Top 10 Vacation Rentals In Orleans, Massachusetts - Updated 2024

Sakshi
Sakshi  
Updated
| 5 min read

Nestled in Barnstable County, Orleans is a quaint town that is famous for its beautiful beaches, shops, and delicious seafood restaurants. Orleans is home to Nauset Beach, Skaket Beach, and several smaller beaches within the town. Visitors can enjoy plenty of activities such as swimming, sunbathing, kayaking, and windsurfing while here. Orleans is also home to Cape Cod Baseball League for college players. Adventure seekers will surely love exploring Cape Cod Rail Trail and marveling at the beauty of nature. For those looking to do some shopping, downtown Orleans is home to many unique shops and boutiques. So whether you’re looking for a relaxing vacation or an action-packed getaway, read on for a list of the top vacation rentals in Orleans, Massachusetts.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 13, 2024.

1. Charming cottage with lovely deck (from USD 200)

This charming cottage is within walking distance of Bakers Pond, which is perfect for swimming, fishing, or kayaking. The kitchen is fully equipped with all the essentials, and there’s even a washer and dryer for your convenience. The living room is complete with an electric fireplace and TV, ideal for spending quality time after a long day exploring the nearby beaches.

Outside, there’s a lovely deck perfect for enjoying the fresh Cape Cod air. Moreover, it’s pet-friendly, so you can bring one furry friend along for the trip.

Stayed at this property?
Orleans, Massachusetts, United States
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
really nice big deck with excellent table and chairs where we ate all our meals
everyone had their own space and the common areas were very comfortable
it is in need of some upgrades to make a stay a bit more comfortable and appealing
Cleanliness:
neat and clean just as advertised
very clean and well equipped for renters
clean accommodations with everything you need for a week-long stay with a family and a pup
the house was clean convenient and the owner judy was very attentive and helpful
Host:
she was very helpful
judy was a perfect host
she was also extremely responsive and quick to recommend restaurants
top notch judy is awesome and attentive
the owner does provide linens and towels which is very nice
Location:
baker's pond is very close by and a great place to go for a swim
the location of this house is perfect in my opinion
Read more reviews
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2. Pet-friendly home with sun porch (from USD 260)

This lovely home is just a short walk from Nauset Beach, making it the perfect spot for summer fun. The sun porch is the perfect place to relax after a long day at the beach, and the fire pit is great for roasting marshmallows or simply enjoying the night sky. The dartboard is also a great way to entertain guests of all ages. This rental is pet-friendly, so you can bring your furry friend along for the vacation!

Stayed at this property?
Orleans, Massachusetts, United States
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 1 Bathroom

Top guest reviews
Amenities & Room:
the kitchen was well-equipped and having the grill was great
Location:
it is so close to nauset beach and many orleans attractions
the house was in a good location with easy access to nauset beach and a short drive from town
Read more reviews
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3. Comfy studio close to Nauset Beach (from USD 225)

This cozy little studio is the perfect place for a romantic getaway or a solo adventure. It’s just a five-minute walk from Nauset Beach and has a small kitchenette for preparing meals. And, since it’s so close to the beach, you’ll have plenty of opportunities to enjoy the sun and sand.

There’s also a TV and Wi-Fi, so you can stay connected during your stay. There’s also a small patio area with a table and chairs perfect for enjoying the summer weather.

Stayed at this property?
Orleans, Massachusetts, United States
Apartment 3 Guests 1 Bathroom

Top guest reviews
Amenities & Room:
one review hit the wifi we found a router in the room with a strong signal
dark furniture (paint it white?) and super outdated bathroom fixtures
positives: short walk to beach comfy beds beach chairs provided easy check in/out process
Cleanliness:
the room is bright clean and upbeat
it was clean had a well stocked kitchenette and the bathroom is small but pretty and modern
clean well maintained and close to the beach
the property was clean close to the beach and exactly as listed
Location:
loved being so close to the beach while in a totally residential neighborhood
so many small nice touches and so close to the beach
cute little getaway house very clean 5 minute walk to a beautiful beach
really lovely room new bathroom close to the beach
walking distance close perfect if you need a place to hang your hat
Read more reviews
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4. Fully furnished cottage near Bakers Pond (from USD 232)

This pristine cottage in Orleans is the perfect summer getaway! The living room is spacious and features a comfortable sofa including a TV for watching movies or shows. The kitchen is fully equipped with all the amenities you need to prepare your meals. Moreover, this charming cottage has an outdoor shower that is perfect for rinsing off after a day at the beach.

The property is just a short walk away from Bakers Pond, where you can go swimming, fishing, or kayaking.

