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, 143 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, 120 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!

Top guest favorite

A two-story home with light blue siding and white trim is set amid lush greenery and flowering shrubs. A mailbox stands near the entrance, framed by well-maintained grass and colorful flower beds, enhancing the home's welcoming curb appeal.

Home in Barnstable

5 out of 5 average rating, 23 reviews

Osterville- New Renovation, Central AC, Beach Pass

Minimum age-28 years old. Osterville-Total renovation in 2022. Beach pass for all Barnstable beaches. Set on a gorgeous tree-lined street this 3 bdrm, 2.5 ba, office with futon, 2,900 sq ft with full A/C. Home has been updated to perfection. Brand new: kitchen with stone countertops, stainless steel appliances, bathrooms, hardwood floors, washer/dryer, queen-size sofabed, outdoor shower and deck. A mile to Dowses Beach, short walk to Joshua Pond, Osterville village & Armstrong Kelly Park

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, 235 reviews

WOW VIEW! Waterfront, Private 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!

Guest favorite

A charming cottage exterior is shown, featuring large, double-hung windows framed by blue shutters. Lush flower beds with pink, purple, and yellow blooms flank the front, providing a vibrant and inviting touch to the peaceful residential setting.

Cottage in Barnstable

4.88 out of 5 average rating, 111 reviews

Cozy Cottage - Steps to Craigville Beach

Come enjoy the beauty of Centerville, MA in our family's summer home! This clean and cozy duplex 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

Guest favorite

A bright living room features light blue walls and hardwood flooring, with natural light streaming through skylights. A cozy seating area includes a grey sectional and a light-colored side table, while a fireplace is adorned with decorative art. A television is positioned across from the seating arrangement.

Home in Barnstable

4.89 out of 5 average rating, 133 reviews

1-level fenced in yard Craigville Beach 2200sqft

Welcome to Midori On The Cape! This modern 4-bedroom, 2-bath, Cape-style house features ~2200 sq ft one-level Cape-style living in a quiet neighborhood, Free EV charging. 15000 sqft lot with fenced in flat grassy backyard, fire pit, swing set. Centrally located near Craigville Beach, Cape Cod Mall, vibrant Hyannis downtown and ferry terminal to Martha's Vineyard and Nantucket Island 1 living room, 2 dining areas, 4 super-sized bedrooms. Perfect for family staycation and gathering.

Guest favorite

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, 53 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 the hot tub stopped working and is no longer at the house - please disregard prior reviews that mention the hot tub!

Top guest favorite

The cottage exterior features a charming white facade with several windows illuminated in warm light. A welcoming front porch is adorned with potted plants, and an American flag is displayed. The surrounding lawn is well-maintained, enhancing the inviting atmosphere.

Cottage in Barnstable

4.99 out of 5 average rating, 156 reviews

Beach Glass Cottage - Pond Front

Come stay at the Beach Glass Cottage! A pristine pond front, completely renovated and tastefully decorated, 3 bedroom, 2 bathroom cottage in the heart of Hyannis. Truly the perfect get-a-way for family and friends. The Beach Glass Cottage is tucked away from the action, but within walking distance to Main Street Hyannis, which features eclectic shops, restaurants, bars, ice cream with mini golf and the Cape Cod Melody Tent is a short walk from the cottage as well.

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

4.89 out of 5 average rating, 65 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

4.87 out of 5 average rating, 138 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, 123 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!

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, 175 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!