Osterville, Barnstable vacation rentals

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Top-rated vacation rentals in Osterville, Barnstable

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Superhost

A charming carriage house with shingle siding is set against a blue sky adorned with fluffy clouds. A black Jeep is parked in front, showcasing the gravel driveway. Lush greenery surrounds the property, enhancing its inviting appearance.

Guesthouse in Centerville

5 out of 5 average rating, 137 reviews

Modern Fireplaced Carriage House with Beach Permit

Feel at home & relax in our new one bedroom carriage house. Modern yet classic Cape Cod style and elegance. Rest easy on a new Stearns & Foster king size mattress with designer linens and furnishings. Cozy up to the fireplace and flat screen TV. Custom bathroom, Bosch laundry units and small deck. Kitchenette with dishwasher drawer, under cabinet refrigeration, microwave, toaster, Keurig coffee maker, Starbucks coffee and various teas. We offer beach chairs, bags & towels for your convenience.

Superhost

Cottage in Barnstable

4.88 out of 5 average rating, 109 reviews

Cozy Cottage - Steps to Craigville Beach

Come enjoy the beauty of Centerville, MA in our family's summer home! This clean and cozy cottage is just a 5 minute stroll from the beach and provides guests with the perfect setting for a relaxing Cape Cod vacation. Perfect for couples, families, and small groups of friends, this cottage can comfortably sleep 2-5 guests and houses all the necessary amenities for your ideal vacation. Enjoy a cold drink on the back deck or soak up the rays at Craigville Beach - you have found your destination!

Superhost

A tree-lined street showcases a collection of charming shops and restaurants. Several cars are parked along the curb, with a clear blue sky above. The street is well-maintained, providing a welcoming view of Osterville Village's vibrant community.

Home in Barnstable

4.91 out of 5 average rating, 23 reviews

Peaceful Cottage in Heart of Osterville Village

Blossom Beach Cottage is a peaceful retreat centrally located within the heart of Osterville Village. Walking distance to Shopping, Restaurants, Ponds, Beaches, Parks, Biking Trails, and 1 mile to Dowses Beach. Our 2 Bedroom 1 Bathroom home features a large yard, BBQ, and fire pit to relax by with family and friends. Open-Concept living and kitchen. Gas wood stove. 1 Queen Bed, 2 Twin Beds , & 1 Queen Memory Foam Pull Out Couch. Marble walk-in shower, granite countertops, new furnishings!

Superhost

A spacious bedroom featuring a wooden bed frame and a large bed with neutral bedding. A colorful wall art piece adds visual interest above the bed. Natural light enters through two windows, and a full-length mirror is positioned nearby on one side.

Apartment in Falmouth

4.97 out of 5 average rating, 225 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

Superhost

A spacious deck features multiple black metal chairs arranged around tables. The beach house showcases a classic Cape Cod design with a large covered porch, glass doors, and a grill positioned to the side. Lush greenery surrounds the structure, under a partly cloudy sky.

Bungalow in Cotuit

4.98 out of 5 average rating, 58 reviews

Cozy Cape Cod Beach House Bungalow

Anyone who books this house will absolutely fall in love with it and the town of Cotuit! The beach house is on a private beach and is part of a larger family estate that has been in the family for four generations. The one-bedroom/two-bath rustic beach house is surrounded by nature. It provides enough space for solo travelers or couples looking for a romantic spot or a no-frills writer’s retreat. It's given our family such amazing memories and we're excited to share it with you!

Superhost

A light-filled living space showcases a comfortable striped sofa and a round coffee table. A dining area with a set of chairs is visible, positioned near a large window. The lofted sleeping area is accessed by a staircase, enhancing the open layout.

Guesthouse in Barnstable

4.9 out of 5 average rating, 60 reviews

Osterville Guest House

Charming 600 sq. ft. guesthouse located in the desirable village of Osterville. Take a short walk down Main Street for some shopping or dining. Along the way you may want to stop at Gone Chocolate for an ice cream or Dunkin Donuts for a quick coffee. You will have your choice of several restaurants to dine at including Five Bays Bistro, Crisp Flatbread Inc., Wimpy’s Seafood Market, or the newest restaurant in Osterville- the Chart Room at Crosby’s boat yard.

