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

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Aerial view
Exterior
Exterior
Exterior
Exterior

Reviews

10 out of 10, Loved by Guests
Top 10% based on
5 bedrooms3 bathroomsSleeps 102000 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View in a map
Oak Bluffs, MA
  • Place, Oak Bluffs Harbor
    ‪6 min walk‬
  • Place, Circuit Avenue
    ‪6 min walk‬
  • Place, Inkwell Beach
    ‪13 min walk‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪17 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!

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House Rules

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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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 Oak Bluffs Harbor and Oak Bluffs Ferry Terminal. Flying Horses Carousel and Polly Hill Arboretum are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Oak Bluffs, MA

What's nearby

  • Oak Bluffs Harbor - 6 min walk - 0.6 km
  • Circuit Avenue - 6 min walk - 0.6 km
  • Ocean Park - 11 min walk - 1.0 km
  • Oak Bluffs Town Beach - 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

  • ‪Lookout Tavern - ‬11 min walk
  • ‪The Barn Bowl & Bistro - ‬7 min walk
  • ‪Offshore Ale Co. - ‬8 min walk
  • ‪Nancy's - ‬8 min walk
  • ‪Portuguese-American Club - ‬13 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.

How much does it cost to stay at Now booking Summer 2026!! OAK BLUFFS 5 Bedroom/3 Bath/Central AC.?

As of 13 Mar, 2026, prices found for a 1-night stay for 2 adults at Now booking Summer 2026!! OAK BLUFFS 5 Bedroom/3 Bath/Central AC. on 24 Apr, 2026 start from S$959, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Now booking Summer 2026!! OAK BLUFFS 5 Bedroom/3 Bath/Central AC.?

On-site parking is available at the 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 10-minute walk of Oak Bluffs Public Library, Trinity Park Tabernacle and Cottage Museum. Oak Bluffs Harbor and Circuit Avenue are also within 10 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 13 out of 13 reviews
Rating 8 - Good. 0 out of 13 reviews
Rating 6 - Okay. 0 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Antonette G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Off Season Vacation

House was lovely and perfect size for our gang of 8. Owner was quick to respond if we had questions. We truly enjoyed our stay and plan to be back!
Stayed 4 nights in May 2025

10/10 Excellent

Adrienne D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Trip

We had an enjoyable trip to OB this year. The house was spacious and the location was amazing. Would highly recommend this property.
Stayed 7 nights in Aug 2021

10/10 Excellent

Thomas D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome Property

Very nice home located a short walk to the center of Oak Bluffs. Plenty of space for the whole family with a wonderful outdoor porch for gathering.
Stayed 7 nights in Jul 2022

10/10 Excellent

Nancy A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our MV vacation 😊

Very nice home. Lots of space. Front deck is nice we sat there most nights. Beds and bedding very comfortable and luxurious. Overall everyone had a great time.
Stayed 7 nights in Aug 2024

10/10 Excellent

Pete K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family celebration

The house was perfect for a celebration to celebrate graduations, jobs, and health. The location was great for walking in to the Town or Oak Bluffs or to the beach. The house had plenty of space to spread out plus a ton of games and a huge TV which were perfect for a rainy day.
Stayed 4 nights in May 2021

10/10 Excellent

Pam S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect home and hosts

This home is large, comfortable, clean, and well appointed. It is a short walk (5 minutes, tops) to the main drag in OB, Inkwell Beach, and the marina. We cooked breakfast in most days, and the kitchen had everything we needed (and more). Having 2 washing machines and dryers was such a bonus. The beds were so comfortable that every one of our group of seven people had the best sleep every night. We will definitely be back!
Stayed 7 nights in Jul 2025

10/10 Excellent

Pete K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Summer School Refresher

We stayed at "Summer School" two years ago and this year's trip did not disappoint. The property is in a great location - walking distance to the shops, restaurants, and ferry in Oak Bluffs. The amenities are superb and the owner's keep making improvements. Plenty of room for the family to spread out or gather together in the screened porch, at the outdoor picnic table, or in front of the huge TV in the living room.
Stayed 7 nights in Jul 2023

10/10 Excellent

Deborah P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday getaway

Visited with 4 other girls for a birthday celebration. The place was fabulous we each had our own lovely room. The place was well stocked and plenty of room to hang out together or to get a little quiet time if needed. Plenty of clean linens and towels, lots of coffee cups, wine and drinking glasses. Location is perfect. Walking distance to the town, beaches and restaurants. Bike rental and car rental nearby too. Great outdoor space too. The owner Finbarr was amazing quick to respond to any problem or questions we had and let us check out later when our flight was delayed. Would definitely recommend to others and hope to return one day.
Stayed 4 nights in Oct 2023

10/10 Excellent

Amanda B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Gorgeous home with Excellent Location

My friends and I had so much fun at Finbarr's beautiful property. It had such charming details, plenty of space for our group, and we immediately felt at home upon arrival. Finbarr was a gracious and patient host when we texted him that we had locked ourselves out. The response was prompt and resolution was quick. The keys are a little tricky and seemed like they were maybe cut a bit poorly but we eventually figured them out. We would love to come back and stay another time!
Stayed 3 nights in Jun 2024

10/10 Excellent

Alexandra C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very convenient location and lovely property

Owners were very responsive to our needs and requests
Stayed 3 nights in Oct 2021

10/10 Excellent

Bridget B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Great location, central to beach and town. Nice beach amenities and plenty of spaces for lounging. Enjoyed a great week with friends and family.
Stayed 7 nights in Aug 2021

10/10 Excellent

Karen N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun family visit

My extended family and I rented this spacious farmhouse. It was in a great location - within walking distance to town and easy to get to many places on the island. The house itself was great for our group and had everything we needed. Emily and Finbarr were very responsive. We would highly recommend!
Stayed 7 nights in Jul 2021

10/10 Excellent

Sean H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Jul 2025

About the host

Hosted by Finbarr Sheehan

Host profile image
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.

Languages:

English

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