Oak Bluffs holiday homes

We found 1,941 holiday rentals — enter your dates for availability
Discover a selection of 271 homes, 36 apartments and other holiday rentals in Oak Bluffs that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as parking and a hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Oak Bluffs

Showing deals for:9 Oct - 16 Oct

Image gallery for The Park Estate: Oak Bluffs getaway

Exterior
9.8 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)

The Park Estate: Oak Bluffs getaway

Oak Bluffs

9% off
Price is NZ$98,378
for 7 nights, 1 home
NZ$14,054 per night
includes taxes & fees
The Park Estate: Oak Bluffs getaway

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Oak Bluffs

  • Scenic coastal charm: Enjoy picturesque seaside views, sandy town beach, and tranquil strolls along historic streets.
  • Historic lighthouse: Explore the iconic local lighthouse and immerse yourself in maritime history.
  • Outdoor adventures: Engage in beachside activities and leisurely walks that showcase the natural beauty of the coast.
  • Local culture: Experience a genuine coastal community vibe with charming neighbourhoods and vibrant local life.
  • Relaxing retreats: Discover peaceful spots perfect for unwinding and enjoying a laid-back holiday atmosphere.

Top attractions near Oak Bluffs

Oak Bluffs offers a delightful mix of outdoor and cultural experiences, ideal for New Zealand travellers seeking a beach and scenic retreat. Enjoy leisurely strolls along historic streets, explore the charming historic lighthouse, and take in the coastal views. With plenty of outdoor activities on offer, this picturesque coastal city ensures a memorable holiday experience filled with natural beauty and local charm.

Things to do recommended for couples

Explore Oak Bluffs hand-in-hand with your partner. Discover charming local eateries and scenic harbour walks, perfect for a romantic retreat. Enjoy the local culture and maritime history for a memorable Kiwi getaway.

Things to do recommended for families

Families visiting Oak Bluffs can explore the colourful streets, enjoy delightful rides on the carousel, and discover the local history at the Museum of Oak Bluffs, all offering a memorable New Zealand-style family adventure.

Things to do recommended for groups

Groups visiting Oak Bluffs can explore colourful local festivals, take scenic bike rides along coastal paths, and enjoy community picnics in charming town parks, capturing the essence of American New England hospitality with a Kiwi twist.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Oak Bluffs

Whether you're journeying with a group, as a family, with your pets, or seeking extended stays, be sure to apply the appropriate filters. Here are some Vrbo booking tips for you.

  • Traveling to Oak Bluffs with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Oak Bluffs with young kids: Traveling with little ones can be a challenge. You have to ensure their comfort and safety, as well as access to age-appropriate facilities like a private swimming pool. It’s also wise to consider how close you are to attractions that suit families.
  • Taking your pets with you to Oak Bluffs: For many travellers, a family holiday isn’t complete without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring everyone feels at home.
  • Planning for a long term stay visiting Oak Bluffs: If you're seeking holiday rentals with offers for stays of a month or more, you've come to the right place. With the appropriate filter, you can effortlessly locate and save on monthly rentals. Consider including a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Oak Bluffs

Oak Bluffs offers a delightful blend of beach and outdoor experiences. Enjoy the scenic town beach and relax amidst inviting seaside views. The town’s friendly atmosphere and vibrant local culture make it perfect for a tranquil yet engaging holiday. Discover charming neighbourhoods and picturesque spots that capture the essence of a true coastal retreat in Oak Bluffs, Massachusetts.

