Holiday rentals in Orleans

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Orleans

  • Total holiday rentals

    Explore 380 holiday rentals in Orleans

  • Nightly prices starting at

    Orleans holiday rentals start at $91 SGD per night before taxes and fees

  • Verified guest reviews

    Over 10,970 verified reviews to help you choose

  • Family-friendly holiday rentals

    310 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 130 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wifi availability

    380 of Orleans holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Beachfront, Self check-in and Gym across Orleans rentals

  • 4.8 Average rating

    Orleans stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Orleans

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Guest suite in Orleans
4.9 out of 5 average rating, 224 reviews

Charming Old Cape Cod

Indulge in relaxation and leisure at Snowtop on the Town Cove. The charming retreat features a private entrance, a spacious bedroom with a king size bed, a full bath, and a sunlit living room with a dining table overlooking picturesque Town Cove. The view in the photo is your front yard. Guests often enjoy sitting outside to watch boats drift by and the sky change color to a sunset. Nestled on a quiet road, Snowtop is 3 miles from beautiful Nauset Beach and 2 miles from the center of Orleans.

Top guest favourite
Home in Orleans
5 out of 5 average rating, 40 reviews

Steps to Rock Harbor | AC, Deck, Outdoor Shower

Welcome to Rock Harbor! Just steps from one of Orleans’ most loved harbor areas, this newly renovated Cape Cod cottage blends classic coastal charm with modern comfort. Whether you're heading to the beach, catching a sunset at Rock Harbor, exploring the National Seashore, or day-trip to Provincetown, Chatham, or Hyannis, this is an easy & relaxing place to come home to. Perfect for families, couples, or friends, the cottage sleeps up to 6 & has been thoughtfully designed for a comfortable stay.

Top guest favourite
The private yard features a fire pit surrounded by blue chairs, with a small patio table and umbrella nearby. Lush greenery and flowering plants line the path, leading to the entrance of the cottage, while a wooden fence provides a sense of seclusion.
Home in Orleans
4.96 out of 5 average rating, 27 reviews

Antique Cottage with Path to Arey’s Pond

Relax at this unique and tranquil escape. Our small but charming one bedroom cottage offers a compact kitchen and a small full bath. A true antique from 1850, the unit is updated but remains quintessential Old Cape Cod. Private yard, outdoor shower, fire pit, laundry, and access to Arey’s Pond 350 yds down private path. A pet friendly getaway for a couple looking to relax in an ideal Orleans location. Close to Nauset Beach, Orleans, Chatham, shops & great dining. A super place to vacation.

Top guest favourite
An aerial view captures a cottage nestled among vibrant green trees, showcasing the surrounding natural landscape. A glimpse of the ocean is visible in the distance. The cottage features a deck facing the woods, providing a serene and secluded ambiance.
Home in Orleans
5 out of 5 average rating, 31 reviews

Peaceful Nauset Beach Sanctuary

Imagine driving down a quiet private dirt road behind one of the nicest beaches on Cape Cod. Enter the property through a gate and walkway and you’re in your own private sanctuary. The cottage feels like a treehouse looking onto the tidal marsh behind Nauset Beach. Inside you will feel the vibes of a nostalgic cape cod cottage with modern amenities and style. Chill out on the deck. Take a 10 minute walk to a private section of Nauset Beach or drive to our free association Nauset parking lot.

Top guest favourite
Home in Eastham
5 out of 5 average rating, 8 reviews

10 min walk to Beach - Amazing View & Huge Deck

Enjoy an incredible view of Duck Meadow Tidal Marsh from this cozy cottage. Only a 10 minute walk to Boat Meadow Landing, a great bayside beach. Sip your morning coffee on our huge deck while enjoying the view. The deck includes a retractable roof if you would prefer to sit in the shade. Only minutes from incredible restaurants & shops in Orleans. This home includes AC, office space w/ monitors & a natural gas fireplace. Near the Cape Cod Rail Trail, hiking trails and numerous beach options!

Top guest favourite
The exterior of the modern home is visible, featuring a spacious deck with a dining table and teal chairs. Lush greenery and colorful flowers surround the area, while a light blue umbrella adds shade. A grill is positioned nearby, creating an inviting outdoor dining space.
Home in Orleans
5 out of 5 average rating, 24 reviews

Quiet, Sleeps 6, 2 Full Ba, 5 min Drive to Beach

This unique mid century modern home is located near the river leading to pleasant bay. Just 5 minutes to Orleans center and all the beaches in town. After a day at the beach you can enjoy an afternoon swim at Crystal Lake or Pilgrim Lake just a 10 minute walk away followed by a serene evening in one of our outdoor seating spaces. .6 miles to Crystal Lake 2.2 miles to the Cape Cod Rail Trail 2.9 miles to Nauset Beach 3 miles to Skatet Beach 3.4 miles to Nickerson State Park

Top guest favourite
A charming cottage is set amidst well-maintained landscaping, featuring shingle siding and a welcoming front porch. Natural light is evident in the multiple windows, and the property is enclosed by neatly trimmed hedges, offering privacy and a cozy atmosphere.
Home in Orleans
5 out of 5 average rating, 79 reviews

4 Season Cottage, Nauset Beach, tennis court

A four-season, luxurious, cottage-style retreat near the glorious beaches on the North spit of Nauset Beach, off Nauset Heights. Tennis court, ample grounds, walking neighborhood, and easy beach access. This Property is shared with two seasonal cottages. Perfect for getaways, the cottage is designed for a couple or individual. While there are two twins downstairs, these are appropriate for children, a friend, or a relative who will not be jealous of the king room upstairs.

