CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

Photo gallery for CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

A living room with a fireplace, a sofa, a coffee table with a vase of flowers, and a television.
A row of white buildings with a sign reading "Union Street."
A marina with multiple boats docked at sunset.
A white wooden archway leading to a house with a porch, surrounded by lush greenery.
A covered porch with wicker furniture, a grill, and a view of a wooded area.

Reviews

9.6 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Onsite parking available
    Convenient and secure on-site parking, a rare amenity in the area.

Popular amenities

  • Balcony or patio
  • Toys
  • Barbecue grill
  • High-speed internet
  • Washer/dryer
  • Onsite parking available

Explore the area

View in a map
Oak Bluffs, MA
  • Place, Eastville Beach
    ‪6 min walk‬
  • Place, Oak Bluffs Harbor
    ‪3 min drive‬
  • Place, Circuit Avenue
    ‪3 min drive‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪19 min drive‬

Rooms & beds

5 bedrooms (sleeps 9)

''East Chop'

1 Queen Bed

'Eastville'

1 Double Bed

'The Inkwell'

2 Single Beds

'Vineyard Harbor'

1 Single Bed

'West Chop'

1 Queen Bed

2 bathrooms

1st Floor FULL Bath

Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only

2nd Floor FULL Bath

Towels provided · Bathtub · Toilet

Laundry Room

Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden

Add dates for prices

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About the area

Oak Bluffs

Located in Oak Bluffs, this holiday home is near the beach. The area's natural beauty can be seen at Inkwell Beach and Cape Cod Beaches. Flying Horses Carousel and Island Cove Adventures are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and mountain biking nearby.
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Map
Oak Bluffs, MA

What's nearby

  • Eastville Beach - 6 min walk - 0.6 km
  • Oak Bluffs Public Library - 18 min walk - 1.5 km
  • Oak Bluffs Harbor - 3 min drive - 2.2 km
  • Circuit Avenue - 3 min drive - 2.2 km
  • Cottage Museum - 3 min drive - 2.2 km

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 14 min drive

Restaurants

  • ‪Lookout Tavern - ‬3 min drive
  • ‪Nancy's - ‬2 min drive
  • ‪Portuguese-American Club - ‬13 min walk
  • ‪The Black Dog Tavern - ‬2 min drive
  • ‪Biscuits - ‬2 min drive

Frequently asked questions

Is CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS?

As of 30 Oct 2026, prices found for a 1-night stay for 2 adults at CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS on 12 Jun 2027 start from £2,768, 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 CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS?

Limited spots are available.

What time is check-in at CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS?

Check-in begins at 4:00 PM.

What time is check-out at CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS?

Checkout is at 10:00 AM.

Where is CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS located?

Situated by the sea, this holiday home is within a 10-minute walk of Martha's Vineyard Hospital and Eastville Beach. Martha's Vineyard Hospital Development and East Chop Light are also within 1 mile (2 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 29 out of 37 reviews
Rating 8 - Good. 8 out of 37 reviews
Rating 6 - Okay. 0 out of 37 reviews
Rating 4 - Poor. 0 out of 37 reviews
Rating 2 - Terrible. 0 out of 37 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.4/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property is in a great location and convenient to everything we needed for our stay. The owners responded quickly and were very kind about any requests.
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great home base to explore Oak Bluffs, Vinyard Haven and beyond. It has a summer camp meets grandmas house vibe that works very well once you settle into it.You don't really need a car but a bike/scooter/moped makes things much easier. The busses can be fickle and won't stop when at capacity.Overall a great value in an overpriced area
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay. Host was extremely responsive and the thank you note and chocolate welcome was a nice touch. Our beds were comfortable, everyone slept well. The kitchen was well stocked with for all our basic needs. House is old but definitely charming. The front porch was the real gem of the house. We all preferred the newer outdoor shower. Parking is tight for two SUVs and you are entering and exiting on a very busy main road. Otherwise, location was great given easy access by bus, bike and car to central Oak Bluffs and Vineyard Haven.
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

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

Great space!

We enjoyed our stay! It was a great, clean space with plenty of room for our family. Location was ideal, located between Oak Bluffs and Vineyard Haven.
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

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

The Wrap Around Porch Is EVERYTHING

We had such a wonderful stay. Thank you.
Stayed 14 nights in Jun 2025
Verified review

10/10 Excellent

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

Amazing home and great host!