  • Martha's Vineyard: This enchanting island, a short 11km journey from Oak Bluffs, is a haven for nature lovers. With its pristine beaches, captivating outdoor scenery, and a laid-back vibe, it offers an ideal escape for those looking to relax and explore. Enjoy a variety of activities – from lively music concerts and a round of golf at a local course to simply unwinding by the shore at one of the family-friendly beaches. The delightful cape area provides a picturesque backdrop for memorable seaside strolls and scenic views.
  • Falmouth: Located 11km away from Oak Bluffs, Falmouth is a charming city that perfectly blends a coastal retreat with a touch of sophistication. Its sun-kissed beaches and expansive outdoor settings make it a prime destination for travellers seeking a mix of leisure and activities. Whether you fancy a round of golf, a visit to an educational centre, or a day out at a private country club, Falmouth caters to diverse interests. The local landmarks, including its famous family beaches and cape, add to its allure and provide a scenic setting for exploration.
  • Edgartown: Just 8km from Oak Bluffs, Edgartown radiates a refined seaside charm. This city captures the essence of a coastal escape with its inviting beaches and breathtaking outdoor landscapes. A favourite among visitors, the area offers an assortment of activities – from a challenging golf course to exploring bustling shopping areas. The family-oriented beaches and the picturesque cape nearby further enhance Edgartown’s appeal, making it a must-visit destination for those keen on experiencing classic seaside beauty.

Best time to go to Oak Bluffs

If you're planning a trip to Oak Bluffs, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.1°F (1.7°C)Light RainMostly SunnyAverage
February35.1°F (1.7°C)Light RainMostly CloudyAverage
March38.8°F (3.8°C)Light RainMostly SunnyAverage
April46.4°F (8.0°C)Light RainMostly SunnyAverage
May54.5°F (12.5°C)Light RainMostly SunnyAverage
June63.0°F (17.2°C)Light RainMostly SunnyHigh
July71.1°F (21.7°C)Light RainMostly SunnyHigh
August71.6°F (22.0°C)Light RainMostly SunnyHigh
September66.6°F (19.2°C)Light RainMostly SunnyAverage
October58.5°F (14.7°C)Light RainMostly SunnyLow
November48.9°F (9.4°C)Light RainMostly SunnyLow
December41.4°F (5.2°C)Light RainMostly SunnyLow

Booking with Vrbo is a breeze

Are you looking to save on your next holiday? Consider keeping your travel dates flexible, as prices can fluctuate. Additionally, staying longer could lead to significant savings. To find the ideal Vrbo property that suits your budget, simply use our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy area where you can easily create new trips, resume planning where you left off, or simply review and organise your travel plans. Your saved or booked properties are neatly categorised under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Explore the beachside setting in Oak Bluffs

Enjoy the wineries and other features of Oak Bluffs. This walkable and scenic city is well known for its beaches, shopping and local tours. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Oak Bluffs

Are you hoping to find attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that makes Oak Bluffs a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Shining Sea Bikeway (9.2 mi / 14.8 km)
  • Cape Cod Country Club (11.5 mi / 18.5 km)
  • Farm Neck Golf Club (1.2 mi / 2 km)
  • Cape Cod Winery (8.6 mi / 13.8 km)
  • Falmouth Country Club (10 mi / 16.1 km)
  • Mashpee River Reservation (13.2 mi / 21.2 km)

Exploring the natural landscape of Oak Bluffs

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Oak Bluffs is a great place to get outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Ocean Park (0.3 mi / 0.5 km)
  • Oak Bluffs Town Beach (0.4 mi / 0.7 km)
  • Inkwell Beach (0.5 mi / 0.7 km)
  • Tisbury Town Beach (2 mi / 3.3 km)
  • Edgartown Beach (2.8 mi / 4.5 km)
  • Lighthouse Beach (4.8 mi / 7.7 km)

Seasonal weather in Oak Bluffs

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 20°C.

Transport to and around Oak Bluffs

The nearest airport is in Vineyard Haven, MA (MVY-Martha's Vineyard), located 5.2 mi (8.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Hyannis, MA (HYA-Barnstable Municipal), which is 20.5 mi (32.9 km) away.

