Orleans holiday rentals

We found 3,179 holiday rentals — enter your dates for availability
Select from 287 homes, 20 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:13 Nov - 20 Nov

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

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
S$1,024
for 7 nights, 1 cottage
S$146 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Full view of backyard with in ground pool
Backyard view of house
Pool house: a quiet hideaway or remote office
Large family room with lots of seating; perfect for family game night
Exceptional
(29 reviews)

Immaculately maintained, large beach home with heated swimming pool

Eastham

8% off
S$7,517
for 7 nights, 1 home
S$1,074 per night
includes taxes & fees
Immaculately maintained, large beach home with heated swimming pool
New Chefs Kitchen
Breakfast Nook with Pool View
Breakfast Nook With Pool and Tranquil Forest View
Second Deck Bar Sitting/Dining Area
Exceptional
(35 reviews)

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

Brewster

7% off
S$6,539
for 7 nights, 1 home
S$934 per night
includes taxes & fees
Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf/Lakes
Exterior
Pool
Living area
Living area
Exceptional
(68 reviews)

Luxury 8 Bedroom Home with Heated Pool - 4 minutes to the beach! Pet Friendly!

Orleans

8% off
S$15,911
for 7 nights, 1 home
S$2,273 per night
includes taxes & fees
Luxury 8 Bedroom Home with Heated Pool - 4 minutes to the beach! Pet Friendly!
Living room
Private beach/dock area
Downstairs bedroom
View of property
Exceptional
(18 reviews)

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

South Chatham

8% off
S$9,257
for 7 nights, 1 home
S$1,322 per night
includes taxes & fees
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Mudroom and laundry
Eat-in kitchen with oversized island is great for entertaining
Primary bedroom (king bed)
Hot tub spa
Exceptional
(28 reviews)

Family friendly luxury home with heated pool and spa

Chatham

7% off
S$8,403
for 7 nights, 1 home
S$1,200 per night
includes taxes & fees
Family friendly luxury home with heated pool and spa
Large island, comfortable seating area
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

25% off
S$6,776
for 7 nights, 1 home
S$968 per night
includes taxes & fees
Water View-Walk town/beach, pets considered, Linen Option
two-story entrance Foyer
Wet bar in the pool room
Refreshing outdoor shower
Sun filled porch with dining for 10.
Exceptional
(24 reviews)

Spacious home - Sleeps 15 -Steps to a Private Beach

Dennis

7% off
S$11,102
for 7 nights, 1 home
S$1,586 per night
includes taxes & fees
Spacious home - Sleeps 15 -Steps to a Private Beach
Downstairs game and movie room
Backyard
Back of house
Hallway
Exceptional
(21 reviews)

Peaceful Cape Cod retreat, 1.5mi to National Seashore

Orleans

7% off
S$6,643
for 7 nights, 1 home
S$949 per night
includes taxes & fees
Peaceful Cape Cod retreat, 1.5mi to National Seashore
Private kitchen
Exterior
entrance to mallardview
Interior
Exceptional
(60 reviews)

5 bedrooms ocean view estate overlooking cape cod bay

Orleans

8% off
S$10,208
for 7 nights, 1 home
S$1,458 per night
includes taxes & fees
5 bedrooms ocean view estate overlooking cape cod bay
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

6% off
S$2,899
for 7 nights, 1 home
S$414 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Outdoor dining
Marina
Exterior
Pine Room/Family room with queen pull out couch
Exceptional
(43 reviews)

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

South Dennis

7% off
S$1,754
for 7 nights, 1 home
S$251 per night
includes taxes & fees
Rates just lowered for last week of July and Aug with 5 night min accepted.
Interior
Deck with teak table and chairs
Kitchen with island
Living room with cathedral ceiling - open floor plan
Exceptional
(90 reviews)

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

Chatham

7% off
S$4,865
for 7 nights, 1 home
S$695 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Fire pit & couch
Center island with seating for 4
Pool house
2000+ SF multi level patio, pool, pool house, outdoor kitchen, fire pit & more!
Exceptional
(43 reviews)

Chatham Loop/Stage Neck/5 Bed/6 Bath

Chatham

8% off
S$12,299
for 7 nights, 1 home
S$1,757 per night
includes taxes & fees
Chatham Loop/Stage Neck/5 Bed/6 Bath
The Woolrych House sits above a private Brewster beach.
Outdoor dining
View of the Woolrych House during low tide.
Dinner with a view.
Exceptional
(50 reviews)

Picturesque Private Beachfront House on Cape Cod Bay

Brewster

8% off
S$6,209
for 7 nights, 1 home
S$887 per night
includes taxes & fees
Picturesque Private Beachfront House on Cape Cod Bay
Updated Kitchen for Summer 2020
Fully equipped
Outdoor dining
Seating for 3 at kitchen counter
Living room has vaulted ceiling, skylight & ceiling fan. Central AC
Exceptional
(55 reviews)

3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.

South Dennis

12% off
S$4,889
for 7 nights, 1 home
S$698 per night
includes taxes & fees
3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.
Living area
Private kitchen
Exterior
Interior
Exceptional
(10 reviews)

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

Dennis

7% off
S$3,821
for 7 nights, 1 home
S$546 per night
includes taxes & fees
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Second floor front bedroom with view of Cape Cod Bay
Living room looking toward front / first floor front bedroom door
Kitchen
Outdoor dining set overlooking the bay on deck
Exceptional
(28 reviews)

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

Eastham

6% off
S$4,614
for 7 nights, 1 home
S$659 per night
includes taxes & fees
Waterview, 4 BR, 100 Feet from Private Eastham Bayside Beach!
Living area
Outdoor dining
Dining
Exterior
Exceptional
(29 reviews)

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

Eastham

7% off
S$4,371
for 7 nights, 1 home
S$624 per night
includes taxes & fees
Sun-filled, renovated house within minutes walk to private bay sides beach.
Outdoor firepit
Loft living room
Modern cape architecture
King bed in primary suite
Exceptional
(6 reviews)

Modern beach house, steps to private beach, perfect for groups!

