Orleans Holiday Rentals

Compare Villas, Resorts, & Rentals in Orleans, Massachusetts, USA

Private Lake Access Great for Families
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10.0 (2 Reviews)
3 Bedrooms 7 Guests
The Parsonage Inn
FromR4,028 per night
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9.8 (35 Reviews)
1 Bedroom 2 Guests
Nauset Heights Carriage House
New
1 Bedroom 2 Guests
Gorgeous Renovation Walk to Water
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10.0 (2 Reviews)
3 Bedrooms 6 Guests
Ship's Knees Inn
FromR6,302 per night
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9.6 (26 Reviews)
1 Bedroom 2 Guests
Walk to Water, Cozy, Dog Friendly!
New
3 Bedrooms 8 Guests
4-5 Min to Mill Pond or Nauset Beach
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10.0 (2 Reviews)
4 Bedrooms 9 Guests
Olde Tavern Motel And Inn
9.4 (237 Reviews)
1 Bedroom 2 Guests
Waterfront Fun at this Huge Family Estate
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10.0 (1 Review)
11 Bedrooms 23 Guests
1 min drive to Rock Harbor, 2 min to Town!
10.0 (39 Reviews)
2 Bedrooms 5 Guests
Ocean Views New A C Dog Welcome
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10.0 (1 Review)
5 Bedrooms 11 Guests
Cape Cod Sunscape. Orleans
10.0 (17 Reviews)
2 Bedrooms 6 Guests
Spacious Game Room Close to Nauset Beach
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10.0 (1 Review)
4 Bedrooms 12 Guests
Stunning Home with In-Ground Pool
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10.0 (1 Review)
4 Bedrooms 8 Guests
Beach Getaway with Private Backyard
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10.0 (1 Review)
4 Bedrooms 10 Guests
Pondfront 1 Mile to Nauset Beach
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10.0 (1 Review)
3 Bedrooms 8 Guests
Steps to Rock Harbor, Fully Renovated Cape Cod Cottage
10.0 (9 Reviews)
2 Bedrooms 6 Guests
Association Beach less than a Mile away
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10.0 (1 Review)
3 Bedrooms 6 Guests
Quiet Neighborhood .2 miles to Skaket Beach (1193)
10.0 (6 Reviews)
2 Bedrooms 6 Guests
10 ft from Crystal Lake New renovation
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10.0 (1 Review)
3 Bedrooms 6 Guests
Bed, Splash & Beyond – Coastal Comfort Awaits
10.0 (6 Reviews)
1 Bedroom 4 Guests
15 min Walk to Nauset Beach
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10.0 (1 Review)
3 Bedrooms 6 Guests
Refurbished Cottage with Views of Town Cove (1038)
10.0 (3 Reviews)
2 Bedrooms 4 Guests
Newly updated spacious steps to water
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10.0 (1 Review)
2 Bedrooms 4 Guests
Perfectly private location w deeded beach access
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10.0 (1 Review)
3 Bedrooms 6 Guests
East Orleans Waterview Getaway
10.0 (2 Reviews)
2 Bedrooms 6 Guests
Beach & Golf Hub w/All-Season Sunroom in Cape Cod
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10.0 (1 Review)
5 Bedrooms 9 Guests
The Parsonage
FromR6,306 per night
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9.8 (9 Reviews)
10 Bedrooms 22 Guests
Orleans Beach Retreat
FromR6,750 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
Bike to Nauset Beach or Walk to Mill Pond
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9.5 (11 Reviews)
3 Bedrooms 6 Guests
Studio, Walk to Nauset Beach!
FromR3,181 per night
10.0 (1 Review)
1 Bedroom 3 Guests
East Orleans - walk to Nauset Beach
9.8 (83 Reviews)
2 Bedrooms 4 Guests
Romantic Orleans Waterfront Cottage!
9.8 (31 Reviews)
1 Bedroom 2 Guests
Adorable home in the heart of East Orleans!
9.8 (28 Reviews)
2 Bedrooms 5 Guests
Spacious Orleans Apartment With Private Beach Access
9.8 (26 Reviews)
1 Bedroom 4 Guests
Amazing location! Quiet, picturesque neighborhood!
10.0 (117 Reviews)
3 Bedrooms 6 Guests
Waterfront amazing views near beaches
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9.3 (3 Reviews)
3 Bedrooms 6 Guests
Nauset Beach Inn
FromR4,588 per night
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9.4 (176 Reviews)
1 Bedroom 2 Guests
Luxury 7 BR, 4 BA w/Unique 60 ft Pool, .4 Miles to Beach
10.0 (74 Reviews)
7 Bedrooms 21 Guests
Steps to Skaket Beach
FromR14,769 per night
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9.0 (3 Reviews)
4 Bedrooms 8 Guests
Skaket Beach Motel
FromR1,874 per night
9.2 (450 Reviews)
1 Bedroom 2 Guests
Gray Gables
FromR10,970 per night
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9.0 (2 Reviews)
1 Bedroom 6 Guests
Rodeway Inn Orleans - Cape Cod
8.2 (806 Reviews)
1 Bedroom 2 Guests
Close To World Class Beaches And Village
10.0 (67 Reviews)
5 Bedrooms 12 Guests
Amazing Outdoor Space Access to Town Cove
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9.0 (1 Review)
5 Bedrooms 12 Guests
Less than 5 Miles to Rock Harbor
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9.0 (1 Review)
4 Bedrooms 9 Guests
1 min drive to Rock Harbor 2 min to Town
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9.0 (1 Review)
2 Bedrooms 5 Guests
Quaint Cape Near Beaches And Centrally Located
10.0 (51 Reviews)
3 Bedrooms 6 Guests
Barley Breeze
FromR4,093 per night
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9.0 (1 Review)
1 Bedroom 8 Guests
5 Min Walk to Nauset Beach, Saltwater Heated Pool & Hot Tub
10.0 (50 Reviews)
5 Bedrooms 12 Guests
Cozy Cottage Walk to Nauset Beach
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9.0 (1 Review)
3 Bedrooms 6 Guests
Ship's Knees Inn
FromR4,862 per night
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8.7 (26 Reviews)
15 Bedrooms 37 Guests
Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket
10.0 (42 Reviews)
4 Bedrooms 10 Guests
2 mins from Nauset Beach
FromR6,075 per night
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8.5 (10 Reviews)
2 Bedrooms 4 Guests
Spinnaker Trail
FromR11,707 per night
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8.5 (4 Reviews)
8 Bedrooms 16 Guests
Waterfront. Private beach. Pool. Estate has it all!
10.0 (35 Reviews)
9 Bedrooms 19 Guests
The Perfect Beach Getaway
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8.5 (2 Reviews)
3 Bedrooms 6 Guests

About Casai's Private Villas and Holiday Rentals in Orleans

Discover more than 640 vacation rentals available in Orleans. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Orleans.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Orleans, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Orleans. On average, places to stay near Orleans offer 1393.43 ft², with nightly prices averaging R12,467.

With Casai, finding and comparing holiday rentals in Orleans is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.