Family Compound & Large Group Rentals on Martha's Vineyard

We use compound to mean 8 or more bedrooms across one property, typically a main house plus one or two detached guest buildings (cottages, pool houses, barns). Some single-building rentals with 8+ bedrooms also qualify. The defining feature is that the entire group stays on one property without splitting across rentals.

12 to 18 months ahead is typical. The wedding-capable compounds — those with outdoor event permits, pools, lawns, and parking — are a small subset of inventory and they go first. If you have a target weekend, inquire as soon as you know the date.

Sometimes. The rental property must have a specific outdoor-event permit from the town (usually Edgartown, Chilmark, or Aquinnah). Not every compound has one. The ones that do typically have guest count caps, sound ordinance limits, and vendor restrictions. Confirm before you put down a deposit. Many groups book the compound for lodging and host the ceremony at a separate venue.

Two different numbers. A 12-bedroom compound might sleep 24 overnight (2 per room) but be permitted to host 75 people for a Saturday afternoon outdoor reception. Always ask both questions separately. Sleeping capacity and event capacity are set independently.

On a per-couple basis, compounds are often comparable or cheaper than booking 8-10 separate cottages, especially in peak season. Total compound rates run $25,000-$120,000+ per week. Divided across 16-20 adults, that often lands at $200-$600 per couple per night, which beats booking individual rentals in Edgartown.

About 95% do. Pool is essentially standard at the compound tier. The few without are typically waterfront compounds where the ocean serves as the swim. If a pool is non-negotiable, mention it from the start.

Yes, with notice. Wedding-permitted compounds expect outside caterers, bartenders, planners, and rentals. Provide the owner and rental team with your vendor list at least 60 days out. Some compounds restrict tent setups, music after 10pm, or specific vendor types — confirm before signing contracts.

Edgartown (especially West Tisbury Road and out toward Katama), Chilmark, Aquinnah, and a smaller number in West Tisbury. Up-island compounds tend to have more privacy and larger lots. Down-island compounds tend to be closer to the village and the airport.

Yes. Standard security deposits on compound rentals range from $5,000 to $25,000 depending on the property, with higher amounts for wedding events. The deposit is refundable subject to condition at checkout.

Logistically yes, but the rental contract is signed by one lead renter who is financially responsible. We see groups handle this with a single booker collecting from the group via Venmo or Zelle. The rental contract does not split across guests.