Search Vacation Homes in Southeast Massachusetts

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

11 Rab. II - 13 Rab. II

In two weeks

18 Rab. II - 20 Rab. II

In one month

2 Jum. I - 4 Jum. I

In two months

30 Jum. I - 1 Jum. II

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."

SAR 1,182 total

includes taxes & fees

2 Apr - 3 Apr

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

SAR 2,229 total

includes taxes & fees

2 Apr - 3 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! "

SAR 1,694 total

includes taxes & fees

16 Apr - 17 Apr

"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!"

SAR 2,060 total

includes taxes & fees

3 Apr - 4 Apr

3 bedrooms, desk, iron/ironing board, WiFi

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

SAR 2,443 total

includes taxes & fees

8 Apr - 9 Apr

"The house was adorable - we loved it. "

SAR 1,684 total

includes taxes & fees

9 Apr - 10 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!"

"Absolutely gorgeous location with amazing views and lots of privacy in the winter. Will stay again!"

"Beautiful and comfortable space perfect for our family of four. "

SAR 1,030 total

includes taxes & fees

21 Apr - 22 Apr

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Southeast Massachusetts

"It's a nice property with great views. There are no indoor passageways to your rooms or to the pool. You have to go outdoors to get to them. It's kind of crazy that we got a kitchen area but they didn't have any solder pepper. It was well stocked with everything else to be able to cook but no seasonings. Everything else was wonderful. The beds were comfortable. Housekeeping kept us in towels."