Eastham

10% off
S$4,042
for 7 nights, 1 home
S$577 per night
includes taxes & fees
Modern beach house, steps to private beach, perfect for groups!
Property grounds
Private kitchen
Living area
Outdoor dining
Exceptional
(5 reviews)

Adorable updated Cape in East Orleans!

Orleans

7% off
S$6,379
for 7 nights, 1 home
S$911 per night
includes taxes & fees
Adorable updated Cape in East Orleans!
Study/Lounge are with water views
Dining room with water views
Living area
Terrace/patio
Exceptional
(35 reviews)

Steps to Paine's Creek-The Perfect Vacation Home

Brewster

7% off
S$5,268
for 7 nights, 1 home
S$753 per night
includes taxes & fees
Steps to Paine's Creek-The Perfect Vacation Home
Private kitchen
Living area
Exterior detail
Room
Exceptional
(27 reviews)

Steps to the beach!

Dennis Port

7% off
S$3,351
for 7 nights, 1 cottage
S$479 per night
includes taxes & fees
Steps to the beach!
Exterior
Welcome to the porch where you can relax after a day at the beach or golfing!
Built in microwave and range.
Eat in kitchen. Enjoy the lobsters!
Wonderful
(65 reviews)

Delightful Cottage for Two

Chatham

7% off
S$2,192
for 7 nights, 1 cottage
S$313 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)
  • First Encounter Beach (1.9 mi / 3.1 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)

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?
If you're planning a break in Orleans, East Orleans is one of the most popular locations to stay. Whatever your style of travel, Vrbo is bound to have a holiday rental here that's right for you.
What is the most popular type of holiday rental accommodation in Orleans?
The most popular types of holiday rentals in Orleans are houses. Want something different? Vrbo offers a variety of options to match the diverse needs of our guests, so you'll see properties in all shapes and sizes. The ideal fit is waiting for you — get hold of yours today.
How much does it cost to rent a holiday rental in Orleans?
Property type, length of stay and season are some factors that can determine the price of a holiday home. Simply add your travel dates to find your perfect escape. From cosy country cottages to expansive villas, all Vrbo holiday rentals offer terrific value.
How much does it cost to rent a beach house in Orleans?
Prices for beach houses in Orleans vary depending on the style and size of the property and when you're travelling. Just enter your travel dates into Vrbo and how many guests to view your holiday rental options and prices. From there you can use the filters to tailor your search results by amenities, nearby activities, ratings and more.
Are there pet-friendly holiday rentals in Orleans?
Pack up a suitcase for the pooch in your life because Orleans has 286 properties that throw out the welcome mat to doggie guests. Let your happy hound enjoy the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your destination and travel dates, then check the "Pets allowed" filter box.
Can I rent a house with a pool in Orleans?
Pack your swimwear and inflatable swan, because there are 36 houses with a private pool in Orleans. Stay at one of these superb holiday homes and let every day be a pool day. Simply enter your dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Orleans?
Some of the most popular rental amenities people search for in Orleans include a garden, a firepit and an ocean view. Whether you're holidaying with pals, family or even pets, Vrbo holiday rentals provide the best amenities for chilling out with the people who matter most.
Are there large group holiday rentals in Orleans?
With 81 properties that can host 10 people or more in Orleans, you won't have to leave anyone off your guest list. From extended family holidays to events like weddings and birthday parties, Vrbo can help you find a large group rental to suit the occasion.
Are there holiday rentals in Orleans that welcome kids?
Bring the whole family together for fun-filled adventures in Orleans at one of our 286 family-friendly properties. These stays feature amenities that are ideally suited to getaways with the kids, such as kitchens, bunk beds and pools. Simply check the "Properties good for families" filter and pick your favourite.
What are the top attractions for families in Orleans?
There are tons of fun things to see and do with the family in Orleans, such as:
  • Nauset Beach
  • Skaket Beach
  • Marconi Beach
Are there one-bedroom holiday rentals in Orleans?
Orleans has seven one-bedroom rentals on offer. Usually located in popular areas thanks to their smaller size, a one-bedroom holiday rental is great if you're travelling with a friend or your partner. And with home comforts like full kitchens and more privacy than a standard hotel, you'll be able to kick back and relax while discovering this amazing destination.
Can I find two-bedroom holiday rentals in Orleans?
Orleans has 36 two-bedroom holiday rentals for you to select from. Go for a holiday home with all the space and comfort you're looking for at a price that won't break the bank on Vrbo.
Are there holiday rentals with WiFi in Orleans?
Whether you'd like to stay in touch with the news, look over emails or surf your social networks, there are 87 holiday homes with WiFi in Orleans. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Orleans?
Choose from 269 holiday rentals with air conditioning in Orleans giving you that cool, cool breeze and extra bit of comfort. Just enter your travel dates and then take advantage of our filter tool to help you find stays with air conditioning.
How old do you have to be to rent a holiday rental in Orleans?
We recommend you check with the Orleans holiday property you want on Vrbo as the minimum age varies. However, normally it's 16, 18 or 21.
How long can I rent a holiday rental in Orleans for?
How long you can rent a holiday rental in Orleans differs according to the property. Just enter your selected travel dates to display a list of options offering extended stays. With a range of amenities such as kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to find a perfect place to call your home away from home in Orleans.

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