Holiday houses 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.

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property

Steps to Rock Harbor, Cozy Fully Renovated Cottage

Welcome to Rock Harbor! Nestled just steps from the picturesque Rock Harbor in Orleans, our newly renovated Cape Cod cottage offers the perfect blend of coastal charm and modern comfort. Ideally located between the vibrant villages of the Mid Cape and the natural beauty of the Outer Cape, it’s a great home base for day trips to Provincetown, the Cape Cod National Seashore, and local favorites like Chatham and Hyannis. Perfect for families, friends, or couples seeking a relaxing getaway.

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.

Sophisticated, Private Cape Cod living

LOCATION: 3/4 mile off main road (unpaved road). Located on the town line of Brewster and Orleans with less than 5 minutes to Chatham or Harwich by car. Nauset and Skaket beaches are less than 3 miles away. Nickerson state park less than 1 mile away. Cape Cod National seashore is located within 7.2 miles of our property. Shopping on Main Street in Chatham is 15 minutes. Enjoy a nice, tranquil walk, listen to the birds or feast your eyes on the surrounding conservation land.

Shining Sea Condo

Ocean Edge Condo with cathedral ceilings! Beautiful private deck located on the 5th hole of the Ocean Edge golf course! Located within Eaton village. TWO KING beds, along with pullout couch allows 6 to sleep comfortably. Linens are included!! Large kitchen with washer/ dryer, AC units and heat throughout the entire unit. Wifi and THREE smart TVs with ROKU devices. Flexible dates allows guests to stay whatever length they would like instead of a mandatory week. Come enjoy!

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.

Beachfront Cottage on White Pond (Marshmallow)

Our Cottage sits directly on White Pond tucked away on acres of private property. Our cottage offers a private beach, deck, outdoor shower, outdoor dining area all while enjoying Cape Cod. White Pond is ideal for swimming, boating and fishing. The bike path and well known beaches are less than 2 miles and near to many delicious restaurants. There is another cottage on this property that sleeps four if you have other guest wanting to join

Cozy Condo/Cottage on Cove, Walk to Town

Welcome! Enjoy a Fabulous 180 degree water view out our master bedroom and living room. Walk to Orleans village, art galleries, restaurants & shopping. Bike to Beaches and baseball all within a mile. One floor condo is good for couples, solo adventurers, small families. One full bath with shower and one half bath, plus a new outdoor shower. Master BR has Queen bed. Second BR has a queen bed with a twin trundle pull out.

The Salt Pond Cottage

This is a free-standing private cottage that sleeps 2 comfortably. A spiral staircase leads up to a sleeping loft with a NEW QUEEN size Nectar bed! There is a full futon couch on the main level. The kitchen has everything you may need. The most spectacular thing about this home is its close proximity to the National Seashore. The salt pond, bike path, and freshwater ponds are also moments away!

Cozy Waterfront Apartment, Private Beach Access

Charming living space with nautical decor invites you to unwind off the grid for a few days. There is a window seat for reading, small high top for morning coffee, and all the accessories for a relaxing day at the beach. A five minute drive into town for local shopping and dining. Many scenic trails for walking and biking. Make us your base as you explore Cape Cod’s beautiful shores!