Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.

Photo gallery for Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.

A spacious room with a large French door leading to a deck, a sofa, and a lamp on a side table.
A house with a covered porch, surrounded by a well-maintained garden with various plants and a gravel driveway.
A spacious living room with a large gray sofa, a wooden side table, and a patterned rug.
A two-story house with a covered porch, a well-maintained lawn, and a variety of flowering shrubs.
A dining area with a wooden table and chairs, a view through a glass door to an outdoor patio, and a kitchen with white cabinets and a marble countertop.

Reviews

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

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • On-site fitness center
    A rare find - enjoy convenient access to fitness facilities during your stay.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Oak Bluffs Harbor

Popular amenities

  • Patio
  • On-site fitness center
  • Toys
  • Barbecue grill
  • Air conditioning
  • Refrigerator

Explore the area

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

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

2 Twin Beds

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Lower Level has a Pull Out Couch

1 Double Futon

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Bathtub or shower · Bathtub · Toilet · Shower only

Spaces

Deck or patio
Kitchen
Outdoor play area

Add dates for prices

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About the neighborhood

Oak Bluffs

Oak Bluffs is home to this vacation home. 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.
View more Vacation Homes in Oak BluffsOpens in a new window
Map
Oak Bluffs, MA

What's nearby

  • Oak Bluffs Harbor - 8 min walk - 0.7 km
  • Circuit Avenue - 13 min walk - 1.1 km
  • Cottage Museum - 13 min walk - 1.1 km
  • Oak Bluffs Town Beach - 18 min walk - 1.5 km
  • Inkwell Beach - 3 min drive - 1.5 km

Getting around

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

Restaurants

  • ‪Lookout Tavern - ‬20 min walk
  • ‪Nancy's - ‬17 min walk
  • ‪Portuguese-American Club - ‬14 min walk
  • ‪Nomans - ‬5 min drive
  • ‪Biscuits - ‬17 min walk

Frequently asked questions

Is Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB. pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.?

As of Oct 31, 2026, prices found for a 1-night stay for 2 adults at Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB. on Mar 1, 2027 start from $685, 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?

Onsite parking is available at the property.

What time is check-in at Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.?

Check-in begins at 4:00 PM.

What time is check-out at Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.?

Check-out is at 11:00 AM.

Where is Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB. located?

Situated in Oak Bluffs, this vacation home is within a 15-minute walk of Martha's Vineyard Hospital Development and Martha's Vineyard Hospital. Oak Bluffs Public Library and Oak Bluffs Harbor are also within 1 mi (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 27 out of 28 reviews
Rating 8 - Good. 1 out of 28 reviews
Rating 6 - Okay. 0 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Incredible stay!! Jason was very communicative, and super helpful ensuring this house worked for our stay. Check in was easy, and everything was as was shown in the VRBO post. Would absolutely stay here again and recommend to anyone coming to the island.
Stayed 5 nights in Sep 2026
Response from Management on Oct 17, 2026
Katy, we were more than happy to share details regarding the house before and during your stay. We understand how important it is to plan ahead, especially when you have a milestone family event on island, and many other family members who are also here to celebrate. I am so happy to hear that the house met your needs and expectations. Hope to see you and your family again soon! Sincerely, Jason
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful property. Exceptionally beautiful, clean and with many amenities including bikes, cornhole, beach chairs and towels, etc. Would definitely return. Jason is a great host and responds quickly.
Stayed 7 nights in Aug 2026
Response from VrboOwner on Sep 15, 2026
It was a pleasure having you and your family as guests. Thank you for mentioning all of the amenities. We just try to make each stay fun and enjoyable for everyone. It would be wonderful if you choose to stay with us again next year!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved this smartly laid out and beautifully landscaped home.We were delighted to find the house immaculately clean, the bedding plush and the towels extra thick. Furnishings are modern and well thought out. The quality is evident everywhere you look.The location is completely private and yet town and restaurants are easily walkable. Jason was a perfect host - friendly, informative and easily accessible. We would return to this home without hesitation!
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family of five. Loved our stay at this house. Jason is a great host and very responsive. Location is very good in Oak Bluffs. We often walked to town and back. Good access to other parts of the Island too. Beautiful landscaping :)
Stayed 5 nights in Jun 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a beautiful home and location! The pictures are spot-on and the location was serene and quiet. There were some issues with the lawn irrigation system noise impacting my sleep but, after 2 nights, most of it was resolved. Jason was extremely responsive from both a communication as well as a solution perspective. Lots of space for friends and family to spread out in while also being so close to the center of Oak Bluffs.
Stayed 3 nights in May 2026
Response from VrboOwner on Jun 29, 2026
I am happy to hear that you enjoyed the home and location, yet regretful that our landscaper missed setting the irrigation timer from early morning to late morning. You were with us for only 3 nights and I understand how important each night of rest can be if the low volume sound can be heard. Our landscaper was so busy early season that he promised but missed coming the same day, and adjusted the settings the following day. Thanks for accepting our refund, and offer to stay with us on your birthday in October. All the best, Jason
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This a beautiful property that would be ideal for a large family or a group of friends. Bedding is great and the host was extremely helpful and easy to communicate with. This was one of the best properties we have stayed in while using VRBO.
Stayed 3 nights in Sep 2025
Response from VrboOwner on Jun 29, 2026
Thank you for your feedback. We always ask ourselves, "would we want our host to be responsive and communicate when we go on vacation?" Thanks again and hope to see you again next year! Best regards, Jason
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Check in was easy. Pleasant walk to OB. kitchen was nicely stocked and equipped.
Stayed 6 nights in Jul 2025
Response from VrboOwner on Aug 5, 2025
Hi Camille, thank you for your kind words. Well, we almost ensured a perfect stay. Thanks for the call and we were happy to have our caretaker provide the attention needed within the hour. Although we live off island, we have a friendly team of caretakers whom we value and trust immensely.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay at this Oaks Bluffs home was absolutely wonderful. From the moment we arrived, we felt like we had found our own peaceful retreat on Martha’s Vineyard. The property is beautifully landscaped, with lush gardens and inviting outdoor spaces that made it easy to relax and unwind.The location offered the perfect balance of privacy and convenience, quiet enough to feel like an escape, yet just a short drive or bike ride to everything the island has to offer.What truly set this experience apart was our host. Jason was incredibly responsive, thoughtful, and easy to communicate with throughout our stay. Every question was answered promptly, and it was clear that Jason genuinely cared about making sure we had a great experience.If you are looking for a serene, and well-maintained home with an outstanding host, this is it. We would not hesitate to stay here again and highly recommend it to anyone visiting Martha’s Vineyard. Five stars all around!
Stayed 7 nights in Jul 2026
Response from VrboOwner on Aug 11, 2026
This is just a wonderful review! Thank you very much. It is such a pleasure to share our home with wonderful families. Hope to see you again very soon!
Verified review