Stayed at this property?
Orleans, Massachusetts, United States
PRIVATE VACATION HOME 5 Guests 2 Bedrooms 1 Bathroom

Top guest reviews
Amenities & Room:
a/c units work great
the cottage was welcoming fully equipped and oh so comfortable
the cottage is well appointed and comfortable on every level
Cleanliness:
great little super clean cottage with so many unexpected extras
the place itself was very clean cute and the kitchen was well stocked
the space is clean comfortable well-equipped and is exactly as pictured
the cottage was spotless and comfortable
the cottage is adorable and very clean
Host:
the owners made us feel very welcome
the owners were very easy to reach with any questions we had
the hosts were also very nice and responsive
the hosts are exceptionally responsive
the owners were very easy to communicate with and punctual
Location:
the location is great
it was a good location for exploring cape cod
really amazing locations to walk/run/bike
great location and wonderful hosts
the property was in a beautiful spot on a street conveniently located right off of 6a
Read more reviews
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5. Ideal vacation rental with large deck (from USD 180)

Whether you’re looking to relax or stay active, this is the perfect rental for your next vacation in Cape Cod. This holiday home has a large deck with plenty of seating, perfect for enjoying the outdoors. The upper floor of the home has everything you need, from a spacious living room with plenty of natural light to a full kitchen with modern appliances and a cozy dining area.

You’ll also have access to Wi-Fi and a foosball table, making it easy to stay entertained. And with multiple bedrooms, there’s plenty of space for everyone to spread out and relax. Plus, the location is ideal - you’ll be close to town but have plenty of privacy.

Stayed at this property?
Orleans, Massachusetts, United States
PRIVATE VACATION HOME 5 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
overall loved the space but for a sleeps 8 i expected more seating in the living room
overall loved the space but for a sleeps 8 i expected more seating in the living room
Cleanliness:
beautiful private home clean and a well stocked kitchen
beautiful private home clean and a well stocked kitchen
spacious modern and stylish clean
the home itself is lovely and was very clean upon our arrival
Location:
beautiful space close to all the great things orleans and the cape has to offer
Read more reviews
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6. Quaint home with spacious living room (from USD 286)

This quaint home is situated in a quiet neighborhood, yet it’s still centrally located near some of the best beaches in Orleans, making it the perfect spot for sun-seekers and water lovers. The living room is spacious and has a large flat-screen TV, perfect for relaxing after a long day of exploring everything that Cape Cod has to offer! WiFi is included so you can stay connected while on vacation. There is also a washer and dryer available for use.

The deck has outdoor furniture and a gas grill, so you can enjoy the outdoors.

Stayed at this property?
Orleans, Massachusetts, United States
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
two king beds and one queen bed were all excellent and comfortable
outdoor shower and great deck out front as well
central air was a great perk and the kitchen was amply stocked with everything we needed for cooking
great room was perfect for hanging out cooking eating
Cleanliness:
it was clean and surprisingly spacious
the house was clean and spacious
it was clean spacious and was tastefully decorated
spacious nice bathrooms everything on one floor convenient and clean
Host:
the owner very helpful
the owners were very accommodating and easy to contact
art and meredith were wonderful hosts
very kind thoughtful and helpful rental property owners who live next door
it was very easy to communicate with the owner
Location:
the location in orleans was ideal
great property close to all attractions
good central location for orleans downtown shops and restaurants
we found the location was great we were just a few minutes drive from 2 beaches
great location in orleans yet set back on a quiet street
Read more reviews
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7. Fully equipped cottage with spacious garden (from USD 325)

This cottage is the perfect place to relax and enjoy all that Nauset Beach has to offer. It is fully equipped with everything you need to cook meals, including a full kitchen with all the necessary appliances. The living room is comfortable and spacious, with plenty of seating for everyone. The bedrooms are cozy and inviting, with soft beds and plenty of storage space.

There is a washer and dryer so you can keep your clothes clean during your stay. Moreover, there is a sunlit deck as well as a spacious garden perfect for al fresco dining.

Stayed at this property?
Orleans, Massachusetts, United States
45 reviews   Superhost Wifi Available
Entire cottage 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the cottage was very cozy with a great back deck
newly updated outdoor shower… new beach chairs very nice deck for outdoor dining
the mattress in the master bedroom is easily the most comfortable mattress we’ve ever experienced through an airbnb
an easy walk to beautiful beach and dunes and very well set up — kitchen needs beach chairs etc
the king sized bed in the master bedroom was very comfortable
Cleanliness:
clean and comfortable home in quiet location
cottage is very nice clean and well maintained
Host:
nancy was super responsive to any questions we had
nancy was easy and friendly to communicate with very helpful and quick to respond
Location:
best location on the cape
it's an excellent location and we lucked out with great weather
great for am + pm walks and literally a minute walk to the water
it was great being able to walk to nausett beach from the house
ideal location if you enjoy short walks to salt marsh and ocean trails
Read more reviews

8. Beautiful rental with private beach (from USD 160)

This comfortable rental boasts its own private beach, allowing you to enjoy stunning ocean views and listen to the waves crash from your porch. With trails nearby, you can explore the area and take in the gorgeous surroundings. There is a smart TV and Wi-Fi available to keep you entertained while you are indoors.

