Orleans Vacation Rentals

Compare 2,360 available properties from 21 providers
Orleans
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Best Vacation Home Deals in Orleans

-64%
e.g. 5/4 - 5/11
Villa ∙ 16 guests ∙ 6 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $1,285 $3,570
Onefinestay
5.0
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-75%
e.g. 10/5 - 10/12
House ∙ 16 guests ∙ 6 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $999 $3,999
Onefinestay
5.0
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-52%
e.g. 1/5 - 1/12
House ∙ 6 guests ∙ 3 bedrooms
South Chatham, Chatham, Massachusetts, United States
from $295 $611
RedAwning
5.0
View deal

Compare and find a vacation rental that matches your needs among the 2,360 welcoming accommodations from 21 partner websites in Orleans. HomeToGo instantaneously shows the best offers by comparing all of the available vacation homes in Orleans from 21 different providers.

Recommended Vacation Rentals in Orleans

Rent a vacation accommodation in Orleans: from $80 per night

House ∙ 8 guests ∙ 4 bedrooms
Eastham, Orleans Town, Massachusetts, United States
from $81
VRBO
4.8
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House ∙ 4 guests ∙ 1 bedroom
Orleans, Orleans Town, Massachusetts, United States
from $159
VRBO
5.0
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Apartment ∙ 2 guests ∙ 1 bedroom
Orleans, Orleans Town, Massachusetts, United States
from $140
VRBO
4.8
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Apartment ∙ 2 guests ∙ 1 bedroom
Orleans, Orleans Town, Massachusetts, United States
from $100
VRBO
4.8
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House ∙ 5 guests ∙ 2 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $172
VRBO
4.4
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House ∙ 4 guests ∙ 2 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $214
VRBO
4.9
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House ∙ 4 guests ∙ 2 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $193
VRBO
4.8
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House ∙ 5 guests ∙ 3 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $100
VRBO
5.0
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House ∙ 6 guests ∙ 3 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $267
VRBO
4.7
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 4 guests ∙ 2 bedrooms
Eastham, Orleans Town, Massachusetts, United States
from $84
VRBO
4.6
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Fishing
Apartment ∙ 5 guests ∙ 2 bedrooms
Eastham, Orleans Town, Massachusetts, United States
from $96
VRBO
4.0
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Fishing
House ∙ 5 guests ∙ 2 bedrooms
Eastham, Orleans Town, Massachusetts, United States
from $90
VRBO
4.6
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 2 guests ∙ 1 bedroom
Orleans, Orleans Town, Massachusetts, United States
from $225
VRBO
4.9
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Fireplace
House ∙ 4 guests ∙ 2 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $78
VRBO
4.9
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Fireplace
House ∙ 6 guests ∙ 2 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $225
VRBO
4.8
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Apartments With Balconies or Patios

Balcony/Patio
House ∙ 4 guests ∙ 2 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $300
VRBO
5.0
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Balcony/Patio
House ∙ 6 guests ∙ 3 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $253
VRBO
4.9
View deal
Balcony/Patio
House ∙ 6 guests ∙ 3 bedrooms
Orleans, Orleans Town, Massachusetts, United States
from $116
VRBO
4.6
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Popular Rental Amenities in Orleans

  • Kitchen (2,282)
  • No smoking (2,275)
  • TV (2,096)
  • Grill (2,055)
  • Internet (2,040)
  • Microwave (1,992)
  • No pets (1,786)
  • AC (1,777)
  • Dishwasher (1,768)
  • Washer (1,727)
  • Parking (1,621)
  • Fireplace (842)
Use filters to look for an accommodation matching your requirements among all of the properties in Orleans. Most of the accommodations in Orleans provide "TVs" or "internet," which makes it a fantastic vacation spot if you want to tune out with some TV time or you can't imagine a vacation without internet. It is also possible to find a vacation rental in Orleans if you want a rental with a pool as 390 of the rentals there provide "pools."

Price and Availability Index in Orleans

Vacation Rental Price Information in Orleans

This graph displays average prices of the vacation rentals and holiday apartments located in Orleans. $375 is the highest price average in the next twelve months. On the other hand, in March you will find the cheapest prices (3/30 - 4/6). Prices this week are on average $310 a night.