10/10 Excellent

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

Perfect weekend

Jason was super communicative, the place was spotless, peaceful and perfect! Easy walk to town. Definitely recommend!
Stayed 3 nights in Jun 2025
Response from VrboOwner on Aug 5, 2025
Thank you, Catherine! It was our pleasure having you and your family as guests. We definitely ask ourselves, “how would we like to be treated?” I am glad to hear that our communication met your expectations. Hope to see you again soon!
Verified review

10/10 Excellent

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

Charming in Martha’s Vineyard

This home is as advertised: clean and quiet, with an easy drive to Oak Bluffs. Jason was a pleasure to work with and I’d definitely stay here again.
Stayed 3 nights in May 2023
Response from VrboOwner on Jun 9, 2023
Dear Katisha, Thank you for your review! I am so happy to hear that you and your family had a great stay at the Panola House. We look forward to our next stay with us. Best regards, Jason
Verified review

10/10 Excellent

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

Jennifer T

We had a great stay, besides the weather, but house was extremely clean and comfortable for our visit. Jason was a super host!
Stayed 3 nights in Sep 2023
Response from VrboOwner on Jul 26, 2024
Jennifer, thank you for sharing how much you enjoyed your stay at the Panola House. We hope to host you and your family again in the future.
Verified review

10/10 Excellent

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

Excellent

Loved it
Stayed 5 nights in Jun 2023
Response from VrboOwner on Sep 13, 2023
Thank you, Patrick! You and your family have been fantastic guests. We will see you again next year! Best regards, Jason
Verified review

10/10 Excellent

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

Great property!

My husband and I stayed here with our 3 kids ranging in ages 16-infant. We really enjoyed the privacy of the lot this beautiful house is on. The house had everything we needed and there was more than enough room for us. Jason is a great host and ensured we had everything we needed for our stay. We would love to come back some day.
Stayed 4 nights in Jul 2024
Response from VrboOwner on Aug 20, 2024
Hi Ashley, we are so happy to hear that your family enjoy the house and property. We were drawn to the privacy as well. It is a great place to connect with family and friends, while staying close to the beach, campgrounds, and Circuit Avenue. Hope to see you again next year! Sincerely, Jason
Verified review

10/10 Excellent

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

Oak Bluffs Retreat

Beautiful property- set back from the street down a quaint road in the woods, yet has an impeccable yard and open feel with round about driveway paved with shells. Home is in immaculate condition and well stocked It is a bit of a trek to town but the walking trail there is gorgeous and easy to hit steps each day Very helpful host who made us feel at home and clearly prioritizes the guests’ experience Anyone who wants to stay in Oak Bluffs area should surely consider this propertyq
Stayed 3 nights in Jul 2025
Response from VrboOwner on Aug 5, 2025
Hi Kathryn, thank you for staying with us and for your very positive review! My wife just mentioned to me this morning, “did you know so many people walk that way?” She happened to meet an old friend for the first time along the way :)
Verified review

