Great views can be enjoyed from this charming Bermuda home situated on a hillside in Southampton. Conveniently located near the beaches of South Shore, the closest being Church Bay, known as a great snorkeling location. Horseshoe Bay Beach is also 5 minutes away. This home has three large bedrooms with 3 bathrooms. Availability is Fall 2025, or late Spring 2026, coordinate dates with the owner after bidding closes. For more information, copy/paste this link into your web browser: www.airbnb.com/rooms/23697748 Value: $6,000.

This professionally designed & decorated vacation home is great for a quiet get away for one or two couples/families or for a multi-generational family vacation. Located on a quiet dirt road, you'll be away from the noise of downtown Oak Bluffs, but still only a ten minute walk from all the action! The house has two large master king suites on the second floor plus additional queen bedroom. The first floor has an open concept design which is perfect for entertaining, with beautiful cherry hardwood floors throughout. The dining room has seating for 8, the living room is generously sized with a beach stone fireplace. The kitchen is well equipped for gourmet cooking! Outside is a private deck and patio area, complete with fire pit and a wood-fired pizza oven. For those lazy evenings, head down to the basement, get comfortable on the large sectional sofa and watch a movie on the wide screen TV. The basement playroom is full of puzzles, games, lego's, arts & craft supplies. Right next to the playroom is a large bunk room with three sets of bunks beds and a full bath. In total, the house sleeps up to 13. Coordinate dates with the owner after bidding closes. For more information, copy/paste this link into your web browser: www.vrbo.com/513568 Value $3,500

Leave from Oak Bluffs for a 3 hour cruise to either Edgartown or Tashmoo Harbor with up to 8 people. We supply beer, wine and appetizers, you provide the fun and keep the memories! Coordinate dates with the captain after bidding closes. Value $1,500.

Juneteenth Week in the “She Shed”

In the heart of the Oak Bluffs Copeland District: A seven-night stay for up to eight(8) people in a delightful Victorian gingerbread cottage. Freshly upgraded for 21st Century comfort. Walk to everything: Inkwell Beach, Union Chapel, Circuit Avenue. Celebrate Juneteenth, Harborfest and Father’s Day! Or just kick back and enjoy the water view from the porch.

Check in: Sunday June 14, 2026
Check out: Sunday June 21, 2026

Features: 4 bedrooms – three with double beds; one with two twins.Two full baths, Heat/AC, Beach towels and chairs

No pets, no smoking, thank you. $500 refundable security deposit required. Value $5,000.

Do you love to golf? Take three of your friends out to play eighteen holes at Mink Meadows! Mink Meadows has maintained a quality and challenge on the island that is second to none, 85-plus years after its inception.

One thing that hasn’t changed over the years is the character of the club as originally envisioned. Mink Meadows continues to be an inclusive group of golfers who enjoy the diversity in every dimension of our fellow members, their guests, and public players that we welcome to the club. Mink Meadows also continues to support, and give back to, the Martha’s Vineyard community in a variety of ways. One such way includes making the course available each year to many charitable and/or non-profit organizations for various golf outings. Value: $688.

In 1980, Michael Landon hired the first black screenwriter to write an episode for his iconic series, “Little House on the Prairie,” Kathleen McGhee-Anderson. This is an autographed copy of her original script, "Make a Joyful Noise", which aired on January 26, 1981. The storyline focuses on another wonderful aspect, (rare in the 1980’s on TV, ) it’s a love story between Joe Sagan played by Moses Gunn, and Hester-Sue Terhune, Ketty Lester. A photograph from the episode is included. This is a notable, memorable piece of television history! Value: Priceless!

An opportunity to get feedback on your developing work with a celebrated, experienced professional writer, Kathleen McGhee- Anderson. She will discuss and critique your developing work, (twenty five pages/two hours) in the genres of television, film, theater, fiction or memoir. A one-on-one session on the island during the next twelve months, you have the opportunity to get feedback on a work in progress, or one you hope to embark upon in the future, which you can discuss and get coaching advice about how to start. Kathleen McGhee-Anderson is the author of “Miss Maybelline’s Flights of Fancy” on the Martha’s Vineyard Playhouse stage last summer; a television showrunner and producer, a screenwriter, “The Color of Courage,” and recently penned the best-selling memoir of one of Motown’s Four Tops, Duke Fakir, “I’ll Be There.” She’s a graduate of Spelman College and Columbia University, and has taught on the faculties of Howard University and the New School in New York City. Kathleen is busy writer, and a member of the Trustee Board, who offers her expertise in support and celebration of Union Chapel. Value: $1,000.

Ever been disappointed to have to sit outside in the hot sun on the day that Rev. Otis Moss III is preaching? Here's your chance to get four reserved front row VIP seats to the most popular Sunday of the season!

Value: PRICELESS

Don't miss this opportunity to have a 15-20 minute ride for two passengers in a bi-plane from Classic Aviators of Martha's Vineyard. See the Vineyard as the gulls and osprey do! Based at Katama Airfield in Edgartown, our biplane tours have been part of Martha's Vineyard summers for 20+ years. These open cockpit planes were once used to train military pilots and have been professionally restored to pristine condition.

Rides are available for all ages and offer a unique way to take in the Island’s views and landscapes. It’s an unforgettable experience! Value: $400

Take a threesome out to Farm Neck to golf eighteen holes! Coordinate the day/time with your donor host and the four of you will play at this beautiful course carved into a beautiful peninsula abutting Vineyard Sound. As you play, you will find yourself traversing a striking variation of topography and vegetation – everything from woodlands, to open meadows, to salt marshes, to stunning overlooks and intimate brushes with the ocean’s edge. Farm Neck has continually earned a 4 1⁄2 out of 5 star rating in Golf Digest’s “Places to Play,” and is considered by many to be one of the premiere golfing experiences in the Northeast, “A true test of golf in an idyllic setting.” Value: $990.

Enjoy a full week get away experiencing the the heart of Red Rock country of Sedona, Arizona. Set in the mist of the breathtaking desert landscape, this condo at the Villas of Sedona Resort offers easy access to local attractions and outdoor adventures. After you've explored everything Sedona has to offer, take a short drive up to the South Rim of the Grand Canyon (about a two hour drive). Imagine, you can explore one of the seven natural wonders of the world and be back at the resort by dinnertime! This is a one bedroom loft with a fireplace and is able to sleep 6, with a king bedroom, a queen murphy bed and a double sofa bed. This offer is available anytime in 2026, coordinate dates with the owner after the bidding closes. For more information on the area & resort, copy/paste this link into your web browser: https://www.villasofsedona.com/ Value: $2,500.

Score big for a great organization with two incredible seats to a Boston Celtics home game during the 2026 season! You and a guest will enjoy the electric atmosphere of TD Garden from center court in Lodge 12, Row 7— an unbeatable vantage point for any Celtics fan.

Game date to be mutually agreed upon, subject to availability. Don’t miss this chance to witness world-class basketball action from some of the best seats in the house! Value: $700

No matter who is preaching, the second Sunday in August is always PACKED. Ever been disappointed to have to sit outside in the hot sun on that day rather than be inside in the cool shade? Here's your chance to get four reserved front row VIP seats to the one of the most popular Sundays of the season! Value: PRICELESS

Love baseball?! Then bid on these 2026 season tickets for 4 adults (or children!). Includes Vineyard Sharks sweatshirt, T-shirt and hat too! This is great fun for the whole family -- don't miss this opportunity!

Value: $500.