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

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!!!

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.

1-level fenced in yard Craigville Beach 2200sqft
Welcome to Midori On The Cape! 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.

Martha's Vineyard Getaway Cottage
Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

Steps to Cape Cod Private Beach!
Beach Read is steps to East Sandwich's Private Beach! This charming cottage has 1 bedroom and a sleeper sofa. It is the perfect size for a couple or small family looking for a Cape Cod getaway! Recent upgrades include flooring, renovated bathroom and brand new gas grill. Spend the day relaxing on the beach & the evening making smores over a beach bonfire. Located in Cape Cod's oldest town, it is only a short ride to Sandy Neck, Town Neck, shops, restaurants & Tree House Brewery.

Cozy garden retreat close to it all! Pet friendly
Come enjoy the cape from a private, dead-end road off Rt 28. 10-15 mins to beaches, 15 to Hyannis or Falmouth, 5 to Mashpee commons. Or, relax in a hammock in the privacy of the fully-fenced in wooded yard or by the fire pit. Family and dog friendly! 2 desks for WFH in separate rooms. -Heat/AC in every room -High speed Wifi : 200+ Mbps in all areas inside, 30+ Mbps from hammock -Smart speakers for in/outdoor use -Fire TV w/ Netflix, Disney+, etc -Working fireplace (in Winter)

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.

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*

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!
Popular amenities for outdoor seating rentals in Osterville
House rentals with outdoor seating

Quintessential Waterfront Historic Cottage

Mid-Century Modern home 5 minute walk to beach

Stylish home with beach pass, close to everything

*The Cozy Escape* | Historic South Coast Retreat

Cape Cod Getaway - 3BR/2BA Beach Pass Included

Vineyard Haven Walk to Ferry

Lakefront Spa Retreat • Hot Tub • King Bed • Dock

Water Front Pond House - 3 acre Cape Cod Sanctuary
Apartment rentals with outdoor seating

Songbird Studio- Secluded but close to everything!

Peace By The Bay

Spacious & bright, near beaches

Brand new! Whole apartment, huge tub, full kitchen

Cozy Large Private Pet Friendly Studio

⭐ Amazing Onset Getaway in the Starfish Suite

Apartment suite|Firepit|Private Deck|Pond Access

Your Private Garden
Apartment rentals with outdoor seating

Prime Location! Walk to ferry, beach & downtown.

Hidden Hideaway

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth

Oct + Nov Discount | Central | Private Balcony

A Spectacular. Walk to beach, town and harbor 20

The Sea Salt Studio - Steps to the Beach!

Short walk to the Beach and Downtown Hyannis!

#3 Seashore Studio, 300 yards to Glendon Beach
When is the best time to visit Osterville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $316 SGD | $316 SGD | $348 SGD | $322 SGD | $442 SGD | $569 SGD | $655 SGD | $695 SGD | $498 SGD | $442 SGD | $425 SGD | $474 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 with outdoor seating in Osterville

Total holiday rentals
Explore 90 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 2,650 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
90 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!
Destinations to explore
- Rentals with a fireplace Osterville
- Rentals with beach access Osterville
- Rentals with a firepit Osterville
- Rentals with a washing machine and dryer Osterville
- Rentals with a patio Osterville
- Family-friendly rentals Osterville
- Pet-friendly rentals Osterville
- Rentals with pools Osterville
- House rentals Osterville
- Rentals with outdoor seating Barnstable
- Rentals with outdoor seating Barnstable County
- Rentals with outdoor seating Massachusetts
- Rentals with outdoor seating United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Easton Beach
- Onset Beach
- Coast Guard Beach
- Second Beach
- The Breakers
- Pinehills Golf Club
- Sandy Neck Beach
- New Silver Beach
- South Shore Beach
- Lighthouse Beach
- Cahoon Hollow Beach
- Nickerson State Park
- Cape Cod Inflatable Park
- Popponesset Peninsula
- Sea Gull Beach
- Skaket Beach
- Race Point Beach
- Scusset Beach State Reservation




