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.

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.

Cape Escape Studio - Unit A

Studio Apartment with private entrance, king sized bed, full bath with shower. There is also a kitchenette with fridge, microwave, Keurig coffee maker and dinnerware. TV and Wifi are also included in the unit. Two Miles from Nauset or Skaket Beach The property is walking distance to downtown Orleans for shopping and restaurants. The Rail Trail Bike path is less than one mile away. This unit is attached to a private house with multiple units, please reach out to host with additional questions.

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!

Cape Cod Villa retreat, spa, venue, film location

Cape Cod Villa, an award-winning sanctuary on 1.8 acres of private conservation land, embodies refined luxury and serenity. Designed by Domapine Decor, this exclusive estate offers stunning interiors and panoramic pond views, placing guests moments from Cape Cod’s finest beaches, elite golf courses, and acclaimed dining. A haven of tailored indulgence, the villa offers private spa treatments and chef-curated dining, delivering an unparalleled escape in Lower Cape’s most sought-after setting.

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!

Apartment in East Orleans Historic Home

Walk to Town in 10 minutes or drive to Nauset Beach in 5 minutes! This newly renovated Home is centrally-located at the entrance to East Orleans. This Italianate historic home is within walking distance of many restaurants in Orleans, while offering easy access to the beaches. This home was built by Thomas A. Hopkins and the recent renovation has preserved much of the beautiful, interior architecture. It is a very peaceful location and parking access is conveniently onsite.

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.

Wequasset House - Quiet, spacious beach base

No cleaning fees! Keep it simple at this peaceful and centrally-located furnished home base for your Cape Cod adventures! Cozy 3-bed, 2-bath ranch house with deck. 3pm check in & 10am check out All rooms have end tables with built in charging. Bedrooms have window AC units & mini split in living room. Coffee station in kitchen with KCups refreshed in May New for 2026: 1. New larger living room couch 2. Couch in bunk bedroom 3. TV with Roku added to master bedroom

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.

Nauset Nook

Relax and kick your feet up. Enjoy nature from your own deck (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. Also, boat rentals/charters and golf nearby!