
Holiday rentals in Osterville
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Osterville
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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.

Quaint Cape Cod Cottage on a Private Beach!
Create magical memories on the Cape at this sweet seaside cottage! A perfect place for a family-friendly getaway or a romantic retreat for two! The new contemporary coastal decor is cozy and comfortable and my place has all of the amenities you could want for your stay! Just steps to a beautiful beach with stunning sunsets and sunrises, cool ocean breeze, and the warm Nantucket Sound. Enjoy Popponesset Marketplace for food, shopping and fun or take a short drive to Mashpee Commons for more!

Romantic Cottage w/ Bikes, Paddle Boards & Kayaks
This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

Upper Cape Cozy Cottage
Simple but cozy cottage on an acre property next to the main house. Moderate sized bedroom and living room. Small kitchen and bathroom. The kitchen is fully equipped for cooking. Air conditioning is a portable unit and only in the bedroom. Games, books, and puzzles provided. There is no cable but a smart TV is included with access to Netflix etc. if you have an account. Outdoor area includes charcoal grill and seating . Large back yard with yard games, basketball hoop and fire pit.

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.

Beach Glass Cottage - Pond Front
Come stay at the Beach Glass Cottage! A pristine pond front, completely renovated and tastefully decorated, 3 bedroom, 2 bathroom cottage in the heart of Hyannis. Truly the perfect get-a-way for family and friends. The Beach Glass Cottage is tucked away from the action, but within walking distance to Main Street Hyannis, which features eclectic shops, restaurants, bars, ice cream with mini golf and the Cape Cod Melody Tent is a short walk from the cottage as well.

WOW LAKE VIEW! Waterfront with Beach, King Bed
Wake up to magnificent Panoramic Views of a Beautiful Lake with Waves Lapping below your Window! Scan the QR code to See a Full Video Tour on YouTube. Guests love its Stylish, Peaceful, Open Design; Wall-to-Wall, Floor-to-Ceiling Windows; Private Beach with Chaise Lounge Chairs; a Full, Modern Kitchen; Comfortable King hybrid gel/coil Bed; Private Office; Bathroom with Curved Shower; AC, and Much More! It's like being on your own Luxury Houseboat!

Your dog will love it here and you will too.
If you love to travel with your dog (dogs), like I do, then this is the perfect place for you and your dog. We have a large fenced in yard for your dog to play in and for you to relax in with your dog. We have a one bedroom apartment with a full kitchen, bath, living room and dining area When you book would you PLEASE let me know whether or not you will be traveling with a dog and if you are what breed of dog will you be bringing. Thanks!

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.

The Sea-Cret Garden, Guest Apartment
Kick back and relax in this calm, stylish space! This comfortable and peaceful guest apartment is situated in an ideal location in a quiet, beautiful neighborhood that is close to beaches and a short drive to downtown. Take a quick stroll to the West Falmouth Market or the Shining Sea Bike Path. With easy access to Chapoquoit & Old Silver Beach, this perfectly situated apartment is in an ideal spot for your next Falmouth getaway!

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!
Popular amenities for Osterville holiday rentals
Stay near Osterville's top sights
Other great holiday rentals in Osterville

Charming Cozy Coastal Retreat|Pet Friendly|EV

Newly Renovated 2000 sqft near Craigville Beach

Charming Barnstable Village Suite Close To Beach

Your Cape Escape! Close to Shopping mall and Beach

Spacious Cape getaway near iconic Craigville Beach

Bright beachy 2 kings. Linens/beach pass

Clean private & cozy Cape Cod 1 br/ba with kitchen

Charming Cape House with Private Hot Tub !
When is the best time to visit Osterville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $378 SGD | $378 SGD | $378 SGD | $395 SGD | $429 SGD | $541 SGD | $631 SGD | $652 SGD | $457 SGD | $378 SGD | $414 SGD | $441 SGD |
| Avg. temp | 0°C | 0°C | 3°C | 7°C | 12°C | 17°C | 21°C | 21°C | 18°C | 13°C | 8°C | 3°C |
Quick stats about holiday rentals in Osterville

Total holiday rentals
Explore 150 holiday rentals in Osterville

Nightly prices starting at
Osterville holiday rentals start at $101 SGD per night before taxes and fees

Verified guest reviews
Over 3,710 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 50 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
140 of Osterville holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Osterville rentals

4.9 Average rating
Osterville stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Rentals with a firepit Osterville
- Rentals with a patio Osterville
- House rentals Osterville
- Rentals with a fireplace Osterville
- Rentals with pools Osterville
- Pet-friendly rentals Osterville
- Family-friendly rentals Osterville
- Rentals with a washing machine and dryer Osterville
- Rentals with outdoor seating Osterville
- Rentals with beach access Osterville
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Easton Beach
- Onset Beach
- Second Beach
- Coast Guard Beach
- The Breakers
- Pinehills Golf Club
- South Shore Beach
- New Silver Beach
- Lighthouse Beach
- Sandy Neck Beach
- Nickerson State Park
- Cahoon Hollow Beach
- Cape Cod Inflatable Park
- Sea Gull Beach
- Popponesset Peninsula
- Scusset Beach State Reservation
- Race Point Beach
- Skaket Beach




