Osterville holiday homes

We found 341 holiday rentals — enter your dates for availability
Discover a selection of 58 homes and other holiday rentals in Osterville that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Osterville

Showing deals for:18 Dec - 25 Dec

Private kitchen
Exterior
Room
Living area
Exceptional
(11 reviews)

Newly renovated Cottage Across the street from Craigville Beach.

Centerville

20% off
NZ$3,542
for 7 nights, 1 cottage
NZ$506 per night
includes taxes & fees
Newly renovated Cottage Across the street from Craigville Beach.
family room
Terrace/patio
dining room
kitchen
Exceptional
(34 reviews)

Cotuit Home with an Inground Pool less One Block from the Beach

Cotuit

8% off
NZ$22,670
for 7 nights, 1 home
NZ$3,239 per night
includes taxes & fees
Cotuit Home with an Inground Pool less One Block from the Beach
Interior
Room
Living area
Exterior
Exceptional
(98 reviews)

Unique oceanfront windmill with breathtaking views of Nantucket Sound.

Centerville

8% off
NZ$10,857
for 7 nights, 1 home
NZ$1,551 per night
includes taxes & fees
Unique oceanfront windmill with breathtaking views of Nantucket Sound.
Dining
Winter retreat
"Treehouse" sitting deck
Midway in historic Craigville Village
Exceptional
(7 reviews)

Unique Home in Woods near Craigville Beach, Centerville, Family

Centerville

8% off
NZ$7,152
for 7 nights, 1 home
NZ$1,022 per night
includes taxes & fees
Unique Home in Woods near Craigville Beach, Centerville, Family
Room
Living area
Terrace/patio
Dining
Exceptional
(13 reviews)

Pristine Osterville Cottage

Osterville

7% off
NZ$5,020
for 7 nights, 1 home
NZ$717 per night
includes taxes & fees
Pristine Osterville Cottage
Private kitchen
Interior
Interior
Outdoor dining
Exceptional
(35 reviews)

Quiet private Centerville cottage, walk to beach, central A/C, parking pass.

Centerville

7% off
NZ$4,491
for 7 nights, 1 home
NZ$642 per night
includes taxes & fees
Quiet private Centerville cottage, walk to beach, central A/C, parking pass.
Room
Property grounds
Property grounds
Living area
Exceptional
(9 reviews)

Family-friendly hidden gem near Craigville Beach

Hyannis

11% off
NZ$3,620
for 7 nights, 1 home
NZ$517 per night
includes taxes & fees
Family-friendly hidden gem near Craigville Beach
Exterior
Interior
Private kitchen
Living area
Very good
(36 reviews)

Walk to the Beach!!!

Centerville

7% off
NZ$4,740
for 7 nights, 1 home
NZ$677 per night
includes taxes & fees
Walk to the Beach!!!
Room
Private kitchen
Dining
Outdoor dining
Exceptional
(19 reviews)

Serene Haven w/ No Shared Spaces | Cape Cod

Marstons Mills

8% off
NZ$3,979
for 7 nights, 1 apartment
NZ$568 per night
includes taxes & fees
Serene Haven w/ No Shared Spaces | Cape Cod
Outdoor shower
Front of the house
Living area
Private kitchen
Exceptional
(81 reviews)

Family - friendly home 1.5 miles to Craigville Beach (Beach pass Inc.)

Hyannis

8% off
NZ$2,924
for 7 nights, 1 home
NZ$418 per night
includes taxes & fees
Family - friendly home 1.5 miles to Craigville Beach (Beach pass Inc.)

