Orleans holiday rentals

We found 3,178 holiday rentals — enter your dates for availability
Select from 286 homes, 19 cottages and other holiday rentals in Orleans to find one that's perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll have the amenities that you expect and more, which might include Wi-Fi and a fireplace. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Orleans

Showing deals for:27 Nov - 4 Dec

Living area
Exterior
Outdoor dining
Private kitchen
Wonderful
(19 reviews)

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
AU$1,094
for 7 nights, 1 cottage
AU$156 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Full view of backyard with in ground pool
Backyard view of house
Large family room with lots of seating; perfect for family game night
Pool house: a quiet hideaway or remote office
Exceptional
(29 reviews)

Immaculately maintained, large beach home with heated swimming pool

Eastham

8% off
AU$7,846
for 7 nights, 1 home
AU$1,121 per night
includes taxes & fees
Immaculately maintained, large beach home with heated swimming pool
Refreshing outdoor shower
Wet bar in the pool room
two-story entrance Foyer
Game room with beautiful pool table and wet bar.
Exceptional
(24 reviews)

Spacious home - Sleeps 15 -Steps to a Private Beach

Dennis

8% off
AU$11,817
for 7 nights, 1 home
AU$1,688 per night
includes taxes & fees
Spacious home - Sleeps 15 -Steps to a Private Beach
Downstairs bedroom
Private beach/dock area
Living room
View of property
Exceptional
(18 reviews)

Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View

South Chatham

8% off
AU$9,693
for 7 nights, 1 home
AU$1,385 per night
includes taxes & fees
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Interior
Deck with teak table and chairs
Living room with cathedral ceiling - open floor plan
Flowering plantings including blue hydrangea, lilac and magnolia
Exceptional
(91 reviews)

Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Chatham

8% off
AU$5,074
for 7 nights, 1 home
AU$725 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Light & bright second floor great room
Deeded access to nearby Mill Pond to launch your Kayak
Fabulous family room, a magnet for family gatherings
Well equipped chef's kitchen w. stainless steel appliances
Exceptional
(119 reviews)

Water View-Walk town/beach, pets considered, Linen Option

Chatham

19% off
AU$9,302
for 7 nights, 1 home
AU$1,329 per night
includes taxes & fees
Water View-Walk town/beach, pets considered, Linen Option
Breakfast Nook With Pool and Tranquil Forest View
Breakfast Nook with Pool View
Second Deck Bar Sitting/Dining Area
New Chefs Kitchen
Exceptional
(36 reviews)

Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf/Lakes

Brewster

7% off
AU$6,824
for 7 nights, 1 home
AU$975 per night
includes taxes & fees
Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf/Lakes
entrance to mallardview
Exterior
Private kitchen
Interior
Exceptional
(61 reviews)

5 bedrooms ocean view estate overlooking cape cod bay

Orleans

8% off
AU$11,031
for 7 nights, 1 home
AU$1,576 per night
includes taxes & fees
5 bedrooms ocean view estate overlooking cape cod bay
Hallway
Backyard
Downstairs game and movie room
Back of house
Exceptional
(21 reviews)

Peaceful Cape Cod retreat, 1.5mi to National Seashore

Orleans

8% off
AU$7,033
for 7 nights, 1 home
AU$1,005 per night
includes taxes & fees
Peaceful Cape Cod retreat, 1.5mi to National Seashore
Pool house
Center island with seating for 4
2000+ SF multi level patio, pool, pool house, outdoor kitchen, fire pit & more!
Fire pit & couch
Exceptional
(43 reviews)

Chatham Loop/Stage Neck/5 Bed/6 Bath

Chatham

8% off
AU$13,050
for 7 nights, 1 home
AU$1,864 per night
includes taxes & fees
Chatham Loop/Stage Neck/5 Bed/6 Bath
Master Bedroom - King Bed, TV, Bureau and ensuite bath
Shuffle Board
Living Room
Kitchen, Dining area: Fridge, Stove, Dishwasher
Exceptional
(137 reviews)

#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat

Harwich

7% off
AU$3,373
for 7 nights, 1 home
AU$482 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Family room with TV enclosed in built-in millwork
Eat-in kitchen with oversized island is great for entertaining
Mudroom and laundry
Primary bedroom (king bed)
Exceptional
(28 reviews)

