Holiday houses in Osterville

Historic Home in Prime Village Location: Sleeps 6

Welcome to Main Street House - a classic Cape Cod gambrel-style home built in 1905 & located steps away from the village center. Just restored to offer modern conveniences like central AC & a chef's kitchen - while preserving historical charm. The 3 BR, 1 bath home is equipped with luxury mattresses & linens, with high end modern finishes & vintage accents. A large patio boasts an outdoor living room, dining area, & oversized outdoor shower. Beach pass included - Dowses Beach is a ½ mile away.

Three Ships Cove | Walk to Craigville Beach

Welcome to Three Ships Cove! A brand-new, sun-filled Cape Cod cottage tucked away on a private cul-de-sac and just a short walk to Craigville Beach. Spend your days by the ocean, grab a cone from the iconic Four Seas Ice Cream, then enjoy dinner, shopping, or a concert at the Melody Tent—all within 10 minutes. Featuring 3 bedrooms, 2.5 baths, 2 living areas, and a beautiful outdoor space for morning coffee or evening cocktails, it's the perfect blend of comfort, convenience, and coastal charm.

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!

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/ 2 comfy bedrooms and a full bath. A finished lower level + private suite with bath, lounge, and laundry. Step outside to a yard with a dining table +patio, grill, outdoor shower, firepit with chairs. 4 adult bikes will get you straight to town & 15 mins beach ride; Hyannis and major routes are close by. PS4, Wi-Fi, beach gear, and BEACH parking pass included.

3BR Cape Cottage | Pergola & Gas Fire Pit

Welcome to your cozy beach retreat! Forget fighting for parking; this newly renovated and well-designed cottage is the perfect spot for a small family or friends seeking a comfortable and supremely convenient getaway. You are literally across the street from Craigville Beach, meaning you can walk over in seconds for sunrise, a mid-day swim, or sunset. Situated in a small compound with five other cottages, this home offers privacy with the benefit of a well-maintained community atmosphere.

Pristine Osterville Cottage

This is a newly renovated cottage in Osterville’s “golden triangle.” It is approximately a half mile from the town center and 1.3 miles from Dowses Beach. You will have a guest parking pass, which you can use for Dowses Beach or any other beach in Barnstable. The home features a large deck with a fenced-in backyard, gas grill, and outdoor shower. The kitchen is equipped with whatever you could need, including a Keurig and French press with grinder. The interior is modern and bright.

4 bedroom Cape in private neighborhood

Bright, beach decor and an open floor plan greet you in this centrally located Cape home with countless amenities. Located in the village of Osterville, you will be less than 2 miles from the town's acclaimed Dowses Beach, a mile from the quaint shops and restaurants downtown, and a 15 minute ride to Hyannis featuring beaches, a lively downtown, and ferries to Nantucket and Martha’s Vineyard. Suitable for adults and children alike, make this your home away from home during your stay.

Perfectly situated home in beautiful Osterville

Perfect home for families and couples. Two first floor master bedrooms with private new en-suite bathrooms. A spacious second floor bedroom with four twin beds. Central air and hardwood floors throughout. Large yard with mature gardens, deck, and outdoor dining table. Access to one of the Cape’s finest beaches with the landlord pass to private Dowses Beach. Walk into town to the upscale Main Street dining and shops of Osterville Village. We’re happy to have you any time of year.

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!

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.

Private Waterfront Escape | Kayaks + Firepit

🌊 Waterfront Cape Cod Escape | Beach Pass Included Wake up to ocean views, walk to the shoreline, and spend your days exploring Cape Cod’s best beaches—with your included Barnstable Beach Pass. Unwind on your private patio, gather around the firepit at night, and enjoy a peaceful coastal retreat designed for comfort and connection. Perfect for families, couples, and small groups looking for a relaxing, high-quality Cape Cod stay.

Hyannis 3BR Firepit Beach nearby

A beautifully maintained home designed for comfort, relaxation, and unforgettable memories. Whether you're exploring the coastline, enjoying peaceful mornings by the water, or gathering with family and friends, this home offers the ideal balance of location, amenities, and experience.