
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.

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 6/20-9/15/24. The reviews tell all!

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.

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.

Cape Cod Beach House -Beach Pass Included!
Thoughtfully designed for travelers, by travelers, our relaxing beach bungalow is your perfect getaway! Relax & recharge while surrounded by gorgeous beaches with everything you need at your fingertips. Charming 2 bedroom home & peaceful yard within a quiet, centrally located neighborhood - hiking trails & beaches abound. Whether you’re staying for a weekend or a week, our comfortable home is the perfect spot for your Cape Cod getaway! Central Air, WiFi, Alexa & Beach Pass included too!

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.

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.

Cape Cod Getaway - 3BR/2BA Beach Pass Included
Spacious 3BR/2BA Cape Cod retreat on a quiet cul-de-sac in Barnstable. Perfect for families and groups, this home features a large deck with grill, Barnstable public Beach Pass (1 vehicle). Central A/C with 2 zones, Roku TVs in guest mode, fast Wi-Fi, and a fully equipped kitchen. Enjoy a kid-friendly basement with TV, plus full-size washer & dryer. Sleeps up to 8 with queen beds in every room. Ideal for a relaxing Cape Cod getaway, short drive to beaches, dining, and shops.

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)

The Driftwood Home, 5 min from Mashpee Commons, AC
- NOW PET FRIENDLY! - 15 min to Old Silver, South Cape, and Falmouth Heights beaches - 5 min to Mashpee Commons - 15 min to Falmouth Main St - 1600 square feet, built in 2014, w/ central AC - Large kitchen w/ all cookware and utensils - Outdoor deck with seating, fire pit, and grill - 55” Smart TV - 10 min to Shining Sea Bike Trail - Less than 10 min to Falmouth, Cape Cod, and Quashnet Valley Country Clubs - Centrally located to all of the Upper Cape - No parties or events!

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.

600 ft Walk to Ocean! 2nd floor Renovated Cottage!
Quaint second floor 785 sq ft unit w/ private entrance. 3 tenants MAX with ONE parking spot. 600 ft to shared neighborhood private beach. Great spot for couples or small families. NO guests without prior permission in house or on private beach. Queen bed in master, one twin bed in 2nd bedroom. Eat-in kitchen/living room. Bathroom w/ stand-up shower. Stocked w/ linens, towels, kitchen supplies. Island ferry boats - 1m. Historic Main St.- 1.2

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

Stylish home with beach pass, close to everything

Violet’s Place- king bed- pet friendly- hot tub!

Spacious Cape getaway near iconic Craigville Beach

Osterville- New Renovation, Central AC, Beach Pass

Spacious cottage beach Wychmere < 4 min Central AC

Osterville 4BR, Hot Tub, Beach Pass, Walk to Pond

Historic Home in Prime Village Location: Sleeps 6

Grill n’ Chill in Osterville | Classic Cape Codder
Apartment rentals with outdoor seating

Songbird Studio- Secluded but close to everything!

Cape Cod Beachfront 2 bedroom Cottage Harwich

Peace By The Bay

Brand new! Whole apartment, huge tub, full kitchen

Spacious & bright, near beaches

Top floor with views and steps to private beach

Cozy Large Private Pet Friendly Studio

⭐ Amazing Onset Getaway in the Starfish Suite
Apartment rentals with outdoor seating

Heart of downtown, walk to ferry, bikeway & beach!

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

Door to shore in a hop, skip, and a jump!

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

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 | $321 SGD | $321 SGD | $353 SGD | $327 SGD | $449 SGD | $577 SGD | $664 SGD | $706 SGD | $505 SGD | $335 SGD | $385 SGD | $437 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 $90 SGD per night before taxes and fees

Verified guest reviews
Over 2,570 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
- House rentals Osterville
- Rentals with beach access Osterville
- Rentals with a washing machine and dryer Osterville
- Rentals with a fireplace Osterville
- Family-friendly rentals Osterville
- Rentals with pools Osterville
- Rentals with a firepit Osterville
- Rentals with a patio Osterville
- Pet-friendly 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
- White Horse Beach
- Horseneck Beach State Reservation
- Second Beach
- Coast Guard Beach
- The Breakers
- Pinehills Golf Club
- Chapin Memorial Beach
- Island Park Beach
- Inman Road Beach
- South Shore Beach
- Nauset Beach
- Lighthouse Beach
- Minot Beach
- Town Neck Beach
- Ellis Landing Beach
- Linnell Landing Beach




