Old-Fashioned Fun in Orleans

Orleans Vacation Rentals, Orleans Apartments, Condos, Cottages, Studios, Townhomes, Houses & Estates



Orleans, Massachusetts, once a quaint fishing and whaling village, has evolved into one of the most welcoming resort towns on the East Coast. It’s no wonder Northeasterners flock to vacation there, year after year. For your next vacation, why not experience Orleans, Cape Cod like a local and stay in an Orleans vacation rental with your group? Homes range from slick apartments to waterfront estates and complement most itineraries. Travel alone or bring the family – either way you’re sure to have a relaxing time in an easy-paced setting.

Plan a fishing vacation on the Cape during the warmer months. Reserve a waterfront cottage on Pilgrim Lake with its own dock and boat slip. Grill what you catch at home and have plenty of money left over to spend at the local antique stores and crafts shops in town. Or consider a golfing vacation in Orleans. Round up your most swingin’ buddies and chip in on a modern townhome located on the green of an executive golf course. Practice your line drive during the day, then at night, watch the pros do it better on your rental’s 50" TV screen.

Orleans is a great place to soak up some New England culture. Catch the Pops in the Park during the summer, a free annual show that locals look forward to all year. Or take the kids to the French Cable Museum for an educational experience they’ll think is fun. Ride bicycles on the famous Cape Cod Rail Trail for another perspective of beautiful Cape Cod, the settle back at your vacation home for a relaxing night in front of a cozy fire. You’ll soon discover that those in the know prefer staying in Orleans vacation homes, so book now!

There are additional vacation properties that the Cape Cod peninsula has to offer. To increase your search selection of Cape Cod vacation rentals consider checking out following rental options: Dennis MA vacation rentals, Bourne area vacation homes, Chatham homes, Eastham beach rentals, lodging in Falmouth MA, Harwich rentals, Provincetown lodging, vacation lodging in Truro MA, Wellfleet cottages, or vacation beach rentals in Yarmouth.

Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Cabins
Chalets
Cottages
Estates
Homes
Barns
Boats
Bungalows
Castles
Condos
Farmhouses
Hotels
Lodges
Studios
Townhomes
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Orleans: Houses, Cottages & More(286)

286 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
$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)
$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
  • 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
  • 4 BR,
  • 2 BA,
  • Sleeps 9
7 night minimum stay
$1,299 - $1,799
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
7 night minimum stay
$275 - $472
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
3 - 7 night minimum stay
(3)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
  • 5 BR,
  • Sleeps 11
$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)
  • 5 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 - 7 night minimum stay
2 Reviews
$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)
$325
per night
3 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night minimum stay
$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)
$3,000 - $3,975
per week
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
Advertisement