Rental Availability Information in Orleans

Our availability graph helps you identify the busiest months in Orleans. The busiest time to book a rental in Orleans so far is in December (12/22 - 12/29), where only 58% rentals are available. It is easier to find a rental in a week of September (9/21 - 9/28), as only 18% of the accommodations are booked.

The Weather in Orleans

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27°
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27°
43°
30°
54°
41°
63°
50°
72°
57°
79°
66°
79°
64°
72°
59°
63°
50°
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39°
46°
34°
Jan.
Feb.
Mar.
Apr.
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June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

You can see our climate diagram above. During July, maximum temperatures go up to more than 78° On the contrary, the coolest month is January. The rainiest month is July while the driest month is August.

Accommodations in Orleans

In Orleans, house rentals are the most prevalent accommodation option. In addition, the median size of house rentals in Orleans is 1,910 ft² and they cost, on average, $449 per night. Furthermore, the majority of house rentals in Orleans can host groups of 8, which makes it a great vacation spot for large groups. You can also consider other types of accommodation in Orleans. Apartment rentals are, for example, another popular type of accommodation there with 130 offers to compare. Our data reveals that the average price of apartment rentals is $287 per night for an area of 1,300 ft².

Seaside delights galore with a vacation home in Orleans

The atmospheric seaside town of Orleans boasts a history steeped in whaling, fishing, and salt. Today, it attracts vacationers who come to explore the bounteous Cape Cod region. Waterfront vacation homes and villas serve as the perfect base while you discover Orleans.

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Food & Drinks

Orleans cooking

When it comes to dining, Orleans pulls out all the stops with its waterfront cafés, local pubs, and bright delis. For a romantic fine dining experience, Captain Linnell House impresses with its gourmet menu, classy cocktails, and wine. Chinese and Polynesian dishes, along with breezy waterfront vistas, await at the Double Dragon Inn.

Orleans's ubiquitous lobster rolls and fresh fried seafood are a must, as is the homemade ice cream sold at local parlors.

Nightlife

The nights are young

The Lost Dog Pub hosts weekend live music sessions and serves typical tavern specials such as wings and Philly cheese steaks. Stop by Orleans Bowling Center for its choice beers on tap, high-definition TVs, and arcade games. For "chowdah" with locals, the homey Yardarm Restaurant is the go-to place.

Night time theater is a favorite Orleans pastime, so make sure to catch a local production at the Academy of Performing Arts Playhouse or the Chatham Orpheum Theater, which has an on-site bistro that serves terrific appetizers and soups.

Local Attractions

Outdoor fun

One of the town's top-rated attractions is Nauset Beach, acclaimed for its golden dunes, bass fishing, and seals. Skaket Beach is perfect for families thanks to its low tidal pools and fine sand. Orleans's many freshwater lakes and ponds let you cool off, canoe, sunbathe, or angle away – Crystal Lake and Bakers Pond are recommended.

Biker-friendly Cape Cod Rail Trail traverses several towns, glacial ponds, dunes, and forests. Birdwatchers should make a stop at Nauset Marsh and Beach, Pochet Island, and Skaket Beach. Meanwhile, Wellfleet Bay Wildlife Sanctuary is home to beautiful salt marshes, sandy barrier beaches, and raptors.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Orleans VRBO Vacation Rentals in Orleans HomeAway Vacation Rentals in Orleans TripAdvisor Vacation Rentals in Orleans VacationRentals.com Vacation Rentals in Orleans HouseTrip Vacation Rentals in Orleans FlipKey Vacation Rentals in Orleans 9flats.com Vacation Rentals in Orleans VaycayHero Vacation Rentals in Orleans PerfectPlaces.com Vacation Rentals in Orleans Homestay.com Vacation Rentals in Orleans Only-apartments Vacation Rentals in Orleans Interhome Vacation Rentals in Orleans Bedycasa Vacation Rentals in Orleans Novasol Vacation Rentals in Orleans HomeEscape Vacation Rentals in Orleans

Vacation Destinations Near Orleans