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Orleans Vacation Rentals(124)

124 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)
  • 4 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
1 Review
$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)
$1,125 - $2,286
per night
2 - 7 night minimum stay
  • 9 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 19
2 - 7 night minimum stay
(15)
$1,249 - $2,284
per night
2 - 7 night minimum stay
  • 4 BR,
  • 6 BA,
  • Sleeps 16
2 - 7 night minimum stay
1 Review
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 14
7 night minimum stay
(12)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
2 Reviews
$275 - $472
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
3 - 7 night minimum stay
(3)
$194 - $375
per night
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(6)
$600 - $800
per night
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
(4)
$600 - $943
per night
3 - 7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
3 - 7 night minimum stay
(3)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
(4)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night minimum stay
(5)
$1,240 - $2,720
per week
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
3 - 7 night minimum stay
(9)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 - 7 night minimum stay
2 Reviews
  • 5 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(4)
$1,600 - $2,400
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(8)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
(3)
$300 - $514
per night
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
(4)
$200 - $425
per night
2 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
2 Reviews
  • 5 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 11
1 Review
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 Reviews
$2,200 - $3,500
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
1 Review
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night minimum stay
(6)
$225 - $250
per night
2 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
2 - 7 night minimum stay
(9)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(19)
$700 - $1,795
per week
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 7
7 night minimum stay
(16)
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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

beautiful house with great location

5 of 5
We had a great time in Cape Cod. House was immaculate, included everything you would need, and was beautifully furnished. Great location convenient to all areas of the Cape, very close to beautiful beaches and terrific bike trails. Very highly recommended!
  • Submitted: Oct 11, 2014
  • Stayed: Sep 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