Vacation rentals in Little Pleasant Bay

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.

7th Vacation in Harwich

Pleasant Lake Region of Harwich with deeded access to Long Pond and Cape Cod Rail Trail bike path. Newly renovated! Bright and Spacious! Sky-lighted modern kitchen, Master bedroom suite. Large deck with benches overlooking the backyard. Central heat & A/C. Hardwood floors. Game room with a foosball. A study area. Washer and dryer included. Outdoor shower. A fire pit and 5 car parking on a driveway on a corner lot make entertaining family and friends welcome! Let your Cape Cod adventure starts!

Antique Cottage with Path to Arey’s Pond

Relax at this unique and tranquil escape. Our small but charming one bedroom cottage offers a compact kitchen and a small full bath. A true antique from 1850, the unit is updated but remains quintessential Old Cape Cod. Private yard, outdoor shower, fire pit, laundry, and access to Arey’s Pond 350 yds down private path. A pet friendly getaway for a couple looking to relax in an ideal Orleans location. Close to Nauset Beach, Orleans, Chatham, shops & great dining. A super place to vacation.

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!

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.

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.

Shining Sea Condo

Ocean Edge Condo with cathedral ceilings! Beautiful private deck located on the 5th hole of the Ocean Edge golf course! Located within Eaton village. TWO KING beds, along with pullout couch allows 6 to sleep comfortably. Linens are included!! Large kitchen with washer/ dryer, AC units and heat throughout the entire unit. Wifi and THREE smart TVs with ROKU devices. Flexible dates allows guests to stay whatever length they would like instead of a mandatory week. Come enjoy!

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 Chatham Bars White Foam House Steps From Beach

Settle back in one of the rocking chairs on the front patio and take in the views of the harbor. Charm and warmth abound in this Cape Cod cottage with Chatham Seaside Links located across the street. Leave the car and walk to local restaurants and shops. Watch band concerts at the park and bask in the views from the Chatham Lighthouse. Go for a long stroll along Claflin Landing Beach all the way to the Fish Pier and buy the day's fresh catch.

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

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!

Secluded Cape Home | Fire Pit & Hammock

Escape to a secluded Cape Cod oasis we call the Hidden Hollow. This beautiful, family-friendly home features a cozy fire pit for relaxing evenings. Bring your furry friend along to enjoy the peaceful surroundings. Perfect for those seeking a tranquil getaway. Come enjoy stunning sunsets, sandy beaches, bike rides and a warm, welcoming atmosphere. Learn more below!