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Orleans 3,299 rentals
    •  
      $457 avg/night
      4 Bedrooms, Sleeps 12
      7
    •  
      $371 avg/night
      4 Bedrooms, Sleeps 8
      4
    •  
      $284 avg/night
      4 Bedrooms, Sleeps 10
      8
    •  
      $330 avg/night
      3 Bedrooms, Sleeps 6
      13
    •  
      $142 avg/night
      2 Bedrooms+, Sleeps 6
      8
      Frequently Booked
    •  
      $260 avg/night
      3 Bedrooms, Sleeps 6
      6
    •  
      $708 avg/night
      6 Bedrooms, Sleeps 12
      11
    •  
      $410 avg/night
      3 Bedrooms, Sleeps 7
      7
    •  
      $1,551 avg/night
      6 Bedrooms, Sleeps 16
      11
    •  
      $1,120 avg/night
      4 Bedrooms+, Sleeps 16
      10
    •  
      $719 avg/night
      4 Bedrooms+, Sleeps 14
      15
    •  
      $2,286 avg/night
      9 Bedrooms, Sleeps 19
      28
    •  
      $1,333 avg/night
      11 Bedrooms, Sleeps 24
      3
    •  
      $343 avg/night
      2 Bedrooms, Sleeps 6
    •  
      $843 avg/night
      4 Bedrooms+, Sleeps 8
      3
    •  
      $286 avg/night
      3 Bedrooms, Sleeps 6
      15
    •  
      $214 avg/night
      3 Bedrooms, Sleeps 6
      15
    •  
      $257 avg/night
      3 Bedrooms, Sleeps 9
      14
    •  
      $714 avg/night
      4 Bedrooms, Sleeps 8
    •  
      $200 avg/night
      2 Bedrooms+, Sleeps 8
      18
    •  
      View listing for price
      3 Bedrooms, Sleeps 8
      2
    •  
      $938 avg/night
      6 Bedrooms, Sleeps 16
      3
    •  
      $667 avg/night
      5 Bedrooms, Sleeps 10
      12
    •  
      $521 avg/night
      4 Bedrooms, Sleeps 8
      9
    •  
      $257 avg/night
      3 Bedrooms+, Sleeps 10
      38
    •  
      $343 avg/night
      3 Bedrooms, Sleeps 8
      5
    •  
      View listing for price
      2 Bedrooms+, Sleeps 6
      2
    •  
      $430 avg/night
      4 Bedrooms, Sleeps 8
      25
    •  
      $457 avg/night
      4 Bedrooms, Sleeps 8
      2
    •  
      $643 avg/night
      4 Bedrooms, Sleeps 8
      11
    •  
      $160 avg/night
      1 Bedroom, Sleeps 4
      16
    •  
      $714 avg/night
      5 Bedrooms, Sleeps 12
    •  
      $342 avg/night
      4 Bedrooms, Sleeps 8
      9
    •  
      $250 avg/night
      2 Bedrooms, Sleeps 4
      3
    •  
      $171 avg/night
      2 Bedrooms, Sleeps 4
      12
    •  
      View listing for price
      4 Bedrooms, Sleeps 9
    •  
      $350 avg/night
      4 Bedrooms, Sleeps 8
      1
    •  
      View listing for price
      3 Bedrooms, Sleeps 5
      22
    •  
      $400 avg/night
      4 Bedrooms+, Sleeps 10
      1
    •  
      $95 avg/night
      1 Bedroom, Sleeps 2
      2
    •  
      $249 avg/night
      3 Bedrooms+, Sleeps 8
      5
    •  
      $569 avg/night
      3 Bedrooms, Sleeps 8
      10
    •  
      $500 avg/night
      5 Bedrooms, Sleeps 12
      17
    •  
      $200 avg/night
      4 Bedrooms, Sleeps 10
      5
    •  
      $600 avg/night
      5 Bedrooms+, Sleeps 12
      3
    •  
      $301 avg/night
      3 Bedrooms, Sleeps 6
      1
    •  
      $430 avg/night
      5 Bedrooms, Sleeps 11
      6
    •  
      $500 avg/night
      5 Bedrooms, Sleeps 9
      4
    •  
      $357 avg/night
      3 Bedrooms, Sleeps 12
      3
    •  
      $243 avg/night
      4 Bedrooms, Sleeps 8
      2

Recent Orleans reviews

  • Just a fabulous place!

    Rebecca J.

    "We love this little cottage. We have stayed here twice with our 2 dogs. The location is exceptional. You're within walking distance of shops and restaurants and the bike trail. Plus the view from the front porch is fabulous. The best part is the bakery right outside your back door!! National seashore is 15 minutes away. The cottage itself is just comfortable for 3 grown-ups. The kitchen has everything you need and a nice supply of puzzles and games and books. Very clean bathroom and bedrooms as well. The owner, Kathie, is very personable and wants to make sure your visit is just right."
    • Stayed December 2016
    • Submitted January 8, 2017
    • Source VRBO
    View this listing
  • Our Most Favorite Vacation Spot

    Fran

    "We feel lucky to have discovered Molly's cozy little cottage a few years ago on VRBO. This is our third year there for a couple of weeks in September. We surely hope to return again next year. Pleasant Bay is stunningly beautiful, my very favorite place for kayaking at all tidal conditions. Our kayaks are kept snugly upon the bank of the Namequoit River, just a short walk away from the cottage. From there, we can paddle in all directions in Pleasant Bay as well up the river to Arey's Pond! And also from the cottage, it's just a 15 min. cycle to reach the Cape Cod Rails to Trails in the center of Orleans. Stop on your way back at a delightful little garden stand on Monument Rd. to enjoy local vegetables and fruit. We spent our honeymoon in Orleans, 51 years ago and have been coming back ever since because nothing for us compares to the beauty of this area."
    • Stayed September 2016
    • Submitted September 30, 2016
    • Source VRBO
    View this listing
  • Great house

    Vincent G.

    "The house was super close to the best beach in brewster, Crosby lane."
    • Stayed August 2016
    • Submitted August 28, 2016
    • Source HomeAway Family
    View this listing
  • Home away from home

    Diane F.

    "The Friendship House is a home away from home. Spacious, clean and cozy, with a great kitchen (fully stocked!) for home-cooked meals enjoyed on the deck with an ocean view!! Minutes walk/run to the beach, outdoor shower (my son's favorite and always a treat) and an owner who couldn't be more friendly and helpful- always willing to chat up the best spots (and cupcakes) in town! I am getting home-sick for it as I write. Spent our 3rd vacation this past June and am thinking a week is not enough. Was truly sad to leave :(, but am looking forward to next visit :). A deal and a half :). ~ Connor and Diane"
    • Stayed June 2016
    • Submitted August 2, 2016
    • Source VRBO
    View this listing