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Compare 795 Vacation Homes in Southeast Massachusetts with updated reviews, rates, and availability.

"This property is absolutely beautiful, the ocean view is spectacular sunrise and sunset is breathtaking. Thank you Mike and Judy for making our stay possible."

AED 1,157 total

includes taxes & fees

31 Mar - 1 Apr

"The house was just as described. Beautiful, comfortable and it had everything we could possibly need. Peaceful, quiet, and a very convenient location."

AED 9,535 total

includes taxes & fees

31 Mar - 1 Apr

"Beautiful home! Check in was easy. I had a quick question and the host answered very promptly and was super nice ! House was very clean and the electric fireplace was a plus! We will definitely stay here again! "

"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...

"House was just as it looked in pictures. Great yard and hot tub. Close to all the cape has to offer. Will stay again !"

"Hope to be back soon!"

AED 1,817 total

includes taxes & fees

31 Mar - 1 Apr

3 bedrooms, desk, iron/ironing board, WiFi

"Great house, all redone, great location. Right at the edge of town but quiet area. "

AED 2,392 total

includes taxes & fees

6 Apr - 7 Apr

"The house was adorable - we loved it. "

AED 1,768 total

includes taxes & fees

3 Apr - 4 Apr

"We plan to come back. This was a great place for 3 couples. We had a little problem with bugs but nothing we couldn’t handle. Close to the bay and everything we wanted. Definitely a good experience. Recommend"

"Host was always responsive. Property was even better than listing pictures. Location cannot be beat. The perfect gathering place for our Fall Friends Getaway. Already booked for next year! "

"I had a great Labor Day weekend here with my family. The house was very clean and very close to Nauset Light Beach. I would definitely stay here again."

"Perfect for our stay, comfortable beds, well stocked kitchen very clean, easy to communicate with owner, nice that it is pet friendly"

"We had a wonderful time. The home is clean, comfortable, well furnished, and extremely well stocked. Plenty of dish detergent, paper towels, soap, etc. and they even provided travel size containers of shampoo and conditioner. Great location within walking distance to the beach. Would definitely stay here again."

"We enjoy it all. "

"Location was great for us. Beds were very clean and comfortable and many bedrooms. Kitchen view was amazing and appliances worked well. Overall, very nice, quiet vacation home. "

"We thoroughly enjoyed our stay! The house is lovely! An easy walk to downtown shops and restaurants and a beautiful neighborhood as well! Lisa and Brian are wonderful hosts and are available with anything you may need. A true gem for your Chatham stay!"