Kid-friendly holiday rentals in Orleans

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Popular amenities for Orleans kid-friendly rentals

Child-friendly house rentals

Top Guest favourite
Home in Orleans
5 out of 5 average rating, 64 reviews

Cape Cod Charmer

KarenRating, 5 stars8 months ago
Felt like home to us! Wonderful week stay! Just like the previous two year’s stay! We love this home!
Guest favourite
Home in East Orleans
4.91 out of 5 average rating, 11 reviews

Orleans, MA Luxury Getaway

JoshRating, 5 stars3 weeks ago
We had a wonderful stay at Sam’s place. Very close to a bunch of good restaurants and very accessible to the entirety of the cape. Couldn’t recommend more highly. Sam was an excellent host.
Superhost
Home in Eastham
5 out of 5 average rating, 3 reviews

Sweetbriar ~ Charming Cape Cottage ~ Dog-Friendly!

KarlRating, 5 stars1 day ago
We had a great time. Although the weather did not let us get to the beach. There was a lot to do. Quick 30 minute ride to Provincetown. Cottage was more than enough room. Tea kettle and k cup coffee maker were perfect. Cozy and warm. Didn’t need the air conditioners since it was only 60 degrees but a great option. We would love to do this again. Host was proactive and very responsive to any questions. Thank you Andrei.
Superhost
Home in Orleans
4.92 out of 5 average rating, 26 reviews

5-bedroom Cape with a pool and yard games.

CatherineRating, 5 stars9 months ago
We enjoyed our stay very much ~ the house and large fenced yard w/deck (perfect for pup) are amazing & the hosts were very kind, accommodating & responsive. The location was great with a short ride to local beaches and/or Chatham for a fun day of shopping or night out. The host’s welcome basket with treats & seltzers were a great surprise after a long day of travel. We loved playing ping pong in the garage! I do suggest the listing bedroom descriptions & photos be updated as we were pleased to find a king bed in the master BR (vs the queen shown) and a full bed (vs the twin) in the downstairs guest-room. Perhaps renovations are underway so we were pleasantly surprised! The only improvements I would suggest are adding a screen door to the deck & heat for the pool, having more wine glasses (the kitchen was wonderfully stocked otherwise), & adding amenities like blankets, washcloths, a hair dryer, beach/pool towels & chairs (we brought our own). We hope to be back next year!!
Superhost
Home in Eastham
4.96 out of 5 average rating, 26 reviews

Stunning Cape Cod Escape

ErikaRating, 5 stars8 months ago
Beautiful, clean home in a great location to explore everywhere on the cape! Excellent communication with Rhonda. We would definitely stay again in the future!
Top Guest favourite
Home in Harwich
4.93 out of 5 average rating, 46 reviews

Waterfront★ Pvt Beach ★ On Bike Path ★Bikes★Kayaks

DesireeRating, 5 stars2 days ago
Aruna's cottage was even more beautiful, both inside and out, than the photos. The interior was gorgeous, light filled and many decorative touches that made it feel like a 5-star hotel. The furniture was comfortable and there were many lamps which made reading in the evenings very easy. The art TV picture was very nice when the TV wasn't on rather than looking at a big, black screen. We used the dining table with statement chandelier for all our meals. There were all the kitchen pots, pans and utensils we needed. The refrigerator ice maker and water features were appreciated. Both showers were outstanding in function and beauty. Everything was spotless. The patio was so comfortable with a huge umbrella to shade us while we enjoyed the lake view which was ever changing. A highlight was when a huge turtle came out of the lake and walked across the yard. The Cape Cod Rail Trail is just off the property and is screened by a beautiful, tall white fence and evergreens.
Top Guest favourite
Home in Chatham
5 out of 5 average rating, 160 reviews

