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Vacation Rentals in Orleans, Massachusetts

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about Orleans

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Orleans, Massachusetts vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Orleans are added and updated every week!

Compared to hotels, Orleans vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Orleans, Massachusetts Vacation Rentals and Tourism

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Orleans things to do

 

Nauset Beach

Nauset Beach has HUGE waves! You can't boogie board there because they crash onto the shore. They have a clam shack that sells overpriced shirts and...read more

 

Wequassett Resort and Golf Club

Hands down, best resort my family has ever been to. Never met a staff quite like this. We were celebrating three birthdays, and they made sure every single...read more

 

Nickerson State Park

I have been camping at Nickerson for years, it is my favorite place to camp on the Cape. Awesome campsites, and only $15/night. It's a state park so the...read more

 

Nauset Light Beach

This beach is decent with ample parking. We visited in the evening so there wasn't an entrance fee. The view was quite nice and the restroom was clean....read more

 

Marconi Beach

HUGE waves for this area. Great for surfing. Smooth sand, not too rocky. Clean, clear water. Note that there's no concession stand. Not a problem for me,...read more

 

Yankee Ingenuity

In a sea of tourist artsy stores with all the same jewerly and art, Yankee Ingenuity brings you back to what a catch all store should be. There a little bit...read more

 

Arnold's Restaurant

Cash only! In an attempt to maximize their profits by reducing credit card fees, Arnold's does not accept credit. They do have an ATM for your...read more

 

Orleans Bowling Center

Awesome BBQ with a Big Lebowski atmosphere. Had the rack of ribs. Dry rub. They offer three sauces: sweet, vinegar based, and chipotle. The ribs were meaty...read more

 

Wellfleet Drive-In Theatre Flea Market

I went to a drive-in!!!! Do you know how long I've wanted to go to a drive-in!?!??! The experience at the Wellfleet drive-in was delightful. There is no...read more

 

Skaket Beach

Skaket Beach is a great beach! You can swim at high tide and walk far out through tide pools and look for crabs at low tide. They have bathrooms and a...read more

 

Coast Guard Beach

This beach is hideous. It smells foul too. The general public isn't even allowed to go here for some reason. Skip it.read more

 

Idle Times Bike Shop Inc

Very nice store with attentive and polite staff. Stocked to manage all of your cycling needs.read more

 

Goose Hummock Shop

a very good bait and tackle shop decent prices friendly people i do like to fish alot when im down the cape i always try to stop there at least onceread more

 

The Little Capistrano Bike Shop

Great bikes, lovely people! We got vouchers for free rental from a living social when we booked our rooms at the Town Crier. Service was perfect and the...read more

 

Orleans Cycle

This shop has quality rentals, a decent assortment of accessories, experienced mechanics, and a "can't be beat" location right on the CCTR in the center of...read more

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Breathtaking Orleans Marshfront and Ocean View Estate
Orleans House Rental Picture
  • bedrooms 5
  • community Mallard Lane
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $600 - $700 /nt
    $4,200 - $4,900 /wk
 
 
 
 
 

6 reviews write a review

Town Cove Waterfront Home
Orleans House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $5,495 /wk
 
 
 
 
 

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Water views and access! Gorgeous 3 BR home
Orleans House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 8
  • baths 1
  • rates (USD) $250 - $430 /nt
    $1,500 - $2,900 /wk
 
 
 
 
 

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Close to Nauset & Skaket Beaches, Walk to Firebirds Game
Orleans House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $195 - $271 /nt
    $1,900 /wk
    $7,500 /mth
 
 
 
 
 

6 reviews write a review

Beautiful Home in Brewster Right Near Beaches
Orleans House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $250 - $411 /nt
    $2,375 - $2,875 /wk
 
 
 
 
 

1 reviews write a review

STILL AVAILABLE - SEPT 2ND AND 3RD WEEK!!!
Orleans House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths
  • rates (USD) $700 - $1,795 /wk
 
 
 
 
 

14 reviews write a review

Skaket Beach--At it's Best--Central AC--Walk to the Beach
Orleans House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $1,700 - $2,300 /wk
 
 
 
 
 

8 reviews write a review

Spacious And Family Friendly, Walking Distance To Fresh Water Beach
Orleans House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,400 - $1,500 /wk
 
 
 
 
 

1 reviews write a review

Private, Spacious Home A Short Walk Down Private Path to Skaket Beach
Orleans House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,400 - $2,100 /wk
 
 
 
 
 

10 reviews write a review

Charming Post & Beam Near State Park and Pond
Orleans House Rental Picture
  • bedrooms 1
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $125 - $143 /nt
    $750 - $1,000 /wk
 
 
 
 
 

6 reviews write a review

This Cape Cod charmer is totally redone and is a quick stroll to Skaket Beach
Orleans House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $3,500 /wk
 
 
 
 
 

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New listing - view of Nauset Cove, near everything Orleans has to offer!
Orleans House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $250 - $357 /nt
    $1,600 - $2,500 /wk
 
 
 
 
 

3 reviews write a review

Cape Cod Family Reunion - 4 homes on 2 private waterfront acres!
Orleans Estate Rental Picture
  • bedrooms 11
  • rental type Estate
  • owner badgeowner badge
  • sleeps 22
  • baths
  • rates (USD) $2,000 - $2,571 /nt
    $7,000 - $18,000 /wk
 
 
 
 
 

10 reviews write a review

Charming, comfortable home in Orleans near Rock Harbor --
Orleans House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $800 - $1,300 /wk
 
 
 
 
 

1 reviews write a review

House on Private Road, 2 min. to own secluded Bay Beach
Orleans House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,500 - $3,800 /wk
 
 
 
 
 

5 reviews write a review

Quiet & Convenient South Eastham Home Available
Orleans House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $1,995 /wk
 
 
 
 
 

1 reviews write a review