Vacation rentals in Osterville

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Top-rated vacation rentals in Osterville

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Top guest favorite

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, 145 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.

Top guest favorite

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

4.95 out of 5 average rating, 127 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/24. The reviews tell all!

Guest favorite

A vibrant green kayak glides over calm waters, with a person seated inside holding a paddle. In the background, a cottage displays large wall-to-wall windows reflecting the surrounding trees, providing a connection to nature.

Cottage in Sandwich

4.95 out of 5 average rating, 239 reviews

WOW LAKE VIEW! Waterfront, Prvt Beach, King Bed!

Wake up to magnificent panoramic views of a beautiful lake with waves lapping below your window! See a video tour on YouTube: "WOW View! Cape Cod Lakefront Cottage. Private Beach, King bed" Guests love the stylish, peaceful, open design; wall-to-wall, floor-to-ceiling windows; private beach with picnic table and chaise lounge chairs; a full, modern kitchen; luxurious King gel/coil bed, private office, bathroom's curved shower, AC, and much more! It's like being on your own luxury houseboat!

Top guest favorite

The exterior of a charming Cape Cod-style home is displayed, featuring a well-maintained lawn and symmetrical windows. The house is accented by subtle landscaping and a welcoming front porch with light fixtures. American flags are placed by the entrance, enhancing its inviting appearance.

Home in Barnstable

5 out of 5 average rating, 26 reviews

Newly Renovated Cape, walk to Osterville

Welcome to Pond Street and your cape cod summer vacation. This fully renovated single family home is situated in the heart of Osterville on a large half acre lot. The home features an open floor plan with all new finishes inside, central AC and a newly landscaped outdoor entertaining area and putting green! This is a kid-friendly home complete with necessities for infants and children. Just a short walk to downtown Osterville offering the area's best beaches, dining, shops, and much more!

Top guest favorite

The beach house is set against a backdrop of lush greenery, featuring a wraparound porch with white railings. Light-colored siding and windows create a bright appearance, while a sandy path leads up to the entrance. A seated area and natural landscaping enhance the outdoor surroundings.

Bungalow in Cotuit

4.98 out of 5 average rating, 59 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!

Guest favorite

A bright living area features a striped couch adorned with a 'SUMMER HOUSE' pillow, complemented by a cozy armchair. Natural light enters through windows with white blinds, and wooden beams add a touch of character. A decorative coffee table sits in the center, enhancing the inviting space.

Guesthouse in Barnstable

4.9 out of 5 average rating, 69 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.

Guest favorite

The exterior of Salt Tide Cottage is shown, featuring a white-sided structure with a dark blue door and a large star decoration. A small seating area with two chairs and a table is positioned in front, surrounded by well-maintained green grass and trees.

Guesthouse in Barnstable

4.88 out of 5 average rating, 145 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 hammock. Just a short walk to the ocean, beaches, the library and the general store.

Guest favorite

The inviting front of a blue house features a warm entry door flanked by two outdoor light fixtures. A stone pathway leads to the door, bordered by vibrant flowerbeds filled with sunflowers, daisies, and other colorful blooms, enhancing the home's welcoming appearance.

Apartment in Barnstable

4.95 out of 5 average rating, 125 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!

Guest favorite

A historic lighthouse stands beside a renovated white keepers home, both set on a lush green lawn. The Atlantic Ocean stretches out in the background under clear blue skies, offering a serene coastal view.

Lighthouse in Pocasset

4.94 out of 5 average rating, 113 reviews

Wings Neck Lighthouse

Once in a lifetime experience to stay in a Lighthouse. Historic, unique and charming but with all of the conveniences that make a great vacation. Just feet from the Atlantic with 360 degrees of ocean view. Beautiful, peaceful and memorable all year long. Sandy private association beach just steps away. Expansive lawn and patio for enjoying salt air, waves, boats and sunsets.

Top guest favorite

An outdoor patio area is illuminated softly at dusk, featuring a dining set with a table and several chairs arranged on a patterned rug. Lush greenery and flowering plants surround the space, while lanterns provide a gentle glow, enhancing the tranquil environment.

Home in Mashpee Neck

5 out of 5 average rating, 187 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!

Top guest favorite

A cozy studio space is highlighted by sloped ceilings and wooden flooring. A bed is positioned beside a window, complemented by a small television and a seating area. A dining table with chairs occupies one corner, enhancing the room's functionality.

Guest suite in Marstons Mills

4.97 out of 5 average rating, 164 reviews

Dog friendly, 2.4 ml bch, 1 bedrm, stdio priv entr

Sunny, clean 2 rm studio + w/door separating sleep areas Priv fenced in yard 5 to 10 min bches ponds 10-15 min to Lrg bches Separate entrance 3 beds: 1 queen 2 tw kitchenette w/micro, sm frig toaster, toaster oven, hot plate personal grill, small deck, fenced in yard w/swing set. Your dogs will be completely separate from my 2 little dogs. Yards are private.

Superhost

A charming Nantucket style cottage is surrounded by lush greenery, featuring a well-maintained garden with flowering bushes. The exterior showcases a light-colored facade, white trim, and a blue door. A stone pathway leads to the entrance, enhancing the inviting garden setting.

Cottage in Barnstable

4.88 out of 5 average rating, 142 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