Holiday rentals in Pleasant Bay

Beautifully renovated home, outdoor space, pets ok

Sea~a~Bella - Your perfect Chatham family vacation is here. You will find three beautiful, scenic beaches within walking distance providing the perfect summer Chatham day. Minutes away from restaurants, shopping and Cape Cod Baseball, there is something for everyone in the family. This modern home with plenty of space will ensure a wonderful stay. The backyard has plenty of room for games in addition to a new Outdoor kitchen and natural gas fire pit to relax comfortably on those cooler nights.

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.

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.

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.

NEW Luxury Waterfront - Hot Tub, Deck & Waterviews

Welcome to Aunt Laura’s Retreat, a newly renovated waterfront home ideal for families and groups seeking a relaxing Cape Cod getaway. Enjoy beautiful water views from every room, direct access to Swan Pond for kayaking and beautiful sunsets to end the day. Unwind in the hot tub, dine on the deck overlooking the water, or relax on the lower patio with a grill and cozy seating. - Direct access to Swan Pond - 5 min drive to Sea Street Beach - Close to Cape Cod Rail Trail & dining

Sophisticated, Private Cape Cod living

LOCATION: 3/4 mile off main road (unpaved road). Located on the town line of Brewster and Orleans with less than 5 minutes to Chatham or Harwich by car. Nauset and Skaket beaches are less than 3 miles away. Nickerson state park less than 1 mile away. Cape Cod National seashore is located within 7.2 miles of our property. Shopping on Main Street in Chatham is 15 minutes. Enjoy a nice, tranquil walk, listen to the birds or feast your eyes on the surrounding conservation land.

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

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.

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

The Hideaway - Harwich Port Getaway

Your family will be close to everything Harwich Port has to offer when you stay at this centrally-locally oasis! Central Air! TV in everyroom! Large fully fenced in backyard for summer cookouts & fires! Come stay in our newly renovated home that has everything you will need. Only minutes from major beaches, shopping, restaurants and all of the beautiful things Cape Cod has to offer. *more outdoor photos to come soon!

Walk to Lake + Fire Pit | Near Nauset + Sleeps 10

Let the Cape Cod breeze clear your thoughts and the sound of birdsong reset your pace. This beautifully renovated Orleans retreat sits on a quiet wooded lot — walk 5 minutes to Pilgrim Lake, stroll through the woods to Arey's Pond, or drive 7 minutes to Nauset Beach. Three bedrooms sleep up to 10, with a designer coffee bar, firepit, grill station, and game room waiting for you.