Find the perfect holiday rental for your Osterville getaway

Learn about the unique charm of Osterville with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Osterville

Are you hoping to find things to do in the area? Venture out of your cosy holiday rental and experience everything that Osterville has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Cape Codder Water Park (5 mi / 8.1 km)
  • Cape Cod Inflatable Park (8 mi / 12.9 km)
  • Shining Sea Bikeway (13.1 mi / 21.2 km)
  • Cape Cod Baseball & Bumper Boats (15.4 mi / 24.8 km)
  • Cape Cod Lavender Farm (16.4 mi / 26.4 km)
  • Water Wizz (16.6 mi / 26.7 km)

Exploring the natural landscape of Osterville

Whether you're an adventurous traveller or just want to appreciate the scenery, Osterville is a great spot to appreciate mother nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Craigville Beach (2.5 mi / 4 km)
  • Popponesset Beach (5.4 mi / 8.7 km)
  • Kalmus Beach (5.8 mi / 9.3 km)
  • Hyannis Harbor (5.8 mi / 9.4 km)
  • Lewis Bay (6.5 mi / 10.5 km)
  • Barnstable Harbor (7.3 mi / 11.8 km)

Transport to and around Osterville

The nearest airport is in Hyannis, MA (HYA-Barnstable Municipal), located 5.8 mi (9.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Vineyard Haven, MA (MVY-Martha's Vineyard), which is 20.2 mi (32.5 km) away.

