Family-friendly vacation 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.

Steps to Rock Harbor | AC, Deck, Outdoor Shower

Welcome to Rock Harbor! Just steps from one of Orleans’ most loved harbor areas, this newly renovated Cape Cod cottage blends classic coastal charm with modern comfort. Whether you're heading to the beach, catching a sunset at Rock Harbor, exploring the National Seashore, or day-trip to Provincetown, Chatham, or Hyannis, this is an easy & relaxing place to come home to. Perfect for families, couples, or friends, the cottage sleeps up to 6 & has been thoughtfully designed for a comfortable stay.

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.

Large Sunny Deck, Harbor View, Walk to Town.

Classic little Cape cottage in an ideal location. Less than ten minute drive to amazing ponds and bayside or ocean beaches. Views of the harbor from the large sunny deck with attached outdoor shower. Ten minute walk into town along Duck Creek marsh & over scenic Uncle Tim’s Bridge. Visit the shops & galleries, have lunch or grab a drink at one of the many restaurants in town. Walk to the fish market and come home grill dinner on the deck. 15 minutes bike ride to the closest ocean beach.

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

Welcome to SEAGLASS COTTAGE! 🔸 200 MBPS WIFI 🔸 Steps to sandy beach on a crystal clear pond 🔸 Pet friendly 🔸 Linens & towels are included. Beds will be made 🔸 Swim, fish or use our 2 kayaks & 2 SUP’s 🔸 Bluestone private patio w/waterviews+charcoal BBQ 🔸 Outdoor shower 🔸 Sunroom w waterview 🔸 Washer+dryer 🔸 Fully equipped kitchen w/Carrera marble counter 🔸Gas firepit 🔸Ductless A/C & Heat 🔸Small library of books, didn't finish the book? Take it! 🔸Pet fee $25/day

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!

Cottage Getaway walk to beach

This Cute As Can Be Beach House is looking for guests! Just a five minute stroll to the beach, The Cottage is the perfect spot for a getaway. Open floor plan with spacious living-room, two bedrooms and bath. Large yard with outdoor shower and a hammock big enough for two! Includes beach chairs, towels, cooler. A true gem! Amenities -Air Conditioning -Heat -Smart TV -Wi-Fi -Gas grill/firepit -Two patios -Washer/Dryer -Outdoor shower - Parking -Adirondack chairs -Amazing sunsets

Spacious Guest Suite Close to Town

Our second floor guest suite is on a quiet street, within walking distance to the center of town and a quick drive to ocean and bay beaches. Featuring an open floor plan and high ceilings, the suite includes a living/dining room, kitchenette, reading nook, private bath, and spacious bedroom. Guests have their own outside entrance and tiny deck. Our family of four (+dog & cat) live downstairs. We are happy to provide tips and recommendations, or let you enjoy your privacy.

Distiller’s Cottage Nauset Beach East Orleans, MA

Escape to this 1 bedroom cottage on a private country compound 1.5 miles from Nauset Beach, 1.5 miles from downtown Orleans. This 750 sq ft two-story cottage provides all the amenities necessary for a couple or small family (2 adults with 2 children - 2 adults max, 4 w/ children as it is a 1 BR with no privacy barrier) including linens. ONE parking space max. Bathroom is located on first floor. No pets or 3rd party bookings. Chickens free range on property.

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