Superhost
Home in Orleans
4.78 out of 5 average rating, 60 reviews

Wequasset House - Quiet, spacious beach base

No cleaning fees! Keep it simple at this peaceful and centrally-located furnished home base for your Cape Cod adventures! Cozy 3-bed, 2-bath ranch house with deck. 3pm check in & 10am check out All rooms have end tables with built in charging. Bedrooms have window AC units & mini split in living room. Coffee station in kitchen with KCups refreshed in May New for 2026: 1. New larger living room couch 2. Couch in bunk bedroom 3. TV with Roku added to master bedroom

Guest favourite
A spacious backyard is surrounded by trees and features a well-maintained lawn. The house is visible in the background, with a light-colored exterior and multiple windows. A hammock is suspended between two trees, creating a relaxed outdoor space.
Home in Orleans
4.93 out of 5 average rating, 28 reviews

Orleans, MA Luxury Getaway

Enjoy the best the Cape has to offer! Stay at this hidden gem in Orleans, MA. Easy access to Nauset Beach and Little Pleasant Bay. Large, luxurious, and family friendly with a big yard in a quiet neighborhood. Enjoy our gazebo, firepit, outdoor grill, outdoor patio dining, and outdoor shower. Inside, luxuriate in this 4 bed 4 bathroom with a modern kitchen, breakfast nook, dining room, and living room. Washer and dryer included in basement.

Top guest favourite
A large arched window frames a serene water view, with trees and nearby buildings visible outside. A decorative swan ornament rests on the window sill, adding a charming touch to the scenic backdrop of the cove and sky.
Cottage in Orleans
4.97 out of 5 average rating, 96 reviews

Cozy Condo/Cottage on Cove, Walk to Town

Welcome! Enjoy a Fabulous 180 degree water view out our master bedroom and living room. Walk to Orleans village, art galleries, restaurants & shopping. Bike to Beaches and baseball all within a mile. One floor condo is good for couples, solo adventurers, small families. One full bath with shower and one half bath, plus a new outdoor shower. Master BR has Queen bed. Second BR has a queen bed with a twin trundle pull out.

Top guest favourite
An outdoor gathering area is arranged around a circular fire pit, with several comfortable chairs and accent tables. The surrounding garden is filled with lush greenery and vibrant blue hydrangeas. Soft lighting enhances the cozy ambiance as twilight descends.
Home in Orleans
4.99 out of 5 average rating, 104 reviews

Walk to Lake + Fire Pit | Near Nauset + Sleeps 10

Let the Cape Cod breeze clear your thoughts and the sound of birdsong reset your pace. This beautifully renovated Orleans retreat sits on a quiet wooded lot — walk 5 minutes to Pilgrim Lake, stroll through the woods to Arey's Pond, or drive 7 minutes to Nauset Beach. Three bedrooms sleep up to 10, with a designer coffee bar, firepit, grill station, and game room waiting for you. There is a lot to donor nothing at all.

Top guest favourite
A sandy path meanders through tall grass, leading toward a tranquil sunset in the background. The sun casts a warm glow over the horizon, suggesting the evening calm of the beach area. Soft greens and earthy tones create a peaceful natural setting.
Flat in East Orleans
4.95 out of 5 average rating, 325 reviews

Cozy Waterfront Apartment, Private Beach Access

Charming living space with nautical decor invites you to unwind off the grid for a few days. There is a window seat for reading, small high top for morning coffee, and all the accessories for a relaxing day at the beach. A five minute drive into town for local shopping and dining. Many scenic trails for walking and biking. Make us your base as you explore Cape Cod’s beautiful shores!

Popular amenities for Orleans holiday rentals

When is the best time to visit Orleans?

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Avg. price$421 SGD$415 SGD$405 SGD$430 SGD$408 SGD$494 SGD$595 SGD$599 SGD$415 SGD$413 SGD$421 SGD$448 SGD
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Frequently Asked Questions

  • What types of vacation rentals are available in Orleans?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Orleans. From over 270 house rentals to over 30 cottage rentals, we've got you covered.

  • Are there vacation rentals with a dedicated workspace in Orleans?

    Yes! Work meets play with ease at over 210 vacation rentals in Orleans featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Orleans?

    Four-legged friends are welcome in Orleans. Choose from more than 130 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in cottage rentals in Orleans?

    Experience the best of Orleans with our cottage rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do cottage rentals in Orleans have self check-in?

    Absolutely! We offer over 10 cottage rentals with self check-in in Orleans. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Orleans have a bbq area?

    Absolutely! We offer over 30 cottage rentals with a bbq area in Orleans. Enjoy a tailored experience with all the comforts you desire.

  • Are there Orleans house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 house rentals with pools in Orleans, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Orleans have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Orleans. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cottage rentals in Orleans?

    Orleans has more than 20 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Cottage Rentals in Orleans?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 30 homes with a bbq area, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.