Chatham Charmer

PhilRating, 5 stars2 weeks ago
A lovely home with plenty of space, well equipped for a couple or family with young children. The bed was huge, and so comfortable! Comfortable lounge for chilling out in front of the big smart TV, good kitchen with modern appliances. We made use of the gas grill for BBQ, and it was great to have the 2 bikes available to use, with the cycle trail 2 minutes away. Chatham is a great location, a lovely main street, restaurants and shops, 20 minute walk away or a short drive with plenty of parking. We'd recommend "Pain d'Avignon" for great coffee, and lovely bistro food for lunch. Great communication from Godelieve from the moment we booked, good information in advance, through check-in. Responsive and helpful with any small queries. We had a lovely time, thank you, we'll be back.
Top Guest favourite
Home in East Orleans
5 out of 5 average rating, 71 reviews

4 Season Cottage, Nauset Beach, tennis court

AbigailRating, 5 stars1 week ago
A dreamy Cape Cod getaway. If you have the privilege of staying here please take full advantage! The surroundings alone are stunning. Ken ensured the actual space is designed for your comfort & leisure. The kitchen was well-equipped and clean. The outdoor& indoor showers were great too. If I hadn’t just had neck surgery we would have taken full advantage of the pickleball court. I could go on and on about how special this place is!

Kid-Friendly apartment rentals

Guest favourite
Apartment in North Eastham
4.91 out of 5 average rating, 268 reviews

Eastham Escape

BruceRating, 5 stars1 week ago
My son and I had a wonderful weekend visit to Eastham. Min's place was very clean, comfortable, and cosy. Coffee bar was well stocked and much appreciated!
Guest favourite
Apartment in East Dennis
4.86 out of 5 average rating, 155 reviews

Peace By The Bay

RichardRating, 5 stars1 month ago
Bill and Trish were amazing hosts, and they made sure the place was exceptionally clean. They even had fresh flowers for us when we arrived.
Superhost
Apartment in Eastham
4.89 out of 5 average rating, 107 reviews

Peaceful retreat in the woods...

KatieRating, 5 stars1 week ago
Mary's place was amazing! It had everything we needed for a long weekend on the Cape. The space is private, and very quiet, which was nice. We loved being tucked in the trees. Plenty of space for our bikes outside too. Mary was very friendly and welcoming, and we felt right at home. We would definitely stay again!
Top Guest favourite
Apartment in Wellfleet
4.96 out of 5 average rating, 190 reviews

Beautiful Creekside Apartment in Wellfleet Center

BenRating, 5 stars1 week ago
Beautiful little condo with great views and everything within walking distance. The photos do not do it justice! Will definitely be back and would recommend for anyone looking for a relaxing vacation on the cape
Guest favourite
Apartment in Provincetown
4.96 out of 5 average rating, 406 reviews

Cozy 3rd Floor Apartment with a View

SarahRating, 5 stars2 weeks ago
We had a fantastic stay at Peter’s place! It exceeded expectations in terms of cleanliness and decor - very cozy! The apartment also was perfectly situated on the main street near lots of restaurants and shops. Peter was a great host and very responsive - highly recommend!
Top Guest favourite
Apartment in Chatham
4.97 out of 5 average rating, 263 reviews

The Knoll

ZackRating, 5 stars1 week ago
Peg’s home was perfect for our stay in Chatham. It was quiet and peaceful but close enough to Main Street and everywhere we would want to go during our visit.
Guest favourite
Apartment in North Eastham
4.88 out of 5 average rating, 266 reviews

Cape Cod Suite Near Private Beach

KristinaRating, 5 stars1 day ago
Spent a wonderful weekend at Arthur’s with a friend. Eastham is a great home base for Ptown, Wellfleet, Truro, Chatham, and all the rest the Cape has to offer. Arthur’s place was the perfect size for us two ladies, the beds were exceptionally comfy, and the surroundings couldn’t be better. Arthur is a gracious host who greeted us warmly then gave us space to enjoy.
Guest favourite
Apartment in Brewster
4.85 out of 5 average rating, 125 reviews

Hip Studio Area, Skylights & Moonbeams

ManlioRating, 5 stars21 months ago
Nice and very comfortable and quiet area.

