Entire home

Now booking Summer 2026!! OAK BLUFFS 5 Bedroom/3 Bath/Central AC.

Waterfront holiday home with kitchen and patio

Overview
Amenities
Policies
Location

Exceptional

5 bedrooms3 bathroomsSleeps 102000 sq ft

Popular amenities

Dryer
Washer
Parking available
Kitchen
Barbecue grill
Air conditioning

Explore the area

Oak Bluffs, MA

Place, Oak Bluffs Harbor
‪6 min walk‬
Place, Oak Bluffs Town Beach
‪13 min walk‬
Place, Inkwell Beach
‪13 min walk‬
Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
‪15 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

Bedroom 3

1 Queen Bed

Bedroom 4

1 King Bed

Bedroom 5

1 Queen Bed

3 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Bathtub or shower · Toilet

Spaces

Deck or patio

Porch or lanai

Kitchen

Separate dining area

Garden

About this property

Now booking Summer 2026!! OAK BLUFFS 5 Bedroom/3 Bath/Central AC.

This is one summer school you won't want to miss!
Bright, airy, elegant home is perfect combination of past and present featuring great natural light, high tin ceilings and spacious rooms. Vintage detail fuses nicely with modern amenities like Central AC, 77" Smart HDTV and strong wifi signal throughout.
The house is ideally located in a quiet residential neighborhood but within walking distance of the ferry. A five minute walk brings you to the waterfront and/or center of town. Stroll through the famous gingerbread cottages on your way to the boutiques and restaurants that make Oak Bluffs such a unique spot. Take full advantage of Inkwell and Jetty beaches- both only 10 minute walk from the house or jump in the car to explore all that the island has to offer.
Aside from location, what makes this house truly unique is the unbeatable combination of indoor/outdoor living space.
Mahogany deck, private outdoor shower and landscaped lawn are ideal for outdoor summer activities like grilling and lawn games. Separating the deck from the main living area is an absolute gem of a screened-in porch that provides all the benefits of being outside while remaining indoors. This porch has a ton of character, is a great gathering spot and is sure to be a hit with everyone.
The house itself is well appointed and has a nice flow throughout. There are two bathrooms and two bedrooms on first floor.
- Bedroom 1 has a queen bed
- Bedroom 2 has twin beds and TV
Ornate staircase leads to the second floor which contains one bathroom and three bedrooms.
- Bedroom 3 has a king bed and great views of sunrise. TV
- Bedroom 4 also has great light and a queen bed. TV
- Bedroom 5 has a queen bed and great view of the sunset.
Another fun feature is a smaller screened-in porch on the front of the house-perfect for morning coffee and watching the world go by.....
Summer School is the perfect backdrop for your Vineyard adventure!

Add dates for prices

Amenities

Kitchen

Washing machine

Dryer

Free WiFi

Air conditioning

Outdoor space

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Kitchen
Washer
Dryer
Free WiFi

House Rules

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

Please strip all beds and leave all dirty linens and towels in bathrooms before checking out.

Please do not flush ANYTHING other than toilet paper in toilets as septic system cannot handle wipes etc (even those labeled flushable)

No more than 2 cars in driveway. Do not park on grass at any time. Make sure all trash is properly disposed of in bins located behind outdoor shower

Important information

You need to know

Extra-person charges may apply and vary depending on property policy

Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges

Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed

On-site parties or group events are strictly prohibited

Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip

Host has not indicated whether there is a smoke detector on the property

Property Registration Number C0293272210

About the area

Oak Bluffs

Located in Oak Bluffs, this holiday home is in the city centre and on the waterfront. Trinity Park Tabernacle and Cottage Museum are local landmarks, and some of the area's activities can be experienced at Woods Hole Ferry Terminal and Oak Bluffs Harbor. Flying Horses Carousel and Oak Bluffs Fishing Pier are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

View more Holiday homes in Oak Bluffs

Oak Bluffs, MA

What's nearby

Oak Bluffs Harbor - 6 min walk - 0.6 km
Circuit Avenue - 6 min walk - 0.6 km
Oak Bluffs Town Beach - 13 min walk - 1.1 km
Oak Bluffs Ferry Terminal - 13 min walk - 1.1 km
Inkwell Beach - 13 min walk - 1.1 km

Getting around

Vineyard Haven, MA (MVY-Martha's Vineyard) - 15 min drive

Restaurants

‪The Barn Bowl & Bistro - ‬7 min walk
‪Nancy's - ‬8 min walk
‪Black Joy - ‬9 min walk
‪Offshore Ale Co. - ‬8 min walk
‪The Ritz Cafe - ‬9 min walk

Frequently asked questions

Is Now booking Summer 2026!! OAK BLUFFS 5 Bedroom/3 Bath/Central AC. pet-friendly?

No, pets are not allowed at this property.

Where is Now booking Summer 2026!! OAK BLUFFS 5 Bedroom/3 Bath/Central AC. located?

Located in the heart of Oak Bluffs, this holiday home is within a 15-minute walk of Oak Bluffs Public Library and Inkwell Beach. Trinity Park Tabernacle and Cottage Museum are also within 10 minutes.

About the host

Hosted by Finbarr Sheehan

We live in the Boston area, own a few rental properties and have fallen in love with the Vineyard and Summer School in particular. We love to travel whenever possible and rely on VRBO to help us find local and insider homes in amazing destinations. We hope you enjoy this house as much as we do and make it part of your annual Vineyard adventure.

Why they chose this property

This antique home, built in the late 1800's is filled with so much love and amazing energy. You can tell that all of its past owners have treated it with respect and honored all of the original details as best as they could, while embracing modern comforts. You will continually find ornate details within the home. Throughout the day, as the light changes so does the mood of the home...from a cheery and bright morning to greet you to a glowing sunset and cozy quiet evening to help you relax after a fun filled day.
The back screened-in porch will most likely become your favorite room as it is the perfect extension of the living area allowing you to enjoy the summer breeze while being protected from the elements. One of the best features of this home is all of the sneaky and cozy nooks you can escape to. Whether it be at a desk in the upstairs bowed window, to the front screened in porch watching the world go by or a hammock chair hanging from the tree on the back deck...there are many options for you to find some space and tranquility. The king bedroom is the perfect spot for your morning coffee as you watch the amazing sunrises.

What makes this property unique

The amazing aspect about this location is you truly don't need a car! Don't let the quiet street fool you...you are a moment away from the famous Camp Meeting Association with its intricate gingerbread homes and performances. The ferry and town are about a 5 minute walk where you will find everything you are looking for from great restaurants to adorable boutiques and food markets. The famous Inkwell Beach and Jetty Beach are about a 10 minute walk.