This home was absolutely beautiful. In a great location to get anywhere in the island. The host was extremely helpful when needed. I would one hundred percent recommend this place to anybody!
Stayed 6 nights in Aug 2024
Verified review

8/10 Good

Very nice and comfortable

Nice place, only issues we had were getting wet from sprinklers always on.
Stayed 7 nights in Aug 2018
Response from VrboOwner on 2 Apr 2020
I'm glad you enjoyed your stay and we appreciate you taking such good care of the house! Thank you for letting us know about the sprinklers. We had a timer go bad, which has been replaced. We apologize for any inconvenience this may have caused you.
Verified review

10/10 Excellent

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

Great home for family

The property was great with nice big yard for games. The kitchen had little counter space but it we worked around that. The front porch was amazing for sitting down for dinner and after a long day at the beach. Everything was very clean and the cottage feel of the decor is exactly what the Vineyard is about.
Stayed 7 nights in Jul 2021
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We are a family of 8, and this home had enough room for everyone. It is an older home and has the charm and some of the wear of an older home. The kitchen had everything and the front porch was our favorite place to have dinner and spend the evening. We loved watching the rabbits and deer on the lawn. The downstair shower was clean but close.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

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

Great Rustic, Quirky MV Home

My friends and I loved staying at Eventide even though the house is fairly rustic and probably needs some updates. But if you don't mind the age, you can really enjoy the charms of the home, which includes a massive wrap-around porch, and a great location, only a short drive to Oak Bluffs, but still far enough from crowds that it's relaxing and serene. Just be careful getting in and out of the shower on the first floor and you'll do great!
Stayed 7 nights in Jul 2021
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family had a wonderful time staying in this historic home. The owners and their son, Michael, were so accommodating and responsive throughout the entire stay. The home was immaculate and fully stocked with everything we needed for preparing meals at home. The history of this centuries old home was so interesting and made the stay more charming. It's really a 5 star stay, however, renters should know this is a very old (200yrs!) home with not many modern cosmetic upgrades. The home has AC in all the rooms upstairs and one unit downstairs - all worked perfectly well. However, the bathrooms and kitchen, (while function perfectly well) could use a make-over. I think cosmetic make-overs in the kitchen and bathrooms wouldn't detract from the historic charm. For elderly guests or guests with limited mobility, the clawfoot tubs would be difficult to navigate. There is only one shower inside the house, located downstairs. There is a basic walk-in shower located in the laundry shed, but it definitely feels like showering in a shed. The house is also located on a very busy road with tight parking for two vehicles - it was tricky pulling in/out, but we eventually got the hang of it.All in all, this is a great, historic home in a good location, supplied with everything you need for a fun family Vineyard stay. Perfectly immaculate and again, the owners were wonderful to engage with. Great home, just know it's simple in appointments and amenities, but fully functional.
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
If you love and have patience for old homes with character, this one is for you. If you like sleek and modern, this might not be it.Our crew had mixed feelings going in but the house very much grew on everyone. The bathroom situation was most challenging because people do not like baths but everyone learned the gift of outdoor showering.The kitchen was also hard to prepare food because of lack of counter space but we made it work.This house has 5 bedrooms, a massive porch and massive outdoor space. Everything one could want. And the pantry is WELL stocked. We were shocked to find things like pineapple corers and eggs slicers. We had a lovely time.
Stayed 7 nights in Aug 2025
Archival

10/10 Excellent

Memorial Day Girls Weekend

Working with Dana at Eventide provided a seamless booking experience; he was always available to answer any questions we had, and provided excellent instructions for getting to/into the house. We booked Eventide for Memorial Day Weekend as a group of 9 girls. We had no complaints all weekend, and the home provided a great central point for us to come home to after going off and doing our own thing. There was plenty of space to spread out and find privacy if we needed it, and great communal areas for meals and games. There was only 1 shower, but it never presented a problem, even with a group of 9 women! The ammenities provided were enough so that we never even needed to leave the house if we didn't want to. The location was excellent; 15 minute walk to OB and 20 minute walk to VH. It is also on the bus line for the 13, so getting anywhere from VH all the way to Edgartown is very easy. The taxi's were also able to find it easily, so we had no problem getting to the house off the ferry in the dark. It rained all weekend, but the front porch offered enough room to hang out and play games without getting rained on. There is plenty of yard space, and it is secluded by a nice row of trees and a fence. We would all highly recommend Eventide, especially for a girls weekend or family getaway, and are very much looking forward to returning next year! A great weekend spent on the Vineyard! Thanks, Dana!
Response from VrboOwner on 2 Apr 2020
There are two (2) indoor showers: one in the first floor bathroom, the other in the laundry room. There's also a 3rd shower, outdoors. .
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We thoroughly enjoyed our girls’ trip! The home was spotless, comfortable, and conveniently located along the bus route, making it easy to get around. We especially loved relaxing on the beautiful wraparound porch, where we spent a lot of our time. We did have a minor issue with one of the air conditioning units, but the hosts responded quickly and resolved it promptly. Overall, we had a wonderful stay and would happily recommend this home to others.
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. Just a few minutes drive to Oak Bluffs and Vineyard Haven. Really enjoyed the porch and large yard. Rooms were very clean, albeit buggy, which is probably unavoidable in an older home. We would definitely stay here again!
Stayed 7 nights in Jun 2026
Response from VrboOwner on 26 Jun 2026
Hi Anne. We're glad you enjoyed your stay and thanks for taking great care of the place while you were there. I'll be reaching out to you for more information if you'll kindly provide it so that we can properly address what you saw. We appreciate the honest feedback and take it very seriously. Thanks again for staying at Eventide and we hope you'll visit us again!
Verified review

10/10 Excellent

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

Great Location and Host

This home is in a great location—nestled perfectly between oak bluffs and vineyard haven. Plenty of outdoor space for families to relax and enjoy. The Bowers family is incredibly responsive and kind. Look Forward to staying here again.
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