10/10 Excellent

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

Sister Weekend Getaway

My three sisters and I had a wonderful long weekend getaway. The house was the perfect setup for the 4 of us and Jason was great to work with. We loved the front porch for coffee in the morning and chatting late into the evening. It was a quick 10 minute bike ride into Oak Bluffs and Vineyard Haven so we didn't miss having a car at all. We would definitely stay there again!
Stayed 3 nights in Jun 2024
Response from VrboOwner on Jul 26, 2024
We were so happy that you chose the Panola House for your family retreat in the Vineyard. The front porch is certainly the perfect place to have conversations with family and friends. Happy to hear that you were able to bike to the beach, shops, and restaurants.
Verified review

10/10 Excellent

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

Great home, Great hospitality!

Jason is a terrific host! The home is better in person than advertised. It was the perfect amount of space for our family and friends and has all necessary amenities and tools for fabulous cooking and entertaining. And the backyard is gorgeous! I will be back!
Stayed 7 nights in Aug 2024
Response from VrboOwner on Aug 21, 2024
Karen, thank you so much for your review! We love to hear that you enjoyed the house as much as we do. The backyard feels like an oasis to us. Great place to start and end the day on the Vineyard. Hope to see you again next year :)
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was truly one of the best family trips we’ve had and Panola House was a huge part of what made it so special.From the beginning, Jason was welcoming, accommodating and incredibly communicative. He even helped us with our ferry tickets months before our trip which set the tone for the care he puts into hosting.The house just feels good. It was spotless, beautifully cared for and had everything we needed. We settled in almost immediately. For our family of 6, there was plenty of room for everyone to have their own space while still having great spaces to be together. The kids loved the lower level for movie nights, and the sound system throughout the house was a favorite!We especially loved the outdoor space. Slow mornings in the backyard, sitting on the front porch and watching the turkeys pass by became part of our routine. The house gives you privacy without feeling secluded, and you’re still close to everything. We walked to Circuit Avenue in about 15 minutes.The bikes, beach chairs and towels made our beach days so easy. One of my favorite memories was watching my daughter learn to ride a bike on one from the shed!More than anything, Panola House felt like home. That’s rare when you travel and we didn’t take it for granted. Thank you Jason for sharing such a special place with our family. We’ll definitely be back!
Stayed 8 nights in Aug 2026
Response from VrboOwner on Sep 2, 2026
“The house just feels good” has to be one of our most valued compliments. We look forward to seeing you and your family again next year!
Verified review

10/10 Excellent

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

As advertised

My family of five (three kids - 15, 12 and 9) stayed here for a week and it was perfect for us. It was incredibly clean with enough space for all. We loved the location - great for walks or bike rides. The owner was very responsive and helpful (and even set up our roundtrip ferry for us). Plenty of beach chairs, towels etc. so everything was very convenient. We hope to come back in the future!
Stayed 7 nights in Aug 2024
Verified review

10/10 Excellent

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

Magical Stay!!

I couldn’t have asked for better accommodations. The home was clean, beautiful, comfortable and well stocked. The basement was awesome for the teens since they had their own space to hangout away from the adults. The walkable location was perfect and Jason responded immediately to my questions. My favorite part was watching the deer family in the mornings while having my coffee on the gorgeous porch. Magical!!
Stayed 8 nights in Aug 2023
Response from VrboOwner on Sep 13, 2023
Thank you for your wonderful review, Connie! We are so happy to hear that the Panola House exceeded your expectations. We look forward to having you and your family with us again next summer. Best regards, Jason
Verified review

10/10 Excellent

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

Great house for a family or two

We loved the house. It is a five minute drive to oak bluff and maybe 10 minute drive to Vineyard Haven. In short, great location. The house is modern and clean. Everything worked great. The yard is awesome. We played corn hole and relaxed out back. They have bicycles for the family which was fun. But I’m glad we had a car. We had five people and the house had room for plenty more. Would highly recommend and would come back again.
Stayed 4 nights in Jun 2023
Response from VrboOwner on Sep 13, 2023
Thank you for your review, Scott! I am so glad that you were able to enjoy the backyard, landscaping, outdoor games, and bicycles. Thanks again for recommending the Panola House. We hope that you decide to stay with us again in the future! Best regards, Jason
Verified review

10/10 Excellent

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

Beautiful home, comfortable stay!

