Vacation rentals in Osterville

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Top-rated vacation rentals in Osterville

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

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Guest favorite
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
4.88 out of 5 average rating, 160 reviews

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.

Top guest favorite
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 6/20-9/15/26. The reviews tell all!

Guest favorite
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
4.91 out of 5 average rating, 107 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 favorite
A two-story home with light blue siding and white trim is set amid lush greenery and flowering shrubs. A mailbox stands near the entrance, framed by well-maintained grass and colorful flower beds, enhancing the home's welcoming curb appeal.
Home in Barnstable
5 out of 5 average rating, 31 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

Guest favorite
A single-story ranch home is set among trees, featuring a stone pathway leading to a front door framed by multiple windows. A bench is positioned on the grassy lawn, adorned with colorful flowers adding life to the landscape.
Home in Barnstable
4.89 out of 5 average rating, 137 reviews

Stylish home with beach pass, close to everything

Modern home near Dowses and Craigville beach, Ropes and Loop beach (2.3 miles) with pass included for all ponds, lakes and beaches in Barnstablle. Beautiful 3 br ranch. Brand new Central AC and heating system, furniture, beds and kitchen appliances. Private fenced yard with deck, BBQ, fire pit, plenty of seating, outdoor shower. 2.5 mi to Joshua pond, North Pond- for fishing and Wequaquet Lake for swimming. Main st Hyannis restaurants and clubs, Cape Cod Mall. Fast internet, cable, smart TV.

Top guest favorite
A historic home features classic New England architecture, with a peaked roof and wooden shingle siding. White trim outlines the windows and door, while a white picket fence surrounds the property. Lush greenery and colorful flowers enhance the welcoming exterior under a clear blue sky.
Home in Sandwich
5 out of 5 average rating, 223 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 favorite
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!

Top guest favorite
Two lounge chairs are positioned around a low table, offering a clear view of Sam Pond. Lush greenery and trees frame the scene, providing a serene outdoor space. Lanterns are placed on the table, adding a subtle touch to the inviting patio.
Home in Barnstable
4.97 out of 5 average rating, 63 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!

Top guest favorite
A charming two-story home is framed by vibrant greenery and colorful shrubs, with a paved pathway leading to the entrance. Solar panels adorn the roof, reflecting a commitment to sustainability. Lush grass and well-maintained landscaping create an inviting atmosphere.
Home in Falmouth
5 out of 5 average rating, 160 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.

Top guest favorite
A bright living area features a striped couch adorned with a 'SUMMER HOUSE' pillow, complemented by a cozy armchair. Natural light enters through windows with white blinds, and wooden beams add a touch of character. A decorative coffee table sits in the center, enhancing the inviting space.
Guesthouse in Barnstable
4.9 out of 5 average rating, 70 reviews

Osterville Guest House

Charming 600 sq. ft. guesthouse located in the desirable village of Osterville. Take a short walk down Main Street for some shopping or dining. Along the way you may want to stop at Gone Chocolate for an ice cream or Dunkin Donuts for a quick coffee. You will have your choice of several restaurants to dine at including Five Bays Bistro, Crisp Flatbread Inc., Wimpy’s Seafood Market, or the newest restaurant in Osterville- the Chart Room at Crosby’s boat yard.

Top guest favorite
A welcoming living area features comfortable electric recliners and a small table, set against neutral-colored walls. A nautical-themed rug lies on the floor, while wall art and colorful flags add character. Natural light flows in through the window, which is adorned with blinds.
Tiny home in Mattapoisett
4.99 out of 5 average rating, 129 reviews

101 Steps to Beach/Island/Bike Path

Experience the Seaside Town of Mattapoisett. Location! Relax in this cozy cottage that is 101 steps from the front door to the Beach/Island/Bike Path. Enjoy this popular, sought after scenic Path for walking, biking, or a day at the Beach. The path is known for its picturesque coastal views. Walking distance to the Quaint Town, Shipyard Park, and many restaurants. Ned's Point Lighthouse- 5min. Day trip to the Vineyard? Ferry- 14 min. Season Open! 10% off wk!

Top guest favorite
The exterior of Salt Tide Cottage is shown, featuring a white-sided structure with a dark blue door and a large star decoration. A small seating area with two chairs and a table is positioned in front, surrounded by well-maintained green grass and trees.
Guesthouse in Craigville
4.89 out of 5 average rating, 157 reviews

Cottage in Centerville (BEACH PASS)

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.

Popular amenities for Osterville, Barnstable vacation rentals

When is the best time to visit Osterville?

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Quick stats about vacation rentals in Osterville

  • Total vacation rentals

    Explore 150 vacation rentals in Osterville

  • Nightly prices starting at

    Osterville vacation rentals start at € 69 per night before taxes and fees

  • Verified guest reviews

    Over 3,710 verified reviews to help you choose

  • Family-friendly vacation rentals

    130 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    140 of Osterville vacation rentals include wi-fi 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!