couldn’t have asked for better accommodation for our needs as a family. Thank you."

SAR 1,693 total

includes taxes & fees

11 Mar - 12 Mar

Fridge, microwave, coffee/tea maker, toaster

"We had a fabulous time staying in this lovely brownstone. The location was perfect, responsiveness from the host was perfect, and so were the amenities, layout, and accessibility. We would definitely return again."

"This was a convenient pick for us, being only about 1.5 miles from other family members home. We didn't spend much time there but it was very comfortable. The weather got very cold for a few days, below freezing and we had no hot water upstairs. I contacted management and they had someone out within hours, ON A SUNDAY and started addressing the problem. I would stay here again."

SAR 2,243 total

includes taxes & fees

11 Mar - 12 Mar

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Other property types in Chestnut Hill

"Know that this is a typical small Boston room. There is no dresser. The microwave is in the hall and there is no parking. However, the shower and the toiletries provided are great! Overall, if you can get past the size of the room this hotel is really nice. Make sure to get coffee and pastries from the French bakery next door. "

SAR 944 total

includes taxes & fees

22 Mar - 23 Mar