Holiday rentals in Osterville

Guest house 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.

5 out of 5 average rating, 5 reviews

Spacious Cape getaway near iconic Craigville Beach

Relax in this sunny Osterville home near village cafés and 3 beaches. The open main floor has a roomy living area and eat-in kitchen w/ two comfy bedrooms and a full bath. A finished lower level w/ private suite with bath, lounge, and laundry. Step outside to a yard with a dining table +patio, grill, outdoor shower, firepit with chairs. Sidewalks straight to town & 15 mins Craigsville beach bike ride; Hyannis and major routes are close by. PS4, Wi-Fi, beach gear, and BEACH parking pass included.

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

4.95 out of 5 average rating, 235 reviews

Cottage in Sandwich

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!

5 out of 5 average rating, 21 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!

4.93 out of 5 average rating, 130 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.

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!

Superhost

Home in Marstons Mills

4.88 out of 5 average rating, 145 reviews

The Mills Retreat- 3BR/2Bath - Beach pass included

-Spacious 3 bedroom / 2 bath home located on quiet cul-de-sac. -Large deck with patio set and grill on a private lot. -Barnstable Beach Pass included, valid at all Barnstable public beaches for 1 vehicle. -Central Air conditioning with 2 zones. -All TV's are Roku TV's in guest mode allowing you to use your own streaming apps. -Fast Wi-Fi for the whole family. -Large basement with TV which is great for kids. -Fully equipped kitchen -Full-size front loading washer & dryer.

Guest house 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 house 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.

4.95 out of 5 average rating, 123 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!