Child-Friendly Holiday Condos

Guest favourite
Condo in Provincetown
4.97 out of 5 average rating, 216 reviews

P-Town Beach Beauty on the Bay. Water View!

OctaviaRating, 5 stars1 week ago
Rob was a great host ! He responded within a timely manner and the place was very clean and felt just like home. I would suggest bringing board games and such for the rainy days. For the folks who enjoy cooking the kitchen was fully stocked with everything you need. I would also recommend renting bikes or taking an Uber if you don't like walking. The walk to town was about 25 minutes. Overall great stay would love you stay her again it gives you the peace and quiet while also being close enough to everything and a beautiful view of the ocean.
Guest favourite
Condo in Brewster
4.97 out of 5 average rating, 180 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

JeremyRating, 5 stars2 weeks ago
Anna’s place was exactly what we needed to have a peaceful and relaxing Memorial Day weekend stay. We knew the weather might be on the cooler side, so purposefully wanted to stay where there was the possibility of using the indoor pool – the sponsored guest passes were a huge benefit here, and Oceans Edge staff even went above and beyond, adding an extra day to our pool access since we were picking them up so late in the day. The condo was clean and filled with all the essentials, in a very quiet area of the property. Would definitely stay again!
Guest favourite
Condo in Chatham
4.86 out of 5 average rating, 103 reviews

Steps to Private Beach in Chatham

IsaacRating, 5 stars3 weeks ago
Great location for a quiet, peaceful Cape Cod family getaway. Perfect space for group of 4, located on quiet corner of Chatham/cape cod. Very walkable to downtown and lighthouse beach (best beach in cape cod). Julia is a wonderful host, extremely responsive and her local recommendations for visitors were outstanding, especially for first time visitors to CC. Would recommend.
Top Guest favourite
Condo in Provincetown
4.97 out of 5 average rating, 148 reviews

Bargain: July 5 Week: Waterview In Heart of Ptown!

MarkRating, 5 stars1 month ago
Alan's place was a perfect home base for our Provincetown getaway. Checking in/out was a breeze, we found the condo clean and lovely and the location cannot be beat. We would definitely stay here again - thank you!
Top Guest favourite
Condo in Dennis Port
4.86 out of 5 average rating, 204 reviews

The 5 minute walk to beach Super Cute Beach Condo

KristaRating, 5 stars1 week ago
Great place to stay. Close to the beach and also easy to drive from to hit major spots along the Cape Cod bay. Sam provided some good local recommendations and we loved our stay!
Guest favourite
Condo in Provincetown
4.89 out of 5 average rating, 187 reviews

Bayshore 2:Direct waterfront/Parking/Pets welcome

WendyRating, 5 stars2 weeks ago
This is an easy place to stay. The kitchen is super well equipped, and a great refrigerator, comfortable place to be in, really great location and view. Thank you so much!
Top Guest favourite
Condo in Chatham
4.96 out of 5 average rating, 332 reviews

In-town, Pied-a-Terre. Private, Sunny Urban Oasis

JessieRating, 5 stars2 days ago
We loved Tony’s place! A bit off the beaten path but very walkable to the main strip and centrally located on the Cape. The instructions and photos were very helpful, & the space was immaculately clean and just as described. We’d definitely stay again if we find ourselves back in Chatham!
Guest favourite
Condo in Brewster
4.88 out of 5 average rating, 253 reviews

Shining Sea Condo

SpencerRating, 5 stars3 days ago
Courtney was an amazing host! Her place was beautiful and clean. I would definitely stay again! Check this place out it’s perfect!

Quick stats about holiday rentals that are kid-friendly in Orleans

  • Total rentals

    80 properties

  • Nightly prices starting at

    $92 AUD before taxes and fees

  • Total number of reviews

    2.8K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

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