Family-friendly holiday rentals in Orleans

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.

Private Bay Beach and Sunset Views! Dog friendly.

The beauty of Cape Cod awaits in this meticulous cottage with water views. Access to a private bayside beach is just steps away, across from the driveway and down a short sandy path. Beach chairs and beach towels included. Ride or walk 1 mi away to a great bike trail, or to National Seashore beaches, shops and restaurants. Or, relax at the cottage with updated amenities, appliances, comfortable beds, and a wonderful outdoor space with deck, fire pit, outdoor shower, lawn games and a hammock!

Romantic Cape Cod Tiny House + Hot Tub

Welcome to the Romantic Hideaway, our magical, secluded tiny house nestled between lush gardens and the woods alongside our property. Just a short drive to ocean beaches and freshwater ponds, and a pleasant walk to the quaint center of Wellfleet. Wake to birdsong and enjoy fresh muffins on your sunny, private deck. Your stay includes access to our Magnolia Spa with hot tub and sauna (June+); massage is available in July at special guest rates. A sweet, quiet escape on the Outer Cape.

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

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 offering picturesque views of the Town Cove. Guests are encouraged to bring their kayaks and paddleboards, as a town landing is conveniently located nearby. Nestled on a tranquil road, Snowtop is just 3 miles from stunning Nauset Beach and 2 miles from the center of Orleans.

1850 Orleans Antique Home with Path to Arey’s Pond

Make memories at this private family and pet-friendly 3 BR Orleans antique Cape Cod home with access to Arey’s Pond. Kayak and paddle-board directly to Little Pleasant Bay and beyond. The property was once home to the town tavern on Old County Road en route to Orleans. Enjoy the wrap-around 3 season porch. Antique home with bath and other renovations that were recently completed. We want to share this unique property with those who appreciate the history. Please ask questions!

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.

Cape Cod Heaven

Private one bedroom with full bath and balcony overlooking garden and a peek at the bay. Great location less than a mile from beautiful First Encounter Beach, a wonderful bay beach, and five minute walk to freshwater pond with sandy beach. Ocean beaches and bike trail close by. Bring your bikes or kayaks, or rent them, and enjoy all the Cape has to offer. Great for singles, couples, small families. Has a small refrigerator, microwave and Keurig. There is not a kitchen.

The Sea Captain's Carriage House

The 1840s Carriage House has been beautifully remodeled. The first floor has a living room, dining area, kitchen, and powder room with washer/dryer. The backyard deck has seating for four and a Weber gas grill. Upstairs, the large, elegant bedroom features a king-sized bed, sitting area, reading nook/twin bed, writing desk, and ensuite bathroom with shower. The half acre property offers beautiful gardens for you to enjoy and a delicious outdoor shower.