Vacation rentals in Pleasant Bay

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Top-rated vacation rentals in Pleasant Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

Apartment in Oak Bluffs

4.92 out of 5 average rating, 109 reviews

Absolute Best Location on the Island

Ideal location for visitors in the middle of the most lively, diverse, fun town on Martha's Vineyard. This property is certified by the United States Department of Interior as a National Historic Property. The ferry terminal, restaurants, shops, markets, harbor, historic sites, entertainment, public transportation, and a clean sandy beach are all within minutes. A vehicle is not necessary. IF UNAVAILABLE: SIMILAR WALKABLE SISTER PROPERTY in Vineyard Haven: https://www.airbnb.com/rooms/49016488?

Guest favorite

Home in Barnstable

4.87 out of 5 average rating, 155 reviews

Cottage with private beach in Hyannis Port

Make your Cape Cod trip unforgettable in this Exclusive Harbor Village Cottage located right in Hyannis! Enjoy this recently updated 2-bed, 2-bath vacation home with access to private beach, beautiful outdoor deck, and peaceful ocean views. Follow the beach path 900 feet to the beach! Only minutes from downtown Main Street, the Melody Tent and Hyannis harbor. Whether you spend your days exploring the Cape, sunbathing on the beach, or relaxing on the deck, you will be sure to love this house!!!

Superhost

Condo in Provincetown

5 out of 5 average rating, 5 reviews

Spacious Ptown Escape | Patio, AC, 2-Car Parking

We've been renting this for years, and our previous listing had 125 reviews and a 4.98 star rating! Experience modern coastal charm at our stylishly designed 2-bedroom vacation rental, ideally situated just a short stroll from the stunning beaches and vibrant attractions of Provincetown. With thoughtful decor, a prime location, parking for 2 vehicles, and a welcoming atmosphere, this getaway is the perfect way to experience Provincetown like a local and for creating unforgettable memories.

Superhost

Home in Yarmouth

4.88 out of 5 average rating, 153 reviews

* Walk to the beach - Swiss Beach House! *

Walk to the beach! Less than a 1/2 mile (0.7 km)! Perfect spot for paddle boarding. Paddleboards and gas grill (available in summer). Private European - style house. Rustic charm. Laid-back atmosphere. 3 Bedroom, 2.5 bathroom. Comfortably sleeps 6-7, up to 8. Fire pit. Outdoor shower. Farm table for group dining. Fantastic central Cape Cod location. Natural environment. 15 min. to Hyannis for ferries to Nantucket or Martha's Vineyard. Enjoy something unique. Experience the real Cape Cod.

Top guest favorite

Home in Sandwich

5 out of 5 average rating, 32 reviews

Cape Cottage - Kid Friendly * Firepit * PetsOK

The Cape Cottage is a private, tranquil Cape Cod-style cottage nestled near historic downtown Sandwich and just 6 minutes from the ocean. Newly renovated, this home is tastefully designed with a blend of coastal, farmhouse and antique design elements. We thoughtfully curated the home's details to evoke the comforts of home and give it unique charm that pays homage to quintessential New England and Cape Cod's scenic beauty. Check out our IG @thecapecodcottage for more pictures and vibes.

Superhost

Cottage in Brewster

4.85 out of 5 average rating, 62 reviews

BeachFront Private Beach Amazing Views WIFI

Sunset Cottage, Amazing Location on a secluded bluff, with fantastic views of Cape Cod bay, Beach front! A/C WIFI Simple Cottage, natural setting, safe quiet clean Beautiful huge Private beach for 3 cottages and the main house. All photos are on the property Desirable Brewster MA on the Bay. Amazing sunset views over the ocean from every room. Full kitchen, large living room, Master Queen bedroom, 2nd queen bedroom (coolgel matress), Long wide private beach. 360 feet long!!

Guest favorite

Cottage in Provincetown

4.81 out of 5 average rating, 474 reviews

Private cottage green friendly and pet friendly

. Private quiet Restored and renovated stand alone cottage in the west end location complete with new renovation of kitchen and bathroom. Recently added an Extended bay window, new skylight, and brand new dishwasher Green friendly and pet friendly From June 28 to September 10 this is only a Saturday to Saturday rental only . Bear week and carnival week is a surcharge of $50 more per night. When you bring a pet there is a separate cleaning fee of $40 non refundable

Guest favorite

Home in Plymouth

4.93 out of 5 average rating, 41 reviews

The Lake House Paradise!

Escape to our serene lake house with breathtaking views & endless opportunities for outdoor adventure. With a dedicated workspace, stay connected while enjoying tranquility. Take a paddle on the lake with kayaks & pedal boat, or relax on the patio with outdoor fire pit. Fully furnished & decorated, feel at home cooking in the fully equipped kitchen or curling up in the cozy living room. Book your stay today and experience the magic of nature firsthand!

Top guest favorite

Guesthouse in Provincetown

5 out of 5 average rating, 68 reviews

Historic Cottage Ideal Location, Stylish Charm

Beautifully renovated cottage in incredibly central Provincetown location! Less than a block to The Boatslip and the beach! Open studio cottage has stunning tile throughout, kitchenette, excellent air conditioning, ceiling fan, living area with couch, breakfast bar/desk, farmhouse sink, 1 queen bed, outdoor seating area, shared backyard (with seating, grill, and outdoor shower), and reliable high-speed wifi. Fresh, whimsical styling & worldly charm.

Superhost

Home in Edgartown

4.91 out of 5 average rating, 54 reviews

Updated Beautiful Cottage in Edgartown AC

A true island charmer. Light, airy and central-air-conditioned home offers all the comforts of modern living centrally located in Edgartown. Recently completed extensive upgrades completed enhance all of the space, including a new kitchen, both bathrooms, basement, and more. A spacious outdoor furnished deck with enclosed outdoor shower and an expansive grassy lawn make for a great space to relax. Great location makes Island travel a breeze.

Superhost

Home in Orleans

4.89 out of 5 average rating, 57 reviews

Romantic Orleans waterfront cottage

ENHANCED CLEANING/DISINFECTING and SELF CHECK-IN ! The best of Cape Cod - literally on the edge of the gorgeous and picturesque saltwater town cove! This beautiful 1BR cottage is clean, comfortable and private, ... yet within a short walk to village center, shops, great eateries, attractions, etc. We just added propane fire pits and bluetooth speakers outside!!

Top guest favorite

Home in Yarmouth

5 out of 5 average rating, 24 reviews

Cape Cod Retreat

Recently updated Cape Cod vacation home close to everything in the heart of South Yarmouth beach neighborhood. Nantucket Sound and Bass river beaches just a short walk away. Close to Forest Rd bike path leading to the CC Rail Trail. Top Cape restaurants and many amenities just a few blocks away.