House vacation rentals in Osterville

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Top-rated house rentals in Osterville

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favourite
An outdoor dining setting features a table with a plate of salad and wine glasses, accompanied by a bottle of white wine. In the background, a charming shed displays ‘Cape Away’ signage, surrounded by well-maintained greenery and a cozy lounge area.
Home in South Yarmouth
5 out of 5 average rating, 178 reviews

Relaxing Retreat | King Beds * Sauna * Bar Shed

Welcome to Cape Away, your charming family & pet-friendly retreat! Enjoy a fully stocked kitchen, cozy fireplaces, sauna, and outdoor shower. Unwind with dozens of board games, dart board, fire pit, and BBQ. The fully fenced private backyard offers beach gear, a bar shed and lounge area. We are perfectly located just 5–20 minutes from top rated restaurants and beaches, making it your ideal home base. With premium amenities, thoughtful touches it’s the perfect space to escape, explore and relax.

Top guest favourite
A charming cottage is surrounded by lush greenery and soft landscaping. The exterior features a light wood shingle design with a welcoming porch and a shaded deck area. Outdoor seating is present, inviting relaxation under the clear blue sky.
Home in Hyannis Port
4.9 out of 5 average rating, 191 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!!!

Top guest favourite
The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.
Home in Cotuit
4.95 out of 5 average rating, 128 reviews

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!

Guest favourite
The exterior of a two-story residential building is displayed, featuring light gray siding and dark blue shutters. A well-maintained lawn surrounds the home, complemented by two coniferous trees and various shrubs. The entrance is marked by a solid black door, enhancing the home’s facade.
Home in Barnstable
4.92 out of 5 average rating, 97 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.

Top guest favourite
A quaint historic home features classic shingle siding and a welcoming green front door. Windows with evenly spaced panes provide a glimpse of the interior, while a white picket fence and lush greenery frame the property, creating an inviting setting.
Home in Sandwich
5 out of 5 average rating, 221 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.

Guest favourite
A modern dining area is presented with a light wooden table surrounded by yellow chairs and a long bench. A vibrant, multicolored rug lies underneath, and a bouquet of flowers sits at the center. A tall green plant adds a refreshing touch to the space.
Home in Barnstable
4.98 out of 5 average rating, 101 reviews

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!

Guest favourite
A bright living room features light blue walls and hardwood flooring, with natural light streaming through skylights. A cozy seating area includes a grey sectional and a light-colored side table, while a fireplace is adorned with decorative art. A television is positioned across from the seating arrangement.
Home in Barnstable
4.89 out of 5 average rating, 151 reviews

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.

Guest favourite
Home in Marstons Mills
4.89 out of 5 average rating, 155 reviews

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.

Top guest favourite
A spacious living room features modern furnishings arranged for comfort. A large flat-screen TV is mounted above an electric fireplace. Natural light enters through multiple windows, and a playful dog portrait decorates the wall. A patterned rug anchors the seating area.
Home in Falmouth
4.98 out of 5 average rating, 330 reviews

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!

Guest favourite
The exterior of a charming Cape house is visible, featuring a light-colored shingle facade and a distinct triangular roof. A welcoming porch adorned with white latticework provides seating. The setting is enhanced by a clear blue sky, with nearby trees offering a touch of greenery.
Home in West Yarmouth
4.9 out of 5 average rating, 501 reviews

Beach House, Harbor View and Family Friendly.

Our house is a stones throw from the beach. The harbor, Hyannis, downtown, cafes, restaurants, anywhere from 5 star dining to family-friendly dining are all in walking distance. Several family friendly activities are very close. You’ll love our place because of the walk to the family friendly beach, the ambiance, the ocean view and the neighborhood feel. Our place is good for couples, solo adventurers, business travelers, fishermen, families (with kids) and large groups.

Top guest favourite
The exterior of a spacious coastal property is shown, featuring a wraparound porch and light grey shingle siding. A clear blue sky complements the beach setting, with soft sand leading to the ocean in the background. Lush greenery borders the property, providing a sense of seclusion.
Home in East Sandwich
4.99 out of 5 average rating, 145 reviews

*Oceanfront Beach Home*

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

Top guest favourite
An outdoor patio area is illuminated softly at dusk, featuring a dining set with a table and several chairs arranged on a patterned rug. Lush greenery and flowering plants surround the space, while lanterns provide a gentle glow, enhancing the tranquil environment.
Home in Mashpee Neck
5 out of 5 average rating, 195 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!

Popular amenities for Osterville house rentals

When is the best time to visit Osterville?

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Avg. price$491 CAD$491 CAD$456 CAD$463 CAD$519 CAD$681 CAD$772 CAD$807 CAD$562 CAD$421 CAD$461 CAD$491 CAD
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Quick stats about house rentals in Osterville

  • Total vacation rentals

    Explore 120 vacation rentals in Osterville

  • Nightly prices starting at

    Osterville vacation rentals start at $126 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,280 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    120 of Osterville vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Osterville rentals

  • 4.8 Average rating

    Osterville stays are highly rated by guests—averaging 4.8 out of 5!