Superhost

Two lounge chairs are positioned around a low table, offering a clear view of Sam Pond. Lush greenery and trees frame the scene, providing a serene outdoor space. Lanterns are placed on the table, adding a subtle touch to the inviting patio.

Home in Barnstable

4.98 out of 5 average rating, 48 reviews

Sam Pond Oasis w/Grill, Patio, Beach Pass

Retreat to this beautifully remodeled, uniquely designed Osterville home located on Sam Pond. NOTE: Our home is currently NOT safe or suitable for children under the age of 6. Features include: * Expansive patio overlooking Sam Pond * Outdoor shower * Gas grill * Balcony * Pond views throughout the home * Barnstable beach pass provided Note: Unfortunately for the 2024 season the hot tub will not be available for guests. Sorry for the inconvenience!

Superhost

A cozy corner features a light brown armchair with a patterned pillow, coupled with a woven pouf. A small, black metal shelving unit holds decorative items and books. The wall is adorned with a star element, complementing the neutral tones of the space.

Guesthouse in Barnstable

4.87 out of 5 average rating, 127 reviews

Relaxing Cottage in Centerville Village

Welcome to my home! The cottage is located in Historic Centerville Village, it's a welcoming, bright and relaxing, studio space; perfect for a couple, or individual, to getaway on Cape Cod. Salt Tide Cottage is a private guesthouse with off-street parking and a serene outdoor space. It sits behind the main house with its own back yard space with fire pit. Just a short walk to the ocean, beaches, the library and the general store.

Superhost

An inviting bar area is presented with wooden walls and a high ceiling. Colorful nautical flags hang overhead, adding a maritime touch. A long wooden bar is lined with stools, and shelves display a variety of bottles. Large windows allow natural light to illuminate the space.

Apartment in Barnstable

4.95 out of 5 average rating, 122 reviews

Centerville Studio with Town Beach Pass

Apartment is centrally located on Cape Cod in Centerville and complies with all local, state and federal laws. Living room has 50" HDTV w/cable, couch & full kitchen. Bedroom has a queen bed with quality linens & towels & 27" TV w/cable. Also includes town beach pass for free parking, beach chairs, & towels, umbrella, cooler, propane grill on patio and washer & dryer too. Privacy fence and an abundance of beautiful plants!

Superhost

Home in Marstons Mills

5 out of 5 average rating, 165 reviews

Cape Cod Cotuit Cottage, 3 Bed Near Beaches

5 star rental Cottage in the beautiful village of Cotuit! This quaint 3-bedroom cottage is perfect for a getaway for friends and family. It is just a short distance to nearby beaches, local market, walking trails, Cape Cod league baseball stadium, shopping and restaurants. Relax on the private patio area and enjoy the peaceful, natural setting. Bring along your dog too!

Superhost

A serene porch area is framed by lush greenery, featuring white wicker furniture positioned thoughtfully on wooden decking. The entrance is enhanced by a covered awning, offering a shaded retreat surrounded by well-maintained garden plants, including hostas and flowering bushes.

Cottage in Barnstable

4.88 out of 5 average rating, 135 reviews

Osterville Charming Cottage in the Heart of Wianno

This Nantucket style cottage is tucked away down a private lane but right in the heart of Wianno, the most prestigious section of Osterville. Just a stroll to the Village and less than a mile from Dowses Beach make this seaside bungalow a perfect retreat. Occupancy tax of 14.45% applicable. Certificate Number: C0089770200

Superhost

Loft in Centerville

4.92 out of 5 average rating, 265 reviews

Cottage by the Sea ... Entire Loft

Cute cottage by the Sea.... Is located in the quaint mid-cape village of Centerville...Total separate out building... One mile to beautiful sandy beach.....Walk to Four seas ice cream...Walk to Centervillle candy store...Nantucket and Vineyard ferries 2 miles away.... Close to whale watching tours plus fun in the sun