The patio space at the cottage is perfect for enjoying the beautiful weather. There is a table and chairs for dining al fresco, as well as a gas grill for cooking up your favorite summer meals.

Stayed at this property?
Orleans, Massachusetts, United States
201 reviews   Superhost Wifi Available
Entire guest suite 3 Beds 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
lovely view from the main room
well appointed mini kitchen comfortable beds thoughtful use of space and nice touches like a basket of snacks
the private beach view of the water beautiful gardens comfortable and clean accommodations were perfect for our family’s vacation
the kitchen is nicely equipped with toaster oven and microwave
many thoughtful touches made our stay comfortable and homey
Cleanliness:
it was very clean and quiet
the apartment is clean bright large and comfortable
secluded and quiet private beach setting super comfortable clean and safe setting
very clean well stocked and easy access to a beautiful little private beach
the place was very clean and the flowers/landscaping were breathtaking
Host:
melody was a wonderful host
melody was an awesome host
melody is the perfect host
melody is a great host
melody was a great host and very personable
Location:
the location is really special
absolutely gorgeous location and wonderful spacious accommodations
it is close to some outstanding restaurants from local breakfast places to 5-star resort restaurants
great location to explore the beauty of cape cod
a great location on the cape- near to town and beaches yet quiet and beautiful view
Read more reviews

9. Cool and airy rental near restaurant and shops (from USD 400)

If you’re looking for a peaceful and quiet place to stay on your next vacation, look no further than this charming rental located in a serene neighborhood in Orleans. Places like Skaket Beach, Rock Harbor, and Rock Harbor Grill, amongst other entertainment and dining areas, are nearby. Complete will all essentials, this house provides guests with an HDTV with streaming facilities and continuous Wi-Fi throughout their stay.

In the morning, you can relax while enjoying a cup of coffee in the garden. If you’re feeling more adventurous, hop on your bike and explore the bike trail that winds its way through the neighborhood, a mere 0.8 km (0.5 mi) away.

Stayed at this property?
Orleans, Massachusetts, United States
58 reviews   Superhost Wifi Available
ENTIRE HOME 7 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
nice space with lots of room to relax
the house is very comfortable with a well-stocked kitchen for cooking
beds were comfortable
Cleanliness:
very clean and well appointed house
amazing house everything was very clean and organized
jeff & colleen’s place is spacious clean and well-appointed
the property is beautiful extremely well-appointed and spotlessly clean
it was as pictured when we arrived well decorated and very clean
Host:
the hosts were excellent communicators
hosts were very responsive as well
hosts were always very responsive and easy to reach
we had the best time and the hosts were fabulous
Location:
great location close to everything you need for a great cape vacation
this lovely house is close to town and bike path which is convenient
nice place to stay for the weekend very close to many restaurants
beautiful location close to a lot and a very peaceful porch out back
neighborhood is also nice and quiet
Read more reviews

10. Spacious accommodation with pool (from USD 1560)

Nestled in the heart of East Orleans, this home is close to all the best that Cape Cod has to offer, including shopping, dining, and of course, the beach! There is plenty of room at this rental for your whole group to spread out and relax. The kitchen is complete with high-end appliances and granite countertops.

This home also features a beautifully landscaped yard with a heated pool and a hot tub ideal for relaxing after a long day at the beach.

Stayed at this property?
Orleans, Massachusetts, United States
PRIVATE VACATION HOME 20 Guests 8 Bedrooms 9 Bathrooms

Top guest reviews
Amenities & Room:
the pool was perfect as was the fire pit and grill
Cleanliness:
the house is beautiful and clean and has everything you need with wonderful location near food and beaches
Host:
we couldn’t have asked for more sean was a gracious and attentive host welcoming and responsive within minutes
Location:
our family loved the location and the attention to every detail
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

Enjoy a relaxing vacation in Orleans

Orleans, a beautiful town in Barnstable County, is an amazing tourist destination since it is home to gorgeous beaches and stunning natural parks. Book your accommodation from this list of top vacation rentals In Orleans, Massachusetts, today!

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Sakshi Agarwal, a respected professional writer, specializes in creating articles, particularly those related to travel. She excels in tailoring her writing to suit any audience and is adept at...Read more

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