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Orleans Waterfront Vacation Rentals Vacation Rentals(46)

46 Results
$3,150 - $12,400
per week
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 13
7 night minimum stay
(7)
$999 - $2,500
per night
2 - 7 night minimum stay
  • 6 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 16
2 - 7 night minimum stay
(4)
$1,249 - $2,284
per night
2 - 7 night minimum stay
  • 4 BR,
  • 6 BA,
  • Sleeps 16
2 - 7 night minimum stay
1 Review
$1,125 - $2,286
per night
2 - 7 night minimum stay
  • 9 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 19
2 - 7 night minimum stay
(15)
$275 - $472
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
3 - 7 night minimum stay
(3)
  • 5 BR,
  • Sleeps 11
$600 - $943
per night
3 - 7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
3 - 7 night minimum stay
(3)
  • 5 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(4)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
1 Review
$2,000 - $2,429
per night
2 - 7 night minimum stay
  • 11 BR,
  • 7 BA,
  • 1 HF BA,
  • Sleeps 22
2 - 7 night minimum stay
(3)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
(4)
  • 5 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
(6)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
7 night minimum stay
1 Review
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
1 Review
  • 10 BR,
  • 6 BA,
  • Sleeps 19
(5)
  • 6 BR,
  • 4 BA,
  • 3 HF BA,
  • Sleeps 16
  • 3 BR,
  • 2 BA,
  • Sleeps 8
5 - 7 night minimum stay
(4)
$300 - $557
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
(8)
$300 - $557
per night
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 12
3 - 7 night minimum stay
(13)
$280
per night
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
1 Review
$2,700 - $3,750
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
$4,000
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(9)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
$8,000
per week
7 night minimum stay
  • 6 BR,
  • 3 BA,
  • Sleeps 12
7 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 6
$798 - $896
per week
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
7 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 6
$3,500
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
$2,500 - $3,300
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
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Recent Orleans Reviews

Fantastic home on Cape Cod

5 of 5
Having just spent a week in this lovely home, celebrating a milestone birthday with college girlfriends, I cannot say enough about this fabulous property. The home is immaculate and contains every luxury convenience one could wish for. Spacious bedrooms with fantastic views over the marsh to the ocean, huge deck to enjoy both the sunrise and sunset and everything in between, wonderful kitchen with every appliance one could dream of including a vitamix blender so that we could counteract the lobster rolls and clam chowder (best ever provided by the home owners!) with a healthy smoothie, heated pool with a waterfall (which the owners increased the temperature on to accommodate us southern ladies of a certain age), luxury bed linens and big fluffy towels, and a state of the art sound system. Far too many amenities to list, but suffice it to say it was not easy to pry ourselves out of the house to explore the rest of the Cape. The owners provided superb guidance tho on things to do and see as well as detailed dining options. The location was close to many activities and restaurants altho I must say that simply enjoying the Briar Point house and grounds was at the top of our list of favorite things to do. The sounds of nature including many birds during the day and owls at night was topped off by a sighting of a mother fox and three kits on our last day. I would love to return to this beautiful setting with my family and can recommend this luxury home with absolutely no reservations . Simply a wonderful place to spend time with friends or family!
  • Submitted: Oct 12, 2014
  • Stayed: Oct 2014

Unforgettable Wedding Location!

5 of 5
Although my fiancé and I are not from Cape Cod, we knew as soon as we got engaged that the Cape was the perfect destination for our wedding. Despite residing in Chicago we researched from afar and narrowed our selection to 10 different venues/locations to visit the following month. Although we saw some amazing places, we knew in our heart the winner would be the Winslow Estate and upon arriving for our tour and driving up the entrance way, our decision was instantly made even before we got out of the car. Our criteria was simple: we wanted our ceremony and reception at the same location, preferably outside, where our wedding party was also able to stay through the weekend and the Winslow Estate accommodated all the above. To say the estate is beautiful is a complete understatement. The house itself, the yard, the views of Pleasant Bay are all breathtaking. Although I’ll admit the price was a bit of a surprise at first, we can say now it was 100% worth it. Once we decided that the Winslow Estate was right for us, the owners (Ken and Ginger) were incredibly helpful, responsive and supportive throughout the entire planning process; always available to answer questions via phone or e-mail or provide recommendations as needed. Given that we were planning a wedding from Chicago, this level of support was certainly needed! We were able to have ourselves and our entire wedding party sleep and stay at the estate leading up to the wedding. We had a smaller guest count (around 85) that all fit comfortably during both the ceremony on one side of the yard and then under a covered tent during the reception on the other side. I’d recommend the Winslow Estate to anyone without hesitation whether for weddings, family reunions, etc. Our memories from our wedding day are priceless, largely due to the location we held it at. Thank you Ken and Ginger for an amazing experience!
  • Submitted: Oct 6, 2014
  • Stayed: Sep 2014

We WILL be back!!!!

5 of 5
If you're on the fence about whether to rent the Bay House, I am here to tell you that the pictures don't do it justice. My family and friends (party of 9) arrived for a birthday celebration weekend and were awe-struck as we drove down the driveway towards this beautiful destination. The minute you arrive, you know you're in for something special. The bay can be seen through the glass front door, giving you just a hint of what awaits. The cottage-type furnishings and farmhouse dining room table are warm and inviting and yet, casually elegant. We were greeted by fresh flowers on the table and in the front hallway. We treated ourselves to dinner on the back deck while watching the sun set and the moon rise over the water. Everyone loved this house with its private beach and scenic views so much that we hated to leave. One word...BEAUTIFUL! Thank you Ken and Ginger, for a wonderful weekend and amazing memories! We WILL be back! Cathy T
  • Submitted: Sep 8, 2014
  • Stayed: Sep 2014