Holiday rentals in Orleans

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 overlooking picturesque Town Cove. The view in the photo is your front yard. Guests often enjoy sitting outside to watch boats drift by and the sky change color to a sunset. Nestled on a quiet road, Snowtop is 3 miles from beautiful Nauset Beach and 2 miles from the center of Orleans.

Antique Cottage with Path to Arey’s Pond

Relax at this unique and tranquil escape. Our small but charming one bedroom cottage offers a compact kitchen and a small full bath. A true antique from 1850, the unit is updated but remains quintessential Old Cape Cod. Private yard, outdoor shower, fire pit, laundry, and access to Arey’s Pond 350 yds down private path. A pet friendly getaway for a couple looking to relax in an ideal Orleans location. Close to Nauset Beach, Orleans, Chatham, shops & great dining. A super place to vacation.

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.

10 min walk to Beach - Amazing View & Huge Deck

Enjoy an incredible view of Duck Meadow Tidal Marsh from this cozy cottage. Only a 10 minute walk to Boat Meadow Landing, a great bayside beach. Sip your morning coffee on our huge deck while enjoying the view. The deck includes a retractable roof if you would prefer to sit in the shade. Only minutes from incredible restaurants & shops in Orleans. This home includes AC, office space w/ monitors & a natural gas fireplace. Near the Cape Cod Rail Trail, hiking trails and numerous beach options!

Orleans Pleasant Bay CulDeSac 4BR 2BA

Welcome to Orleans, Cape Cod, where the raw beauty of the Atlantic meets the quiet charm of Cape Cod Bay. Nestled between Eastham and Chatham, Orleans blends New England charm with unforgettable natural landscapes. Our home's cul-de-sac location near Pleasant Bay is a short drive to Nauset and Skaket beaches the best of the Cape! A FREE private salt water beach with great swimming within a short bike ride away. Expansive deck, large outdoor eating area for evening get-togethers and BBQ's.

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 an outdoor shower. Master BR has Queen bed. Second BR has a queen bed with a twin pull out. We have tiny ants in the kitchen. We set ant traps and a mint plant by the sink.

Nauset Nook

Ten minute walk to town! Foodie’s heaven. BOTH Ocean and Bay beaches! Only 2.5 mi. to Nauset Beach and 3 mi. to Skaket Beach! Great apartment with attention to detail. Apartment completely renovated in 2024 with two mini splits for easy, effective cooling and heating. Enjoy fantastic restaurants, coffee and ice cream shops, boutiques, access to bike path, farmers market, Firebirds baseball games, galleries and more. Abutting wooded conservation land - private yard. Perfect cozy getaway :)

Petite Antique, location, location, location

This cozy cottage is an ideal base for exploring the Cape + Islands. 15 min. walk to Dyer Prence Beach /Eastham side of Rock Harbor. Also close by is the wild Atlantic Ocean, fresh water ponds, and Bike Trail. Close to Orleans center, enjoy restaurants + shopping. Nearby towns with unique attractions, Chatham, Provincetown + Hyannis for ferries to Nantucket +Martha’s Vineyard, must do day trips! The property owners and their dog Charlie girl live in the barn at the rear of the property.

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

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

August Avail + 1 mi. to Skaket Beach + Game Room

Escape to this charming cabin just 1 mile from Skaket Beach! Perfect for families and groups, the home sleeps 8 with 3 bedrooms featuring 2 queen beds, 2 twins, and a twin bunk bed. Enjoy two separate living areas, central AC, a fun game room, and an outdoor patio and a playground for the kids. After a day at the beach, relax in comfort with plenty of space to gather. Ample parking accommodates 4–5 vehicles and an outdoor shower.