Frequently asked questions

What is the best area to stay in Osterville when booking a holiday rental?
When considering a holiday rental in Osterville, Massachusetts, a popular area to stay is near the charming village centre. This picturesque neighbourhood boasts a delightful array of boutique shops, cafes, and restaurants, making it an ideal spot for those who enjoy being close to local amenities. The village is also renowned for its beautiful beaches, such as Dowses Beach, where visitors can relax and soak up the sun or engage in water activities.Another appealing area is near the North Bay, which offers stunning waterfront views and a tranquil atmosphere. This part of Osterville is superb for those looking to enjoy nature, with opportunities for boating and fishing right at your doorstep. The proximity to the Osterville Historical Museum adds a cultural touch, allowing guests to explore the rich history of the area.Overall, Osterville features a selection of attractive properties ranging from charming cottages to more spacious homes.
Where are the best areas for renting a beach house in Osterville?
For renting a beach house in Osterville, Massachusetts, the area around Osterville Village is particularly appealing. This charming village offers a selection of holiday rentals that are close to the sandy shores of Dowses Beach, where visitors can enjoy swimming, sunbathing, and picturesque sunsets. Many properties in this vicinity come equipped with amenities such as private outdoor spaces, barbecue grills, and fully stocked kitchens, superb for family gatherings or friend getaways.Additionally, properties along the coastline often feature stunning views of Osterville Bay, with some offering direct access to the beach or nearby nature trails. Rentals may include spacious living areas, air conditioning, and outdoor showers to rinse off after a day at the beach.For those who enjoy a more tranquil setting, the area around Sampson's Island provides serene waterfront properties where guests can relax and unwind. These rentals typically offer amenities like kayaks or paddleboards, enabling easy exploration of the surrounding waters. The close proximity to local shops and restaurants in Osterville Village adds to the convenience, allowing visitors to enjoy the local cuisine and culture.
What is the most popular type of holiday rental accomodation in Osterville?
In Osterville, holiday houses are the most popular type of holiday rental, with approximately 236 available throughout the charming coastal community. These homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor areas for barbecues or relaxing in the sun. Many are situated near picturesque beaches and local attractions, providing easy access to the waterfront and recreational activities. Additionally, there are around 20 cottages available, which offer a quaint, cosy atmosphere great for couples or small families. These cottages often come equipped with essential amenities and are located in tranquil settings, making them an inviting option for a peaceful getaway.
Are there any family house rentals in Osterville?
In Osterville, there is a wealth of family-friendly house rentals to choose from, with around 47 properties available. This charming village, located on Cape Cod, offers a serene atmosphere superb for family gatherings. Many homes feature spacious living areas, fully equipped kitchens ideal for family meals, and outdoor patios or decks where children can play and families can enjoy al fresco dining.Visitors can explore nearby attractions such as Dowses Beach, which provides a beautiful spot for swimming and sunbathing, or take a stroll along the scenic waterfront. Additionally, the village is close to the lively town of Barnstable, where local shops and restaurants abound.
Can I rent a holiday home with a pool or hot tub in Osterville?
In Osterville, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs, with around 14 options to choose from. This charming coastal village offers a serene atmosphere, superb for a relaxing getaway. Many of these properties come equipped with private swimming pools, hot tubs, and spacious outdoor patios, allowing guests to enjoy the beautiful surroundings while soaking up the sun.Travellers can expect amenities such as fully equipped kitchens for preparing family meals, comfortable living spaces, and often, proximity to local beaches and marinas. Some rentals may also include features like fire pits for evening gatherings, outdoor dining areas, and lush gardens, enhancing the overall experience.
Are there pet-friendly house rentals in Osterville?
In Osterville, there are several pet-friendly house rentals available, providing a fantastic opportunity for travellers looking to enjoy a coastal getaway with their furry companions. Many of these holiday homes feature modern amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like patios or gardens, superb for pets to roam.The area is known for its charming atmosphere and proximity to beautiful beaches, making it an ideal destination for pet owners. Nearby, you can find local parks and nature trails where dogs can enjoy walks and playtime. Additionally, the scenic coastline and the tranquil waters of Nantucket Sound offer plenty of opportunities for outdoor activities, including dog-friendly beach access in designated areas.
Are there any remote work holiday rentals in Osterville?
In Osterville, Massachusetts, there is a substantial selection of remote work holiday rentals available, with around 256 options to choose from. This charming coastal village offers a serene environment conducive to productivity, with many properties equipped with essential amenities for remote workers. Travellers can expect to find high-speed internet, free Wi-Fi in rooms, and dedicated desk spaces, ensuring a comfortable working arrangement.The area is known for its picturesque beaches and vibrant local culture, with nearby points of interest including the charming shops and restaurants of Osterville Village. Many rentals also offer inviting living spaces, ideal for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Osterville?
In Osterville, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature outdoor spaces such as decks or patios, superb for enjoying the pleasant coastal weather. Onsite parking is commonly available, making it convenient for those travelling with a vehicle. Additionally, holiday rentals often provide coffee and tea makers, suiting guests' needs for a comforting morning beverage.
When is the best time to visit Osterville for a holiday rental?
The most popular time to visit Osterville for a holiday rental is during the summer months, particularly in July. This peak season, which runs from June to August, attracts a vibrant mix of families and beachgoers eager to soak up the sun along Cape Cod's beautiful shores. With warm temperatures averaging around 20 to 30 degrees Celsius, it's an ideal time for outdoor activities such as swimming, sailing, and exploring the picturesque coastline.While July is bustling with visitors enjoying everything from local seafood festivals to beach picnics, you might also consider November as a wonderful alternative for a more tranquil experience. This off-peak month offers a quieter atmosphere where you can appreciate the serene beauty of Osterville, ideal for leisurely walks by the beach and enjoying the crisp autumn air.For those who value comfort, the summer months provide not only a lively outdoor scene but also an array of charming holiday rentals equipped with modern amenities. Whether you're planning a family getaway or a romantic retreat, you'll find plenty of options that deliver both quality and convenience.In summary, if you're after the vibrant summer experience filled with activities and a lively community, July is your month.
What are the top attractions in Osterville?
In Osterville, visitors can enjoy a charming coastal experience with a focus on its lovely beaches and local culture. Dowses Beach, known for its soft sands and calm waters, is a popular spot for families and sunbathers alike. Nearby, the village centre offers quaint shops and eateries where travellers can savour local seafood and enjoy the picturesque surroundings.For those interested in maritime activities, the Osterville Marina provides opportunities for boating and fishing. Additionally, the nearby Cape Cod Museum of Natural History in Brewster, just a short drive away, offers educational exhibits and beautiful walking trails through the area's natural landscapes.
Are all fees included in the Osterville holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Osterville holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Osterville with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Osterville holiday homes?
You can find great discounts on holiday homes in Osterville on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Osterville holiday home booking on Bookabach?
To find Osterville holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Osterville?
A long-stay holiday home in Osterville is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Osterville holiday home?
Book your Osterville holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Osterville?
Prices for holiday homes in Osterville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Osterville to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.