House holiday rentals in Orleans

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

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.

Private Bay Beach and Sunset Views! Dog friendly.

The beauty of Cape Cod awaits in this meticulous cottage with water views. Access to a private bayside beach is just steps away, across from the driveway and down a short sandy path. Beach chairs and beach towels included. Ride or walk 1 mi away to a great bike trail, or to National Seashore beaches, shops and restaurants. Or, relax at the cottage with updated amenities, appliances, comfortable beds, and a wonderful outdoor space with deck, fire pit, outdoor shower, lawn games and a hammock!

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.

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.

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.

Beautiful North Truro cottage with screen porch

This beautiful and restful four season cottage is a newly renovated barn over one hundred years old. It has two stories, fifteen by twenty feet, with a full bathroom and delightful screen porch surrounded by gardens. A sun filled retreat for 2 or 3 people.

Close to everything in Chatham

4 bedrooms ( 1 King bed, 3 Queen beds, 2 Twin beds and a Queen sofa sleeper), 2 1/2 baths, sleeps 10, 3 levels of living space, yard and patio, deck bbq, lounge chairs, large patio table with umbrella, outdoor shower and washer and dryer.

Studio cottage in Chatham Ma.

Comfortable studio cottage perfect for 1-2 people, queen bed, full bath with shower, kitchenette and outside shower when you come from the beach. Gas grill, brick patio with pergola and close to all that the cape has to offer.