Holiday rentals in Osterville, Barnstable

Guest house 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.

4.95 out of 5 average rating, 229 reviews

Cottage in Sandwich

WOW VIEW! Waterfront w/ Private Beach, King Bed!

Wake up to magnificent panoramic views of a beautiful lake with waves lapping below your window! Search on YouTube for tour: "WOW View! Cape Cod Lakefront Cottage. Private Beach, King bed" Guests love this stylish and open cottage on the shore of a large recreation lake with its own private beach. Wall-to-wall floor-to-ceiling windows with a new modern kitchen, luxurious King gel/coil bed, office space, bathroom with curved shower, and much more! It's like being on your own luxury houseboat!

5 out of 5 average rating, 16 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!

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!

4.97 out of 5 average rating, 224 reviews

Flat in Falmouth

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

4.94 out of 5 average rating, 125 reviews

Cozy 1-level fenced yard Craigville Beach 2000sqft

Welcome to Midori On The Cape! This freshly renovated 3-bedroom, 2-bath, Cape-style house features 2000 sq ft all in one level in a quiet neighborhood, 15000 sqft lot with fenced in flat backyard, fire pit, string lights, BBQ-grille. Quick access to Craigville Beach, Cape Cod Mall, vibrant Hyannis downtown and ferry terminal to Martha's Vineyard and Nantucket Island 2 living rooms, 2 dining areas, 3 super-sized bedrooms. Perfect for family staycation and gathering, get away.

Guest house 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.

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!

Guest house 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.

4.95 out of 5 average rating, 122 reviews

Flat in Barnstable

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!

5 out of 5 average rating, 165 reviews

Home in Marstons Mills

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

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

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Other great holiday rentals in Osterville, Barnstable

4.98 out of 5 average rating, 42 reviews

Private Lake Beach | Spectacular Views & Amenities

AndrewRating, 5 stars1 month ago

This is an absolutely beautiful rental and location. Cleanest, most pristine location we have been to. Appliances and bathrooms are glimmering. Host is immediately responsive and kind. 10 out of 10 in all respects.

4.81 out of 5 average rating, 16 reviews

Pristine Osterville Cottage

LuciaRating, 5 stars2 weeks ago

We had a lovely stay here! Matthew’s home was perfect, with a fenced in back yard that our dog absolutely loved running around in. The home is located in a beautiful peaceful neighborhood, close to beaches, and less than a 15 min walk to town where we had great coffee and breakfast. Would recommend staying here!

Guest suite in Marstons Mills

4.97 out of 5 average rating, 161 reviews

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

ChelseaRating, 5 stars9 months ago

My family had an amazing time! It was lovely and cozy. Peter +Jane were wonderful and responsive. They provided all the necessary things and then some. The place is very family friendly and my kiddos loved the backyard. Would recommend to anyone looking for a great time!

Guest house in Barnstable

4.95 out of 5 average rating, 78 reviews

Romantic getaway in historic Barnstable village.

Vicki AnnRating, 5 stars2 weeks ago

Our stay at Nichola’s far exceeded our expectations. The accommodation was very well equipped, clean and very comfortable. We will definitely stay at Nichola’s again.

5 out of 5 average rating, 17 reviews

Cottage in Barnstable

"Snug" cottage near town, pond and ocean beaches.

MattRating, 5 stars9 months ago

Loved our stay at the Snug. It was the perfect space and location to stay with our little family of 3. Nancy was very helpful, kind and responsive. The place was spotless, rooms were more spacious than expected, and the outdoor area feels like a private little getaway. Ideal location and walkable to anything you want to do. 3 minute drive to local beaches. Highly recommend. Can’t wait to stay again next year!

4.97 out of 5 average rating, 37 reviews

Cozy ranch with private neighborhood beach

AngelaRating, 5 stars6 days ago

The home was lovely. The inside and outside were just as described in the pictures. The home had everything needed in the kitchen for cooking, although we chose to order food for delivery. The neighborhood was very quiet with friendly neighbors. The location was close to groceries and shopping—great locations for the ferries (Woodhole and Island Queen) to Martha's Vineyard. Although my stay was short, the accommodations were perfect! CONS: It was most challenging to navigate the channels on the TV's in the home. I would only recommend having a local channel guide available.

5 out of 5 average rating, 20 reviews

The Hyannis Hub | Walkable to Cape Cod Mall (<1mi)

MisziRating, 5 stars1 week ago

We had a wonderful stay at this beautiful home in Hyannis! Elle was an exceptional host—communication was clear, prompt, and friendly from start to finish. The house itself was spotless, stylish, and incredibly comfortable, offering everything we needed for a relaxing getaway. The location was great and the price was very reasonable for the quality of the home. Highly recommend and would definitely stay again! We’ll be back!!! Thank you