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

Great stay in East Chop

My family (grandparents, parents, and children) stayed here. It's a great place for kids because they have such a big yard to play in. While the streets are busy near the house there are trails that make it easy and safe to walk to Vineyard Haven. It seems like the bike trail extension will go right past the house, which will make this property even more of a wonderful stay. If you are a person who likes everything new and updated (bathrooms/kitchen), then this isn't the place for you. But if you are a lover of old houses, this is the perfect fit. Everything worked well, and we found there were plenty of showers (3!!! plus a tub upstairs). A great property. And the porch is just amazing.
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

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

Great value and comforr

Nicely furnished, large deck for outdoor dining, didn’t use but outdoor games for kids and conveniently located.
Stayed 6 nights in Aug 2021
Verified review

10/10 Excellent

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

Very accommodating owners and well sticked rental

Quite positive
Stayed 14 nights in Aug 2021
Verified review

8/10 Good

Liked: Communication, location, listing accuracy

Good spot for families with little kids

Home has a large yard and amazing porch and it is "little kid" walking distance to a small beach. It is not the spot for adults to entertain other adults inside - but a family with children who like to play outside will find everything they need.
Stayed 7 nights in Aug 2021
Verified review

8/10 Good

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

Nice Stay at Eventide

Overall the house was very good. The yard and porch were fantastic; it's where we spent a majority of our time when there. The kitchen was small with little counter space but we made do and the living room was great. Bedrooms upstairs were a good size. We did wish there was a shower in the upstairs bathroom though. It's big enough! We ended up taking all of our showers in the outside shower which was nice anyway (if a bit narrow). We really enjoyed sitting outside on the fabulous porch at night but one thing that we never quite got used to was the very loud and busy intersection where the house is located. Still it was a very enjoyable stay.
Stayed 7 nights in Jul 2021
Verified review

8/10 Good

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

Great stay

We enjoyed our stay at Eventide and Martha’s Vineyard. Rooms were very comfortable, plenty of closet space given the age of the property and ample storage, wonderful yard with lots of space for games. The porch was a perfect place to read, have coffee, outdoor meals, nap, whatever you like. Dana and Tina were friendly and accessible for any questions we had. The road does gets a bit loud but the air conditioning drowns out a lot. Good location- not too far nor too close to the action of Oak Bluffs. Quick walk to small beach and about 15-20 min walk to Vineyard Haven. Thank you Dana and Tina!
Stayed 7 nights in Jul 2021
Verified review

10/10 Excellent

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

Perfect island getaway for the Family

Home had everything that our family needed for a beach vacation. Kitchen was well stocked. Porch was charming and excellent to have meals on or just read a book. Yard was perfect for lawn games and house was centrally located between Oak Bluffs and Vineyard Haven and a small beach just a short walk down the road. Great memories were made for our 2021 vacation.
Stayed 7 nights in Jun 2021
Verified review

10/10 Excellent

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

Perfect!

Eventide was exactly what we needed and more! The location was perfect for us being so close to Oak Bluffs and Vineyard Haven centers. We walked, biked and drove as needed, and it was great to have those options. Although the location is on a busy corner, you feel very secluded with the large beautiful hedges and fences providing complete privacy. We could see the water from our upstairs bedroom windows and could take a short walk to a small beach area to fish and skip rocks, etc. such a treat! The house itself was so beautiful, which we saw from the pictures online, but we were so pleasantly surprised at the quaintness inside. It was nostalgic and comfortable, with such character! We fell in love with it. We have rented several houses on the island and this is our definite favorite. It was spacious, cool on hot days, and very well-stocked and furnished. The porch was our favorite part of the house. It is so big and absolutely gorgeous! We enjoyed so much quality time as a family on the porch, visiting, eating, playing games, etc. Between that and the spacious lawn, the property was ideal for a family vacation. The owners were so nice to work with; communicative and very responsive. We highly recommend renting this very special house on this island that is so close to our hearts. We can’t wait to return!
Stayed 7 nights in Jun 2021
Verified review

10/10 Excellent

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

Fantastic weather and fantastic family property!

This was the perfect home for my family! This spacious 5 bedroom allowed for my entire family to be comfortable. The window AC’s are a must on the Vineyard during this time of year, and something we were grateful to have in all of the upstairs bedrooms. The kitchen had every thing I needed and it allowed me to prepare home cook meals, as if I were in my own kitchen. We so enjoyed the wraparound porch. The seating area was perfect for sleeping, reading or any kind of lazy beach socialization. Breakfast, lunch and dinners we served on the outside round dining table! My favorite - the outside shower! There is nothing better than taking a warm shower under the stars. We took advantage of every outdoor amenity this beautiful beach home had to offer! The property is located at a busy intersection, across the street from the MV hospital, so the traffic and siren noise can be challenging, but we quickly got used to it. So many other positives to this VRBO home outweigh this minor distraction. The Bowers have created a well appointed beach home - we plan to stay here in the future! A gem on a gem of an island! .
Stayed 7 nights in Sep 2020
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