Frequently asked questions

What is the best area to stay in Oak Bluffs when booking a holiday home?
Among the most sought-after neighbourhoods to get a holiday property in Oak Bluffs is Lagoon Heights. Find your perfect stay on Bookabach and experience this area just like a local.
What is the most popular type of holiday home accommodation in Oak Bluffs?
The most desirable types of holiday homes in Oak Bluffs are houses. After something a little different? Bookabach has a variety of options to match our guests' requirements, so you'll see holiday homes in all shapes and sizes. The ideal fit is waiting for you — snap up yours today.
How much does it cost to rent a holiday home in Oak Bluffs?
The average price for a holiday home in Oak Bluffs is determined by a number of factors, like length of stay, property type and season. Whether you're thinking about a sprawling villa with space for extended family or an apartment for just you and the kids, just add your dates of travel to find stays that offer great value.
How much does it cost to rent a beach house in Oak Bluffs?
The average price for a holiday home near the beach in Oak Bluffs depends on when you're visiting the area and the style and size of property you're looking for. You can find prices easily and quickly on Bookabach by entering your dates of travel. Then use our filters to choose the number of bedrooms and amenities that you require, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday homes in Oak Bluffs?
With 310 holiday homes that welcome four-legged guests, your furry buddy can also come along on your Oak Bluffs holiday. Use the filter tool to browse our pet-friendly holiday homes and find a holiday home that'll set tails wagging on Bookabach.
Can I rent a house with a pool in Oak Bluffs?
Pack your swimwear and inflatable unicorn, because there are 67 houses with a private pool in Oak Bluffs. Unwind at one of these terrific holiday homes and every day can be a pool day. Simply enter your travel dates into Bookabach, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular home amenities in Oak Bluffs?
When it comes to home amenities that guests are looking for in Oak Bluffs, tennis, a firepit and a chef are at the top of the list. With Bookabach holiday homes, you'll find options to fit your style and taste, whether you're going on a holiday with your partner, family members or even pets.
Are there large group holiday homes in Oak Bluffs?
You'll find 62 holiday homes in Oak Bluffs that can host 10 or more people. Whether you're organising a get-together with extended family or a celebration like a birthday, there's ample space to get your group together under the same roof.
Are there holiday homes in Oak Bluffs that welcome kids?
Bring the entire group together for a fun-packed adventure in Oak Bluffs at one of our 310 family-friendly holiday properties. These stays provide conveniences that are just perfect for getaways with children, such as full kitchens, living rooms and patios. Just click on the "Properties good for families" filter box and pick out your favourite.
What are the top attractions for families in Oak Bluffs?
Keeping the kids happy during your Oak Bluffs holiday is child's play with these top family-friendly attractions:

  • Inkwell Beach
  • Oak Bluffs Town Beach
  • Falmouth Heights Beach

Are there one-bedroom holiday homes in Oak Bluffs?
There are 30 one-bedroom properties in Oak Bluffs to select from. A one-bedroom holiday home is a great choice if it's only you and your partner or if you're travelling on your own. Add in more convenience, privacy and space compared to a hotel, and you've got the makings of a break to remember.
Can I find two-bedroom holiday homes in Oak Bluffs?
Gather your loved ones and experience complete comfort and privacy in one of the 59 two-bedroom holiday homes Oak Bluffs has to offer.
Are there holiday homes with WiFi in Oak Bluffs?
Whether you want to keep up with the headlines, make a video call or surf social media, there are 89 holiday homes with WiFi in Oak Bluffs. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.
How can I find holiday homes with air conditioning in Oak Bluffs?
There are 280 Bookabach holiday homes with air conditioning in Oak Bluffs providing that gentle, cool breeze and extra bit of comfort. Enter your preferred travel dates and then take advantage of our filters to find stays with air conditioning.
How old do you have to be to rent a holiday home in Oak Bluffs?
The age limit can differ across properties on Bookabach, so be sure to check the rules of the holiday home in Oak Bluffs you're considering. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Oak Bluffs for?
The amount of time you can stay in an Oak Bluffs holiday home for depends on each property. Just tap in your preferred travel dates to see options that offer long-term stays. They come with everything you need to make your extended trip more comfortable and convenient, such as kitchens and yards. Some holiday homes may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

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