Family friendly luxury home with heated pool and spa

Chatham

8% off
AU$10,088
for 7 nights, 1 home
AU$1,441 per night
includes taxes & fees
Family friendly luxury home with heated pool and spa
Living Room Features Ocean View, TV streaming with Netflix, Hulu, YouTube TV
Relax and Entertain Friends and Family on the Large Stone Patio
Escape to your private oceanfront property!
Dining
Exceptional
(140 reviews)

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Chatham

7% off
AU$8,465
for 7 nights, 1 home
AU$1,209 per night
includes taxes & fees
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Dining
Living area
Room
Private kitchen
Exceptional
(15 reviews)

Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball

Chatham

11% off
AU$4,214
for 7 nights, 1 home
AU$602 per night
includes taxes & fees
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
Pine Room/Family room with queen pull out couch
Marina
Exterior
Interior
Exceptional
(43 reviews)

Rates just lowered for last week of July and Aug with 5 night min accepted.

South Dennis

7% off
AU$1,997
for 7 nights, 1 home
AU$285 per night
includes taxes & fees
Rates just lowered for last week of July and Aug with 5 night min accepted.
Living room looking toward front
Living room looking toward front / first floor front bedroom door
Kitchen
Second floor front bedroom with view of Cape Cod Bay
Exceptional
(28 reviews)

Waterview, 4 BR, 100 Feet from Private Eastham Bayside Beach!

Eastham

6% off
AU$4,811
for 7 nights, 1 home
AU$687 per night
includes taxes & fees
Waterview, 4 BR, 100 Feet from Private Eastham Bayside Beach!
The Woolrych House sits above a private Brewster beach.
Outdoor dining
View from second floor.
Dinner with a view.
Exceptional
(50 reviews)

Picturesque Private Beachfront House on Cape Cod Bay

Brewster

8% off
AU$4,997
for 7 nights, 1 home
AU$714 per night
includes taxes & fees
Picturesque Private Beachfront House on Cape Cod Bay
Exterior
Private kitchen
Outdoor dining
Living area
Exceptional
(11 reviews)

3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.

Dennis

7% off
AU$3,944
for 7 nights, 1 home
AU$563 per night
includes taxes & fees
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Large LR w/ wood burning fireplace, Samsung Frame TV &expansive picture window.
Propane fire-pit for cool nights. Evening view.
Marble counters, KitchenAid appliances & gas stove. All overlooking the water.
Charming & cozy.
Exceptional
(28 reviews)

★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets

Brewster

8% off
AU$6,986
for 7 nights, 1 home
AU$998 per night
includes taxes & fees
★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets
Room
Outdoor dining
Exterior
Dining
Exceptional
(31 reviews)

Sun-filled, renovated house within minutes walk to private bay sides beach.

Eastham

7% off
AU$4,560
for 7 nights, 1 home
AU$651 per night
includes taxes & fees
Sun-filled, renovated house within minutes walk to private bay sides beach.
Dining
The Chatham downtown is filled with cute shops and restaurants.
Living area
Private kitchen
Exceptional
(7 reviews)

Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham

North Chatham

8% off
AU$5,157
for 7 nights, 1 home
AU$737 per night
includes taxes & fees
Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham
Property grounds
Private kitchen
Living area
Living area
Exceptional
(5 reviews)

Adorable updated Cape in East Orleans!

Orleans

8% off
AU$6,755
for 7 nights, 1 home
AU$965 per night
includes taxes & fees
Adorable updated Cape in East Orleans!
Living area
Dining room with water views
Study/Lounge are with water views
Terrace/patio
Exceptional
(35 reviews)

Steps to Paine's Creek-The Perfect Vacation Home

Brewster

7% off
AU$5,496
for 7 nights, 1 home
AU$785 per night
includes taxes & fees
Steps to Paine's Creek-The Perfect Vacation Home
Eat in kitchen. Enjoy the lobsters!
Welcome to the porch where you can relax after a day at the beach or golfing!
A place to rest your head after all the fun you will have here!
Exterior
Wonderful
(65 reviews)

Delightful Cottage for Two

Chatham

8% off
AU$2,333
for 7 nights, 1 cottage
AU$333 per night
includes taxes & fees
Delightful Cottage for Two

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Take in the beachside beauty of Orleans

The beaches and other outdoor surroundings create an inviting atmosphere in Orleans. Renowned for its seafood restaurants, baseball games and university setting, this city welcomes all visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Orleans

Are you searching for things to do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Orleans a one-of-a-kind holiday spot. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Ocean Edge Golf Club (3.8 mi / 6.2 km)
  • Cape Cod Lavender Farm (8.2 mi / 13.3 km)
  • Cape Cod Baseball & Bumper Boats (9.8 mi / 15.7 km)
  • Cape Cod Inflatable Park (15.9 mi / 25.5 km)
  • Rail Trail Bike Shop (4.6 mi / 7.3 km)
  • Adventure Chatham (6.5 mi / 10.5 km)

