Family-friendly holiday rentals in Osterville

1-level fenced in yard Craigville Beach 2200sqft

*generator, solar panel backup powered*. 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.

Kitchen · Family · Amenities

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 6/20-9/15/26. The reviews tell all!

Family · Indoor spaces · Condition

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.

Indoor spaces · Family · Accuracy

Serene Haven w/ No Shared Spaces | Cape Cod

My peaceful 2-bedrooms, 1 bathroom residential private apartment (Entire Main Level) has everything you need for your Marstons Mills trip. The home comes with Wi-Fi, self-check-in, and free parking. During your stay, you will enjoy the privacy of zero shared spaces. Free cleaning once per week for stay 6 days or greater. Our Airbnb is within walking distance to eateries, gift shops, and other community staples. An ideal base to explore Marstons Mills, Cape, and Islands. Bring the whole family.

Kitchen · Indoor spaces · Value

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!

Kitchen · Indoor spaces · Grill

Quintessential Waterfront Historic Cottage

Set in a historic district and on a quiet pond shore, create memories with family and friends that will last a lifetime. Enjoy quintessential New England views from every angle. Coffee, restaurants, shopping & a fresh spring water fountain within a short walk to village center and under a mile to the nearest beach. Spend time walking the local area, exploring Cape Cod and relaxing in an atmospheric setting. Each room has been curated in a timeless tone, with relaxation and comfort in mind.

Family · Indoor spaces · Air conditioning

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.

Kitchen · Indoor spaces · Condition

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!

Family · Indoor spaces · Grill

Spacious house steps to Craigville beach! Dog ok!

Welcome to our Craigville retreat, close walk (0.3 mi) to one of the most beautiful beaches on the Cape. We are close to other beaches, ferry to Islands, food, hiking/kayaking/biking, Melody tent. You’ll love it because of the location and lots of natural light. If you want to stay in-enjoy private fenced backyard w/ fire pit, porch furniture and a hammock. Stocked with all you need to relax. We can host one dog. *Read/Agree to Pet policy bfr booking w dog*

Kitchen · Indoor spaces · Value

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.

Indoor spaces · Family · Back garden

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!

Family · Indoor spaces · Beach

Tranquil Cape Getaway 4BD/2BA with A/C, beach pass

Peaceful Cape Retreat Indulge in a serene holiday at this stunning, pristine 2-level Cape-inspired residence, featuring four cozy bedrooms and an expansive garden oasis! Complimentary beach access pass for all guests (Please send additional request after booking, extra deposit need) Gather your loved ones and create unforgettable moments at this idyllic haven!

Family · Kitchen · Check-in