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 condo rental, vacation lodging in Truro MA, Wellfleet cottages, or vacation beach rentals in Yarmouth.



Orleans Massachusetts Beach Rentals

Go to page 1 2 3 4 5 6 7 (1-15 of 131) Next Last
Sort by: Show rentals per page

Executive 11 room Luxury boat home on the water; Handicap access; Heated pool. — Property 164691

  • House
  • 7 bedrooms, sleeps 18
  • 6 bathrooms, 1 half bath
  • near the ocean, waterfront
  • swimming pool
Rates (shown in USD)
$1,250 - $1,350/night
$9,000 - $15,000/week

Perfect Summer Getaway — Property 116102

  • House
  • 3 bedrooms, sleeps 8
  • 2 bathrooms
  • beach, village
  • washing machine
Rates (shown in USD)
$210 - $225/night
$1,500 - $2,500/week
$1,400/month

Brand new 2+ bedroom townhome in East Orleans — Property 179760

  • Townhome
  • 2 bedrooms, sleeps 6
  • 2 bathrooms, 1 half bath
  • near the ocean, village
  • air-conditioning
Rates (shown in USD)
$1,900 - $2,200/week

Spacious, Private and Comfortable Waterfront Home — Property 180349

  • House
  • 3 bedrooms, sleeps 8
  • 3 bathrooms
  • near the ocean, waterfront
  • air-conditioning
Rates (shown in USD)
$1,800 - $2,800/week

Newly Furnished Classic Two-story Cape Rock Harbor — Property 319047

  • House
  • 3 bedrooms, sleeps 8
  • 2 bathrooms
  • near the ocean, town
  • air-conditioning
Rates (shown in USD)
$1,099 - $1,999/week

Enchanting Studio Boathouse Perched on Arey's Pond — Property 105217

  • Studio
  • studio, sleeps 2
  • 1 bathroom
  • near the ocean, waterfront
  • tennis
SPECIAL OFFER! Pre-Season Special June 1 - July 3

Ocean Front! Luxury Home! on Nauset Heights — Property 105227

  • House
  • 4 bedrooms, sleeps 10
  • 3 bathrooms, 1 half bath
  • near the ocean, waterfront
  • air-conditioning
Rates (shown in USD)
$700 - $750/night
$4,000 - $8,000/week
$16,000 - $17,000/month

Contemporary Post & Beam, Near State Park and Pond — Property 105224

  • House
  • 1 bedroom, sleeps 4
  • 1 bathroom
  • lake
  • washing machine
Rates (shown in USD)
$110/night
$725 - $925/week

Exquisite East Orleans Home — Property 141846

  • House
  • 4 bedrooms, sleeps 10
  • 2 bathrooms, 1 half bath
  • beach, village
  • washing machine
Rates (shown in USD)
$250/night
$1,800 - $2,400/week

New Custom Home--5 Acre Estate Setting--Shared Heated Pool — Property 173314

  • House
  • 3 bedrooms, sleeps 8
  • 2 bathrooms, 2 half baths
  • swimming pool
  • air-conditioning
Rates (shown in USD)
$2,500 - $4,200/week

Orleans - Nauset Beach is only one mile away - Large Deck and Yard ! — Property 163899

  • House
  • 2 bedrooms, sleeps 6
  • 1 bathroom
  • beach, village
  • air-conditioning
Rates (shown in USD)
$800 - $1,200/week
$1,000/month

Rock Harbor Retreat - architecturally designed with many details — Property 167182

  • House
  • 3 bedrooms, sleeps 6
  • 1 bathroom, 1 half bath
  • beach, village
  • washing machine
Rates (shown in USD)
$1,500/week

Private Mini-Estate with Main house, wonderful gardens and a pool — Property 152815

  • House
  • 4 bedrooms, sleeps 14
  • 3 bathrooms, 1 half bath
  • near the ocean, village
  • swimming pool
Rates (shown in USD)
$6,000 - $7,500/week

Romantic Pool-side Cottage on 5 Acre Estate Setting — Property 152047

  • Cottage
  • 1 bedroom, sleeps 3
  • 1 bathroom
  • near the ocean, rural
  • swimming pool
Rates (shown in USD)
$175/night
$900 - $1,400/week

Waterfront Estate with 300' Private Beach — Property 105234

  • Estate
  • 9 bedrooms, sleeps 19
  • 5 bathrooms, 1 half bath
  • beach, waterfront
  • washing machine
Rates (shown in USD)
$15,000/week
Go to page 1 2 3 4 5 6 7 (1-15 of 131) Next Last

Use of this Web site constitutes acceptance of the HomeAway.com Terms and Conditions and Privacy Policy.

© Copyright 2006-Present HomeAway.com, Inc. All rights reserved.