Exploring the natural landscape of Orleans

Whether you're an active traveller or just want to appreciate the scenery, Orleans is a great place to get out in nature. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Cape Cod Beaches (10.5 mi / 16.9 km)
  • Skaket Beach (1.4 mi / 2.3 km)
  • Nauset Beach (3.5 mi / 5.7 km)
  • Nauset Light Beach (3.7 mi / 6 km)
  • Breakwater Beach (5.1 mi / 8.2 km)
  • Marconi Beach (7.1 mi / 11.4 km)

Seasonal weather in Orleans

If you're planning a holiday around the weather, August, July, September and June are the hottest months to visit, when temperatures average 19°C.

Travelling to and around Orleans

Fly into Hyannis, MA (HYA-Barnstable Municipal), the closest airport, located 17.5 mi (28.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Provincetown, MA (PVC-Provincetown Municipal), which is 23 mi (37 km) away.

Frequently asked questions

What is the best area to stay in Orleans when booking a holiday rental?
When considering a holiday rental in Orleans, Massachusetts, the best area to stay would be around the charming village centre. This area offers a delightful blend of local character and convenience, with easy access to various attractions. Not far from the village, you can explore the stunning Cape Cod National Seashore, which boasts breathtaking coastal scenery and lovely walking trails.Additionally, the nearby Nauset Beach is a fantastic spot for sunbathing, swimming, and enjoying the picturesque views of the Atlantic Ocean. The village centre itself features a selection of unique shops and local eateries, providing a taste of the local culture. There are a number of properties available in this area, suiting a range of preferences and budgets, making it an appealing choice for visitors looking to experience the best of Orleans.
Where are the best areas for renting a beach house in Orleans?
For renting a beach house in Orleans, Massachusetts, the area surrounding Nauset Beach is an excellent choice. This picturesque stretch of coastline offers holiday rentals that provide easy access to the sandy shores and stunning views of the Atlantic Ocean. Many properties in this vicinity come equipped with amenities such as outdoor decks, private patios, and well-appointed kitchens, which are superb for families or groups looking to enjoy a relaxing beach getaway.Additionally, the nearby Skaket Beach area is known for its shallow waters, making it ideal for families with young children. Here, you'll find charming cottages and larger homes that often feature outdoor showers, barbecues, and spacious backyards, enabling guests to fully embrace the coastal lifestyle. The proximity to local shops and restaurants in Orleans enhances the convenience for travellers looking to explore the local culinary scene.For those interested in outdoor activities, the surrounding Cape Cod National Seashore provides numerous opportunities for hiking, biking, and birdwatching, adding an adventurous element to the beach experience. Rentals in this area often reflect a coastal aesthetic, with amenities like air conditioning, Wi-Fi, and easy access to scenic paths leading directly to the beach.
What is the most popular type of holiday rental accomodation in Orleans?
In Orleans, holiday houses are the most popular type of holiday rental, with about 1,028 available in the area. These properties are often situated near serene beaches and picturesque landscapes, providing a superb base for exploring the natural beauty of Cape Cod. Most holiday houses come equipped with fully stocked kitchens, spacious living areas, and outdoor patios or decks ideal for barbecues and relaxation after a day of beach activities.Additionally, there are around 64 cottages available, which offer a charming, cosy atmosphere, often featuring rustic decor and easy access to local attractions such as the Cape Cod National Seashore. For those seeking smaller accommodations, there are 24 apartments and 16 condos, typically located close to shops and restaurants, providing convenience for travellers.
Are there any family house rentals in Orleans?
In Orleans, Massachusetts, families will find a wealth of rental options—there are 219 properties available specifically suited for family stays. The town is located on Cape Cod, offering beautiful beaches and charming local attractions. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for children to play. Guests can expect amenities such as Wi-Fi, air conditioning, and sometimes even private patios or gardens for relaxation after a day of exploring.The neighbourhoods around Orleans, including East Orleans and South Orleans, provide easy access to scenic spots like Nauset Beach, known for its gentle waves and family-friendly atmosphere. Additionally, visitors can enjoy local shops, restaurants, and the nearby Cape Cod Rail Trail for cycling and walking adventures.
Can I rent a holiday home with a pool or hot tub in Orleans?
In Orleans, Massachusetts, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 34 options to choose from. This charming coastal town, located on Cape Cod, is known for its beautiful beaches and picturesque landscapes. Many of these properties are situated near popular spots like Skaket Beach and Nauset Beach, providing easy access to sandy shores and stunning sunsets.Travellers can expect a variety of amenities in these rentals, including private swimming pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a seaside getaway. Some homes may also feature additional comforts such as outdoor grills, fire pits, and comfortable lounge areas, great for entertaining or unwinding after a day of beach activities.
