Sleeping in a safehouse saves your game and skips six in-game hours. Most rooms also let you change outfits and use an ammo chest, and most stay yours once you unlock them. Ridgewood Farm and Plainview are rentals, not keepers.
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New Austin
Nuevo Paraíso
West Elizabeth
Which rooms count toward 100%
Every permanent room counts except Pleasance House. Ridgewood Farm and Plainview are rentals, so they never count toward 100%.
New Austin safehouses
MacFarlane's Ranch is free during the opening ranch story missions, so there's nothing to pay there. The New Austin purchases unlock as you move through the opening ranch story. Armadillo is the cheapest buy at $50, and Rathskeller Fork and Thieves' Landing cost $100 each. If you're buying early, start with Armadillo and move up to the $100 rooms.
Nuevo Paraíso: Irish's Shack and the Mexican Poncho
Irish's Shack is free once We Shall Be Together in Paradise is done. The other Nuevo Paraíso rooms are purchases: Escalera at $150, Chuparosa at $200, Casa Madrugada at $250, and El Matadero at a base cost of $150 to $300. El Matadero also has a ladder up to a roof-mounted Gatling gun.
Your first Mexican purchase unlocks the Mexican Poncho, so any of the buyable rooms will do it. At $150, Escalera is tied with El Matadero's low end.
Those are base prices. Story choices can change them, as covered under West Elizabeth below.
Pleasance House and the rentals
Pleasance House is a deed mission, not a purchase. During Water and Honesty, you can pay Clyde $200 or take the deed by force and loot it from his body. Holding the deed gives you access. Hand it to McAllister and you lose access, so kill and loot him to get the deed back and keep the house.
Rentals work differently. The shed at the east end of Ridgewood Farm and the Plainview tent cost $5 per use. Each $5 rental gives you one save-use, and neither is a permanent safehouse.
West Elizabeth: Blackwater and Manzanita Post
Blackwater's room is free once An Appointed Time is done. Manzanita Post is a purchase after the same mission, with a base cost of $400.
Spoiler: If you warn Abner in The Prohibitionist, room prices double. Manzanita Post then costs $800. If you kill him, they drop by half, bringing the cabin to $200.
Beecher's Hope rooms
The Marston ranch at Beecher's Hope gives you John's room and Jack's room, and each one is free. John's room opens after The Outlaw's Return.
Spoiler: John's room stops working as a safehouse after The Last Enemy That Shall Be Destroyed, though its ammo chest stays usable. Jack's room opens after that same mission.
FAQ
Which safehouses have an ammo chest?
Most of them. Ridgewood Farm, Plainview and Pleasance House don't have one, and Irish's Shack gives a little cash from its chest instead of ammo.