
House holiday rentals in Osterville
Find and book unique houses on Airbnb
Quick stats about house rentals in Osterville

Total holiday rentals
Explore 140 holiday rentals in Osterville

Nightly prices starting at
Osterville holiday rentals start at €106 per night before taxes and fees

Verified guest reviews
Over 2,490 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
130 of Osterville holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Osterville rentals

4.9 Average rating
Osterville stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated house rentals in Osterville
Guests agree: these houses are highly rated for location, cleanliness and more.

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.
4.88 out of 5 average rating, 177 reviews
Cottage with private beach in Hyannis Port
Make your Cape Cod trip unforgettable in this Exclusive Harbor Village Cottage located right in Hyannis! Enjoy this recently updated 2-bed, 2-bath vacation home with access to private beach, beautiful outdoor deck, and peaceful ocean views. Follow the beach path 900 feet to the beach! Only minutes from downtown Main Street, the Melody Tent and Hyannis harbor. Whether you spend your days exploring the Cape, sunbathing on the beach, or relaxing on the deck, you will be sure to love this house!!!
4.91 out of 5 average rating, 232 reviews
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.
4.93 out of 5 average rating, 136 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
5.0 out of 5 average rating, 39 reviews
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.
5.0 out of 5 average rating, 249 reviews
Salt Eire | Oceanfront Beach Home
Welcome to Salt Eire. Steps to the beach for your morning walks. The sound of waves lulling you to sleep. A place for family and friends to relax and create memories. Nestled in the dunes of East Sandwich beach sits this oceanfront property (bay side) with stunning 360-degree views of Cape Cod Bay and Scorton Creek. Spend your days sunning and swimming before you return home to this comfortably appointed house. Also check out our new sister property down the road @ApresSeaCapeCod
4.99 out of 5 average rating, 158 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!
4.97 out of 5 average rating, 71 reviews
Private Pond-side Cape Cod Home
Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.
5.0 out of 5 average rating, 172 reviews
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*
4.83 out of 5 average rating, 199 reviews
Luxury House 0.25 mi from Craigville Beach
Welcome to Beyond the Beach Cape Cod in beautiful Centerville; close to Hyannis! During these uncertain times, be assured that we are taking every precaution available to us to ensure the health and safety of our guests. We are instituting enhanced cleaning of all sheets, mattress protectors and pillow protectors and quilts prior to each rental. After each stay we empty, clean and refill the outdoor hot-tub, which is available for your use year-round!
4.98 out of 5 average rating, 172 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!
5.0 out of 5 average rating, 233 reviews
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!
4.96 out of 5 average rating, 104 reviewsPopular amenities for house rentals in Osterville
House rentals with a pool

"Cape Escape" luxury home w/pool & beach access.
4.99 out of 5 average rating, 103 reviews
Private Pool, near beaches, 3 BR/3 BA, Central Air
4.96 out of 5 average rating, 146 reviews
Swing Set, Plunge pool, and large yard await!
4.76 out of 5 average rating, 37 reviews
In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!
4.8 out of 5 average rating, 49 reviews
Upscale Secluded Home w/Central AC, Pool & Firepit
4.94 out of 5 average rating, 16 reviews
ShoestringBayHouse, waterfront & pool in Cotuit
4.97 out of 5 average rating, 32 reviews
Coastal Charm New Seabury: 5BRs with Private Pool
4.94 out of 5 average rating, 53 reviews
Beach Pass Included! Brand New Spa! Central AC!
4.97 out of 5 average rating, 32 reviewsWeekly house rentals

Perfectly situated home in beautiful Osterville
4.9 out of 5 average rating, 60 reviews
Newly Renovated Cape, walk to Osterville
4.98 out of 5 average rating, 44 reviews
4 bedroom Cape in private neighborhood
4.98 out of 5 average rating, 48 reviews
Pristine Osterville Cottage
4.9 out of 5 average rating, 31 reviews
Historic Home in Prime Village Location: Sleeps 6
5.0 out of 5 average rating, 17 reviews
Private Waterfront Escape | Kayaks + Firepit
4.94 out of 5 average rating, 16 reviews
Spacious Cape getaway near iconic Craigville Beach
4.88 out of 5 average rating, 25 reviews
Three Ships Cove | Walk to Craigville Beach
4.99 out of 5 average rating, 77 reviewsPrivate house rentals

Mariners Mills- Craigville beach / Joshua Pond
4.74 out of 5 average rating, 23 reviews
Spacious Home w/ Beach Pass & Private Pond Access
4.93 out of 5 average rating, 28 reviews
Beachfront Ocean Views from Every Room
4.99 out of 5 average rating, 81 reviews
New construction, Near Craigville Beach & Main St.
4.96 out of 5 average rating, 54 reviews
Osterville House on the Hill! Beach Pass included!
4.91 out of 5 average rating, 22 reviews
Cozy ranch with private neighborhood beach
4.97 out of 5 average rating, 65 reviews
Lovely, Spacious Cottage near Craigville beach
4.82 out of 5 average rating, 57 reviews
Waterfront! Swan's Retreat. Steps to C'ville Beach
4.83 out of 5 average rating, 42 reviewsDestinations to explore
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Onset Beach
- East Sandwich Beach
- Duxbury Beach
- Sandy Neck Beach
- Saquish Beach
- Easton Beach
- Nauset Beach
- New Silver Beach
- Skaket Beach
- Popponesset Peninsula
- Cape Cod Canal
- Falmouth Heights Beach
- Pinehills Golf Club
- Inkwell Beach
- Race Point Beach
- The Breakers
- Second Beach
- Coast Guard Beach
- Cape Cod Inflatable Park
- Easton's Beach





