Vacation rentals in Little Pleasant Bay

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Top-rated vacation rentals in Little Pleasant Bay

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Top guest favorite

An outdoor seating area features two wicker chairs with soft grey cushions positioned around a circular fire pit. The fire pit is surrounded by gravel, creating a designated space for relaxation among mature shrubs and greenery.

Tiny home in Brewster

4.98 out of 5 average rating, 52 reviews

Whitecap Cottage-Tiny Luxury! PETok-Fireplace/pit

Whitecap Cottage 🤍 🌊 -located within The Salty Doors cottage community! 🌟Fully renovated 🌟Fully equipped kitchen 🌟Washer/Dryer combo 🌟High quality memory foam Queen mattress 🌟Cotton linens 🌟Down pillows/blankets 🌟Cotton towels 🌟 Shower toiletries 🌟Custom dining nook for 2 🌟Private screened in porch 🌟Private patio-propane fire pit/seating 🌟BBQ propane grill 🌟Two 43” smart TVs 🌟Stand up shower/full BR 🌟1 pet allowed 30lbs and under *additonal $30/per night pet fee will be due after booking

Guest favorite

Home in Orleans

4.95 out of 5 average rating, 21 reviews

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.

Top guest favorite

A clean bathroom is equipped with a modern white toilet and a sleek vanity. Decorative framed shell prints adorn the wall above, while a countertop holds various bottles and a hand soap dispenser. Natural light streams in, adding a bright touch to the neutral tones.

Guest suite in Chatham

4.99 out of 5 average rating, 241 reviews

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table just steps to a fresh water pond & outdoor shower. The friendly, cottage-style decor is inviting w/queen-size bed, couch, ample closets, private bathroom w/shower, small dining area w/microwave & fridge (no stove, no bbq); writing table, WiFi, Roku & DVD player. Enjoy the water view! Minutes by car to downtown Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

Top guest favorite

An inviting entryway is showcased, featuring a warmly decorated door and charming wooden accents. A blue chair sits beside a small table, complemented by a vibrant area rug. Surrounding plants add a touch of greenery, enhancing the welcoming atmosphere of the tiny house retreat.

Place to stay in Wellfleet

4.97 out of 5 average rating, 239 reviews

Romantic Cape Cod Tiny House + Hot Tub

Welcome to the Romantic Hideaway, our magical, secluded tiny house nestled between lush gardens and the woods alongside our property. Just a short drive to ocean beaches and freshwater ponds, and a pleasant walk to the quaint center of Wellfleet. Wake to birdsong and enjoy fresh muffins on your sunny, private deck. Your stay includes access to our Magnolia Spa with hot tub and sauna (June+); massage is available in July at special guest rates. A sweet, quiet escape on the Outer Cape.

Guest favorite

A light blue wall features a large wooden map of the world, highlighting various countries. An illuminated dining area is furnished with a round table and wooden chairs. Above the kitchen area, a model sailboat is suspended, enhancing the coastal theme.

Condo in Brewster

4.88 out of 5 average rating, 258 reviews

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. One king bed and one queen, along with pullout couch allows 6 to sleep comfortably. Linens are included!! Large kitchen with washer/ dryer, AC in living room and heat throughout the unit. Wifi and two smart TVs with ROKU devices. Flexible dates allows guests to stay whatever length they would like instead of a mandatory week. Come enjoy!

Guest favorite

A covered outdoor seating area features comfortable sectional sofas and a central coffee table with decorative elements. Soft fabric drapes frame the space, and a hot tub is positioned nearby, with views of the surrounding nature visible in the background.

Cottage in Eastham

4.95 out of 5 average rating, 241 reviews

The Breeze Overlooking Minister's Pond

The Breeze is a luxurious, romantic cottage by a serene freshwater pond, surrounded by vibrant gardens. Perfect for a peaceful getaway, enjoy kayaking, canoeing, and relaxing on the dock, or explore nearby trails and the Cape Cod Rail Trail with provided bikes. Unwind with evenings by the fire pit, refreshing outdoor showers, and a plush queen bed for ultimate comfort. This private oasis offers tranquility, natural beauty, and 5-star attention to detail for your perfect escape.