This home is exceptional! All of the details have been taken care of from cleanliness to comfort to entertainment and landscaping. The spacious deck was perfect for having breakfast and watching the wild turkeys pass by. The front porch was ideal for afternoon reading and napping. The house feels light and airy and the dual thermostats and basement air conditioner kept everyone happy. We also utilized the built-in wireless speaker system to play music throughout the house. We were even able to store our 4 bikes in the spacious shed (which also contained 4 bikes and beach supplies). It was easy to bike anywhere and to walk into Oak Bluffs and Inkwell Beach. We wish we could have stayed longer, but we made many wonderful memories there!
Front drive with landscaped circle
Path to the front door
Back deck with seating and grill. Shed and trash container in background
Living room and kitchen entry
Stayed 7 nights in Jul 2025
Response from VrboOwner on Aug 9, 2025
Hi David, I hope all is well. I wanted to let you know that I gave you all 5 stars. However, for some reason, VRBO registered one category as 4. I’ve been working on having this changed to all 5’a. They are absolutely the worst with requests outside of the norm. However, it’s been escalated several times. Sorry for this. Honestly, I do not know what happened after I selected all 5’s. It’s happened twice (some glitch in their system or my app) and I am too happy about it. I’m on it :)
Verified review

10/10 Excellent

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

Responsive and considerate communication and oversight

Anytime you are invited to tell a property owner how your stay might be better is a great sign that your stay will be first rate. Jason not only asked what we needed to improve our 3 week stay, but quickly provided the drip coffee machine and blender that we suggested. Beach chairs, beach towels and umbrellas were plentiful. Two adult bicycles were available. Air conditioning was a godsend during the heat wave. Proximity to Oak Bluffs and Vineyard Haven also a huge plus. Would probably return next summer
Stayed 21 nights in Jul 2022
Response from VrboOwner on Aug 26, 2022
Thank you so much, Cliff. Our goal has always been to build rapport with great people and extended families who enjoy the Vineyard as much as we do. Our second goal continues to be focused on ensuring that you have a wonderful stay at the Panola House. It is so great to hear that your 3-week stay exceeded your expectations. You got to know the house and convenient walking location very well during your stay. Your communication with me from planning to departure was also extremely helpful and appreciated as well. See you next year, Cliff! Best regards, Jason
Verified review

10/10 Excellent

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

Fantastic time

We booked this house somewhat late into the season and got extremely lucky. The house was beautiful, well-maintained, and well-stocked. We weren’t able to get our car on the ferry because of our last minute plans, but it worked out okay. We brought bikes and the owner also had bikes for guests. We were able to get around with bikes and the bus shuttle without a problem. Also, walking to downtown Oak Bluffs only took about 20 minutes and was a pleasant walk. Overall, I really appreciated how private the property was and how well stocked the house was, especially considering we weren’t able to bring much on the ferry. There were beach towels, a beach blanket, plenty of bath towels and bedding, beach toys (for my three year old), all the necessary kitchen supplies, an iPad, and the list goes on. The owner also checked in with us to make sure we were doing okay… I can’t recommend this property highly enough.
Stayed 5 nights in Aug 2022
Response from VrboOwner on Sep 1, 2022
Thank you very much for your review, Alicia! It was great to hear that the house accommodated your entire family, especially your little ones. I must admit that when I purchased the beach toys at the beginning of the summer, I remembered when our own kids spent hours playing at the beach. Glad all worked out and that you enjoyed your stay. Hope that you decide to stay with us again next year. Sincerely, Jason
Verified review

10/10 Excellent

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

Stunning home! Great layout for families.

We were blown away by the property! Not only was it well styled and beautiful, everything was top of the line quality and the home was immaculate. The amount of natural light pouring in to the first floor was exceptional and made the overall experience in the home feel really fresh and calm. The backyard and basement were perfect for kids and adults. So much space for our very active kids to run around and play games while us adults could comfortably watch them without sacrificing our own quality comfort. Jason, our host, was everything I hope to have in all future hosts. Friendly, accommodating, reachable and helpful. He went out of his way to make sure we had everything we needed to make the most of our stay. He had the shed stocked with bikes, beach gear and lawn toys, which was an unexpected surprise. And all of it was top of the line! I wouldn’t have changed a single detail of the house and I highly HIGHLY recommend the property!
Stayed 3 nights in Jul 2022
Response from VrboOwner on Jul 31, 2022
Hi Natalie, Thank you for your review! You and your family were our very first guests at the Panola House, so your stay was special to us. My wife and I had a vision to share our home with families, such as yours, who would like to enjoy all the Vineyard has to offer. Please think of us on your next trip to Martha's Vineyard. Your family and friends are always welcome! Best regards, Jason
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Jason was extremely communicative and helpful during our stay. The house is exactly as the photos and reviews say it is - really beautiful. House was close to town, came with beach gear. Not to mention beautifully landscaped. Would stay here again!!
Stayed 4 nights in Jul 2026
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