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

A charming cottage exterior is surrounded by lush green grass and vibrant flower boxes. The house features a shingle facade and windows adorned with traditional shutters. A tranquil garden area adds to the serene atmosphere, inviting guests to enjoy the peaceful surroundings.

Cottage in Orleans

4.99 out of 5 average rating, 97 reviews

Hobbit Cottage with Marsh View

Are you special enough to stay at the Hobbit Cottage? All of our tenants have been magical so far and we want to continue that trend! This cute little house is on a lovely marsh where you will hear birdsong while you enjoy the ever changing view of the gentle wetland. A mini paradise nestled in a quiet neighborhood, it is an easy bike ride or a short drive to Nauset Beach. Tiny and cozy, the cottage has every amenity for a comfortable stay! (7 Day SATURDAY - SATURDAY Minimum in July and August.)

Guest favorite

The private yard features a fire pit surrounded by blue chairs, with a small patio table and umbrella nearby. Lush greenery and flowering plants line the path, leading to the entrance of the cottage, while a wooden fence provides a sense of seclusion.

Home in Orleans

4.96 out of 5 average rating, 25 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

An aerial view captures a cottage nestled among vibrant green trees, showcasing the surrounding natural landscape. A glimpse of the ocean is visible in the distance. The cottage features a deck facing the woods, providing a serene and secluded ambiance.

Home in Orleans

5 out of 5 average rating, 27 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.

Top guest favorite

A spacious backyard features a well-maintained lawn, surrounded by lush greenery. A wooden deck with seating overlooks the area, complemented by colorful flower pots. A hammock is nestled between trees, inviting relaxation. Comfortable chairs are arranged for outdoor enjoyment.

Guest suite in Harwich

4.99 out of 5 average rating, 620 reviews

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.

Top guest favorite

A serene dock extends over calm waters, featuring two Adirondack chairs positioned beside vibrant potted flowers. Lush greenery frames the scene, providing a peaceful backdrop for relaxation. The setting invites guests to unwind and enjoy the tranquility of the freshwater pond.

Cottage in Eastham

4.95 out of 5 average rating, 255 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.

Top guest favorite

A private balcony features a small white table and two wine glasses, set among comfortable lounge chairs. Lush greenery surrounds the area, creating a serene and secluded outdoor space, perfect for relaxation.

Guest suite in Eastham

4.96 out of 5 average rating, 138 reviews

Cape Cod Heaven

Private one bedroom with full bath and balcony overlooking garden and a peek at the bay. Great location less than a mile from beautiful First Encounter Beach, a wonderful bay beach, and five minute walk to freshwater pond with sandy beach. Ocean beaches and bike trail close by. Bring your bikes or kayaks, or rent them, and enjoy all the Cape has to offer. Great for singles, couples, small families. Has a small refrigerator, microwave and Keurig. There is not a kitchen.

Top guest favorite

The inviting living area features large windows with blue curtains, allowing natural light to brighten the space. A comfortable sectional sofa is situated around a small coffee table. A door leads to a private balcony, while a bar counter with stools is visible in the background.

Condo in Chatham

4.97 out of 5 average rating, 356 reviews

In town Pied-a-Terre. Urban oasis.

Bright, Sunny, great in-town location. CLEAN, SAFE & PRIVATE and spacious, hidden ABOVE shops, behind the Main Post Office. Great for Romantic Getaway, WEDDING GUESTS, business trips, overflow guests or just a quick get-away break. Comfortably furnished, thoughtfully outfitted. Full Kitchen, Quality linens, duvet etc. Walk to everything. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

Superhost

An open living area features a comfortable gray sofa facing a round dining table and chairs. A full kitchen is equipped with modern appliances, including a stainless steel refrigerator. Natural light brightens the space through large windows, complemented by light-colored wooden flooring.

Cottage in Dennis

4.86 out of 5 average rating, 550 reviews

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

Guest favorite

The cottage is set amidst lush gardens, featuring a wooden archway adorned with hanging planters and red flowers. A stone pathway leads up to the charming entrance, surrounded by vibrant greenery and trees under a clear blue sky.

Cottage in Eastham

4.99 out of 5 average rating, 224 reviews

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!

Top guest favorite

A sandy path meanders through tall grass, leading toward a tranquil sunset in the background. The sun casts a warm glow over the horizon, suggesting the evening calm of the beach area. Soft greens and earthy tones create a peaceful natural setting.

Apartment in East Orleans

4.95 out of 5 average rating, 311 reviews

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!

Superhost

A brightly colored blue door welcomes guests, adorned with a seasonal wreath. Inside, a warmly lit entryway reveals a small table with a lamp, providing a cozy introduction to the space. The living area is visible through an adjacent doorway.

Guest suite in Orleans

4.89 out of 5 average rating, 208 reviews

Charming Old Cape Cod

Escape to Cape Cod this fall and winter for a peaceful, scenic getaway. Enjoy crisps rounds of golf, take a bike ride on the Rail Trail, stroll serene beaches, explore charming fairs and holiday events, or watch birds and boats from the windows of Snowtop on Town Cove. Discover the magic of Cape Cod-where cozy meets coastal, and every season has its special charm!

Guest favorite

A serene beach landscape stretches under a clear blue sky, with soft sandy shores meeting calm waters. A small sailboat rests on the sand, surrounded by lush green shrubs and trees in the distance, enhancing the natural beauty of the coastal environment.

Apartment in South Orleans

4.93 out of 5 average rating, 140 reviews

Walk to private beach, spacious peaceful apartment

2026 RESERVATIONS CALENDAR WILL OPEN SEPT 1. Fully separate, pristine 1-BR apartment a short walk from Little Pleasant Bay, in our secluded home on wooded lane, looking out on a small pond. Private entrance and stairs to airy, light-filled, tastefully furnished rooms, with full kitchen and private laundry room. Near Orleans and Chatham.