Guest favorite

The image captures a sandy beach with gentle waves rolling onto the shore. The ocean is visible extending to the horizon, displaying a gradient of deep blue and green hues under a clear sky with wispy clouds.

Apartment in Harwich

4.9 out of 5 average rating, 283 reviews

The Secret Garden

Bright and spacious garden level apartment. One floor living, one queen bedroom, private bath, living room with queen pullout and limited kitchenette. Tranquil setting. Your own entrance and patio. A mile to Pleasant Bay, Eastward Ho and Wequassett Inn, shopping, restaurants and beach. Walk the labyrinth, gardens and fairy gardens. Take an outdoor shower. Cable TV in bedroom as well as living room plus wifi. The hosts live on the top floor of the home. Off season discounts.

Guest favorite

An elegant soaking tub is presented with scattered rose petals floating on the water's surface. A wooden bathtub tray holds toiletries, a decorative book, and a glass, enhancing the serene atmosphere. A plush bath mat featuring the word 'BEACH' is situated nearby.

Apartment in Brewster

4.96 out of 5 average rating, 162 reviews

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.

Top guest favorite

Vacation home in Chatham

5 out of 5 average rating, 48 reviews

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, the beach, a movie theater, Veterans Field for summer Chatham A’s games, The Squire, & more! This cozy, modern, & newly renovated apartment is ideal for a couple or two friends with an open living room & kitchen space + private patio. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

Guest favorite

A landscaped outdoor area features a winding pathway lined with smooth stones and dotted with small, low-lying lights. Lush greenery surrounds the path, providing a natural backdrop, while patches of grass and decorative gravel create a serene and inviting atmosphere.

Guest suite in Orleans

4.93 out of 5 average rating, 89 reviews

Spacious Guest Suite Close to Town

Our second floor guest suite is on a quiet street, within walking distance to the center of town and a quick drive to ocean and bay beaches. Featuring an open floor plan and high ceilings, the suite includes a living/dining room, kitchenette, reading nook, private bath, and spacious bedroom. Guests have their own outside entrance and tiny deck. Our family of four (+dog & cat) live downstairs. We are happy to provide tips and recommendations, or let you enjoy your privacy.

Guest favorite

A wooden sign reading 'Snowtop Guests' is displayed among greenery, with soft lighting enhancing its visibility. The sign is positioned near a stone pathway leading to a grassy area, inviting guests to approach the entrance. Lush plants surround the scene, providing a natural ambiance.

Guest suite in Orleans

4.92 out of 5 average rating, 184 reviews

Charming Old Cape Cod

Relax and enjoy spending time at Snowtop on the Town Cove, many activities including sailing, paddle boarding, water skiing and spectacular sunsets! A short walk to swim, sit on the sand or take a beach walk. The offered space has a private entrance with bath, bedroom with a king size bed, a sunny living room with dining table over looking the water where you could choose to dine in, have coffee in the morning or play a game.

Guest favorite

The kitchenette is equipped with essential appliances like a microwave and coffee maker, situated on a wooden surface. Light streams in through the glass door leading to the private deck, while shelves store various condiments and cups. A cozy rug lies at the entrance.

Guest suite in Harwich

4.91 out of 5 average rating, 45 reviews

BB's Hideaway (A Cape Cod Experience)

(NO SMOKING) Guest Suite, Q-Bed, , with adjoining / kitchenette , coffee/tea bar, microwave, small fridge. Steps out onto a private enclosed porch and newly added private deck with gas grill . A true Cape Cod experience featuring a private covered outdoor shower. This little gem is located in a serene setting that is a short drive from some of the best Cape Cod beaches, fresh water ponds, bike trails and shopping.