Vacation rentals with outdoor seating 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.

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for tidal flats. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

Charming Antique Cape Cod Cottage

Our cottage is situated in a lovely, landscaped yard with a private deck and back yard for our guests. We have a self check in that allows for privacy. While there is a feeling of privacy, you are close to stores and other conveniences. There are many walking trails nearby and beaches for outdoor activities. Perfect location for getting away or seeking adventure. Be sure to check out our fall and holiday specials. OCTOBER, NOVEMBER AND DECEMBER - BOOK 3 NIGHTS GET FOURTH NIGHT FREE!

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

Apartment suite|Firepit|Private Deck|Pond Access

Enjoy a stylish experience at this centrally-located spot. Our newly built apartment suite is within walking distance of Dennis Port for restaurants, yoga, and an organic market. Private parking, entrance, and deck along w/ water access to Swan Pond. A full kitchen & Bath equipped with a new LG washer + dryer makes this space feel like your home away from home. Explore, play, rest & relax. We have all you need for a wonderful retreat to make your trip to the Cape an enjoyable one.

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.

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

Steps to Private Beach in Chatham

2 Bedroom condo with views of the beach, ocean and marina. This wonderful condo is part of a beachfront/oceanfront complex, with steps to your own private beach in Chatham! We are within a mile of beautiful downtown Chatham and within a short walk to Chatham’s famous lighthouse beach and Monomoy Wildlife refuge. Whether by land or sea, there's something for everyone. This is a great place to make memories.

The Salt Pond Cottage

This is a free-standing private cottage that sleeps 2 comfortably. A spiral staircase leads up to a sleeping loft with a NEW QUEEN size Nectar bed! There is a full futon couch on the main level. The kitchen has everything you may need. The most spectacular thing about this home is its close proximity to the National Seashore. The salt pond, bike path, and freshwater ponds are also moments away!

Cozy Waterfront Apartment, Private Beach Access

Charming living space with nautical decor invites you to unwind off the grid for a few days. There is a window seat for reading, small high top for morning coffee, and all the accessories for a relaxing day at the beach. A five minute drive into town for local shopping and dining. Many scenic trails for walking and biking. Make us your base as you explore Cape Cod’s beautiful shores!