House holiday rentals in Orleans

4.87 out of 5 average rating, 211 reviews

Home in Brewster

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.

Top guest favourite

Home in East Orleans

5 out of 5 average rating, 18 reviews

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.

5 out of 5 average rating, 4 reviews

Lovely House 5 Min to Beach - Deck, Grill, Garage

Just 5 minutes from Cape Cod's stunning beaches like Rock Harbor and near Orleans' many shops & restaurants. This spacious home has a bright sunroom, AC, deck + grill, garage to park in, beach chairs & toys, dedicated workspace, and a fully equipped kitchen. Games & puzzles available for rainy days. Bike along the Cape Cod Rail Trail, with an entrance near our home, or go Hiking at a nearby trail. Ideal for families or groups, this home offers the perfect balance of relaxation and adventure.

4.94 out of 5 average rating, 17 reviews

Owl's Nest Cottage

Come stay at a charming, secluded 2-story cottage on the bay-side of historic Eastham, surrounded by woods and salt marshes. Decorated in a charming cottage-style, it features a wood burning fireplace, kitchenette, and wrap around porch. A close walk to Boat Meadow Beach, Rock Harbor and the rail-trail. Only a short drive to the Cape’s best beaches (First Encounter, Nauset, and Coast Guard), fresh-water kettle ponds, and Nickerson State Park. Just minutes to shops and restaurants in Orleans.

4.9 out of 5 average rating, 164 reviews

Home in Wellfleet

Wellfleet Woods Escape

Open kitchen + living + dining, w/ a wooden pitched ceiling and two sliders overlooking the deck, backyard +marsh. Functional kitchen with Farm sink, DW, cooking and pantry essentials. Two comfortable bedrooms with window AC's, new mattresses, and blackout curtains. Bathroom w/ tub/shower + plenty of towels for beach or house use. Outdoor shower is great in warmer months! Enjoy this quiet, tucked away Wellfleet spot with lots of walking trails and beautiful sunset views just down the road.

4.97 out of 5 average rating, 35 reviews

Home in Orleans

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!

4.97 out of 5 average rating, 179 reviews

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.

4.91 out of 5 average rating, 11 reviews

Home in East Orleans

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.

4.92 out of 5 average rating, 268 reviews

Home in Brewster

Privacy with Cape Cod charm

This lovely, private one bedroom apartment is located above the unused garage on the grounds of our classic half cape house, just a 3 minute walk to our private beach on the bay. It sleeps 2 with a double bed and has a full kitchen and bathroom, along with an outdoor shower, grill, fire pit and picnic table located in private yard. Linens will be provided. Coffee maker and coffee will be waiting for you...

4.96 out of 5 average rating, 26 reviews

Stunning Cape Cod Escape

Stunning 3-bedroom, 3-bathroom Cape Cod getaway with a lush, manicured backyard, multiple outdoor seating options, an outdoor shower and close to beaches, hiking trails, excellent restaurants and all the Cape has to offer. The home is fully stocked: Kitchen equipment, linens, towels, beach chairs, etc. so you have everything you need to have a memorable, relaxing, adventurous, joyous vacation.

Top guest favourite

Home in Orleans

4.9 out of 5 average rating, 58 reviews

Romantic Orleans waterfront cottage

ENHANCED CLEANING/DISINFECTING and SELF CHECK-IN ! The best of Cape Cod - literally on the edge of the gorgeous and picturesque saltwater town cove! This beautiful 1BR cottage is clean, comfortable and private, ... yet within a short walk to village center, shops, great eateries, attractions, etc. We just added propane fire pits and bluetooth speakers outside!!