Are there pet-friendly house rentals in Orleans?
In Orleans, Massachusetts, there are numerous pet-friendly house rentals available, offering a great variety of options for travellers with furry companions. The town features charming properties that typically come equipped with amenities such as fully stocked kitchens, outdoor spaces, and comfortable living areas, making them ideal for family stays or group getaways. Many of these rentals also provide access to essential conveniences like Wi-Fi and laundry facilities.Orleans is located near beautiful beaches, including Nauset Beach and Skaket Beach, where you and your pet can enjoy long walks along the shore. Additionally, the nearby Cape Cod Rail Trail offers ample opportunities for biking and walking, allowing for a great day out with your pet amidst the scenic surroundings. The area is also home to several pet-friendly parks and local eateries that welcome dogs, creating an inviting space for pet owners.
Are there any remote work holiday rentals in Orleans?
In Orleans, Massachusetts, there are numerous remote work holiday rentals available, with around 1,076 options to choose from. This charming town on Cape Cod is an excellent choice for those looking to blend work and leisure. Many properties come equipped with high-speed Wi-Fi and dedicated office spaces, making it easy to stay productive while enjoying the picturesque surroundings.Travellers can expect a variety of accommodations, from cosy cottages to spacious family homes, often featuring amenities such as fully equipped kitchens, outdoor patios, and comfortable living areas. The town is also close to beautiful beaches and scenic walking trails, offering a great balance between work and relaxation. Local attractions, including shops and dining options, add to the convenience for those staying in the area. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Orleans?
In Orleans, popular holiday rental amenities typically include kitchens, allowing guests to prepare their own meals, and decks or patios, which provide lovely outdoor spaces for relaxation and dining. Additionally, many properties feature coffee and tea makers, ensuring that guests can enjoy their morning beverages at leisure. Onsite parking is also commonly available, making it convenient for those travelling by car.
When is the best time to visit Orleans for a holiday rental?
The peak season for visiting Orleans is during the summer months of June to August, with July being the most popular time. This vibrant period attracts families and beach lovers, eager to soak up the sun on Cape Cod's beautiful shores and engage in numerous outdoor activities like boating, fishing, and exploring the picturesque coastal scenery.During these months, visitors can expect warm temperatures, typically ranging from 20 to 30 degrees Celsius, creating an inclusive setting for beach days and seaside adventures. The bustling summer vibe includes local festivals, farmers' markets, and plenty of opportunities to enjoy fresh seafood at charming eateries.For those seeking a quieter experience with still pleasant weather, consider visiting in November. This month offers a fantastic opportunity to enjoy the stunning autumn colours along the coast, with fewer crowds and a more relaxed pace. You can take tranquil walks along the beach or explore the scenic trails without the hustle and bustle of peak season.
What are the top attractions in Orleans?
In Orleans, Massachusetts, visitors can enjoy a range of attractions that showcase the charm of Cape Cod. The town is known for its beautiful beaches, with Nauset Beach being a popular choice for sunbathing, swimming, and surfing, offering stunning views of the Atlantic Ocean. Nearby, Skaket Beach is great for families, featuring calm waters ideal for children and picturesque sunsets.The quaint Main Street is home to a variety of local shops, galleries, and eateries, giving visitors a taste of the local culture and cuisine. For nature enthusiasts, the Cape Cod National Seashore is easily accessible and provides opportunities for hiking, birdwatching, and exploring scenic coastal landscapes.Additionally, the Orleans Historical Society offers insights into the town's rich history, making it a worthwhile stop for those interested in learning more about the area.
Are all fees included in the Orleans holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Orleans holiday homes with parking?
Stayz offers a wide selection of holiday homes in Orleans with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Orleans holiday homes?
You can find great discounts on holiday homes in Orleans on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Orleans holiday home booking on Stayz?
To find Orleans holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Orleans?
A long-stay holiday home in Orleans is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Orleans holiday home?
Book your Orleans holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Orleans?
Prices for holiday homes in Orleans vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Orleans to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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