Holiday houses in Orleans

Walk to Lake! A/C, Private BackYard/FirePit/Games!

➤ Relax by the Outdoor Fire, stay in for a Family Movie Night, or explore Orleans’ nearby Beaches/Shopping/Dining ➤ Central: ★ Walk to Pilgrim Lake ★ 5mins drive to Beaches/Shopping ➤ Nestled in the peaceful windswept woodlands of the Lower Cape, this bright & spacious home is the ideal place for calm, connection & conversation ➤ A favorite of Family Holidays, Friends groups & Freelancers, this recently-renovated Orleans acreage transports you to a simpler time-where stress is left behind.

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.

Magical Writers Cabin + hot tub in Wellfleet Woods

Escape to our unique Writer’s Cabin in the peaceful woods of Wellfleet—a magical retreat that feels like you're staying in a treehouse! You'll be surrounded by nature yet just minutes' drive from stunning beaches, crystal-clear ponds, scenic trails, and a short stroll to charming Wellfleet harbor and quaint town center. Relax and unwind at our brand-new Magnolia Spa (opening in June), featuring a hot tub and sauna. On-site massage therapy begins in July—ask us about exclusive guest rates!

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.

A walk in the park

A short walk & you’re in Nickerson State Park w/access to hike/bike trails & clean, secluded swim ponds. Kitchen: 4-burner cooktop, refrigerator, micro, coffee maker, & large toaster oven. Comfortable QUEEN bed, cozy living area w/TV (sports channels). Fast WiFi. Private full bathroom w/shower (also outside shower). Private outside entrance. Apartment is over 2-car garage - (NO cars are in garage - quiet is assured). No pets. No smoking. Main house is owner-occupied by a couple.

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.

Orleans, MA Luxury Getaway

Enjoy the best the Cape has to offer! Stay at this hidden gem in Orleans, MA. Easy access to Nauset Beach and Little Pleasant Bay. Large, luxurious, and family friendly with a big yard in a quiet neighborhood. Enjoy our gazebo, firepit, outdoor grill, outdoor patio dining, and outdoor shower. Inside, luxuriate in this 4 bed 4 bathroom with a modern kitchen, breakfast nook, dining room, and living room. Washer and dryer included in basement.

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

Nauset Nook

Relax and kick your feet up. Grill dinner on the private deck. Enjoy nature at your door (abutting wooded conservation land). Spacious and centrally-located. Only 2.5 mi. to Nauset Beach (ocean) and 3 mi. to Skaket Beach (bay). Five minute walk to town to enjoy great restaurants, coffee and ice cream shops, boutiques, access to Rail Trail (bike path), farmers market, Firebirds baseball games, galleries and more.